Name: 5335-87-5|1,2-Bis(4-methoxyphenyl)disulfane|98%
Brand: Ambeed
SKU: A476237
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[ 696-63-9 ]
[ 5335-87-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	In chloroform at 20℃; for 0.0833333h;
100%	With di(p-methoxyphenyl) telluride; 5,10,15,20-tetraphenyl-21H,23H-porphine In dichloromethane at 0℃; for 0.25h; Irradiation;
100%	With dihydrogen peroxide; sodium iodide In ethyl acetate at 20℃; for 0.5h;

100%	With C₂₆H₅₀N₁₂⁽²⁺⁾*2F₆P^(1-) In acetonitrile at 20℃; for 1.5h;
100%	With (S)-tetrahydrotellurophen-3-amine hydrochloride; dihydrogen peroxide In dichloromethane at 25℃; Flow reactor;
99%	With copper(II) nitrate In propan-2-one Ambient temperature;
99%	With 1-n-butyl-3-methylimidazolium methylselenite at 60℃; for 3h;	General procedure for the oxidation of thiols with [bmim][SeO₂(OCH₃)]: Method A: In a Schlenk tube under open atmosphere and at room temperature, the corresponding thiol (1.0 mmol) was added to [bmim][SeO2(OCH3)]10 (1.0 mL). The reaction mixture was allowed to stir at 60 °C for the time indicated in Table 1. The progress of the reaction was monitored by TLC. Method B: In a 10 mL glass vial equipped with a small magnetic stirring bar, containing 1.0 mL of [bmim][SeO2(OCH3)] was added the thiol (1.0 mmol). The vial was tightly sealed with an aluminum/Teflon crimp top. The mixture was then irradiated in a microwave reactor (CEM Explorer) for the time indicated in Table 2 at 30 °C (temperature was measured with an IR sensor on the outer surface of the reaction vial), using an irradiation power of 100 W and pressure of 150 psi. After the reaction was complete, the product was extracted by successive washings with petroleum ether (3 × 5 mL), dried over MgSO4, and concentrated in vacuum. The residue was purified by column chromatography on silica gel using ethyl acetate/hexanes as the eluent.
99%	With dihydrogen peroxide In lithium hydroxide monohydrate; acetonitrile at 20℃; for 0.5h; Green chemistry; chemoselective reaction;	2.3. Typical procedure for selective oxidation of thiols to disulfides General procedure: In a typical oxidative coupling reaction, 2 mmol thiophenol was dissolved in acetonitril (3 mL). Then 0.03 g (0.02 mmol) catalyst and 0.25 g hydrogenperoxide (30% aqueous) were added. The reaction mixture was stirred for the various reaction times as indicated in Table 2. After the completion of the reaction (determined by TLC), which is associated with precipitation of disulfide and elimination of thiol odor. The catalyst was separated by filtration, washed with ethyl acetate and heated at 60 °C prior to its reuse in the next reaction. The combined organic filtrates were then washed with water and the organic layer separated and dried over magnesium sulfate. The product was obtained after removal of the solvent. The conversion was determined by isolated yield and compounds were characterized by 1H and 13C NMR. In most cases, the products could be isolated in their pure forms by simple filtration and evaporation of the solvent.
99%	With N,N,N,N,-tetramethylethylenediamine; oxygen; Eosin In ethanol for 0.333333h; Irradiation;
99%	With cobalt(II)phthalocyanine-tetra-sodium sulfonate In lithium hydroxide monohydrate at 60℃; for 6h; Schlenk technique;
99%	With sodium perborate monohydrate; glacial acetic acid In lithium hydroxide monohydrate at 20℃; for 4h;
98%	With aluminum(III) oxide; sodium periodate In hexane at 20℃; for 0.5h;
98%	With lithium hydroxide monohydrate; dihydrogen peroxide In various solvent(s) at 20℃; for 0.166667h;
98%	With lithium hydroxide monohydrate; bromine; mesoporous silica In dichloromethane
98%	With iodine In lithium hydroxide monohydrate; acetonitrile at 20℃;
98%	With oxygen; vanadium(V) oxytrichloride In ethyl acetate at 20℃; for 66h;
98%	With cerium(III) trichloride; iodine; pyrographite In ethyl acetate at 20℃; for 0.9h;
98%	With silica supported cobalt(II) tetrasulfophthalocyanine In ethyl acetate at 20℃; for 1.5h;
98%	With aluminum(III) oxide In neat (no solvent) for 0.25h; Milling; chemoselective reaction;
98%	With 3,6-di(2'-pyridyl)-1,2,4,5-tetrazine In ethanol; lithium hydroxide monohydrate at 40℃; for 0.166667h;
98.33%	With oxygen In acetonitrile at 60℃; for 12h; Schlenk technique;
98%	With potassium-t-butoxide In tetrahydrofuran at 25℃;
97%	With bromine; Potassium bicarbonate In dichloromethane
97%	With air; iron(III) chloride; sodium iodide In acetonitrile for 0.583333h; Ambient temperature;
97%	With dimethyl sulfoxide at 90℃; for 6h;
97%	With oxygen; anhydrous sodium carbonate; 1-n-butyl-3-methylimidazolium tetrafluoroborate at 20℃; for 0.5h;
97%	With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 0℃; for 0.0833333h;	4.2. General procedure for the synthesis of disulfides Procedure for symmetrical molecules: DDQ (0.5 mmol) was added to an ice-cooled solution of thiol (1 mmol) in dichloromethane (3.0 mL). The reaction mixture stirred for 5 min at 0 °C and monitored by TLC analysis. The reaction mixture was concentrated under reduced pressure and directly purified by column chromatography by gradient elution of ethyl acetate in hexanes to give the title compounds.
97%	With graphite oxide In chloroform at 100℃; for 0.166667h;
97%	With bovine serum albumine In lithium hydroxide monohydrate at 20℃; for 14h; Enzymatic reaction;	2.3.1. General procedure for the synthesis of disulphides (1b-27b) Thiophenol (0.25 mmol), BSA (50 mg) and deionized water(600 L) were stirred at room temperature for 12 h or till com-pletion of reaction (monitored by TLC). Then water (2 mL) wasadded to reaction mixture and extracted with ethyl acetate(3 mL 2), organic part dried over Na2SO4, ltered and then con-centrated under rotary evaporator and chromatographed oversilica gel by hexane/ethyl acetate (99:1). The obtained disulphides(1b-27b) were characterized and conrmed by comparing the1H NMR and 13C NMR data with those reported in the literature[38-51,108-116]. 2.4.3. Bis(4-methoxyphenyl)disulphide (3b) [45]White solid, mp: 33-36 C (lit [44] 34-35 C), 1H NMR (CDCl3,300 MHz): 7.44 (4H, d, J = 8.77 Hz), 6.88 (4H, d, J = 8.75 Hz), 3.83(6H, s); 13C NMR (CDCl3, 75.4 MHz): 160.3, 133.1, 128.8, 115.0,55.8.
97%	With tert.-butylnitrite; oxygen In 1,2-dichloro-ethane at 50℃; for 1.5h; Sealed tube; Green chemistry;	Typical procedure for disulfides (2a) General procedure: A sealed tube (90 mL) equipped with a magnetic stirring bar and an O2 balloon was charged with dichloroethane (DCE, 20 mL), thiophenol (1a, 4 mmol, 0.44 g) and TBN (0.16 mmol, 4 mol%, 19.2 mL). Then the tube was placed in an oil bath, which was preheated to 50°C. The mixture was stirred for 1 h until starting material was completely consumed as monitored by GC and TLC. After removing the solvent, the residue was purified by column chromatography on silica gel to give the desired diphenyl disulfide (2a, 90%, 0.394 g) as a white solid.
97%	With [bis(acetoxy)iodo]benzene In acetonitrile at 20℃; for 0.5h;	General procedure for the synthesis of disulfide from thiols: General procedure: To a solution of thiols (1m-x) (1.0 mmol) in acetonitrile (2 ml), diacetoxyiodo benzene (DIB) (0.5 mmol) was added. The reaction mixture was stirred for 30 min at room temperature. After completion of the reaction (monitored by TLC), the solvent was evaporated under reduced pressure. The solid obtained was collected, and washed with water. It was dried and recrystallized from ethanol to give disulfides (2m-x).
97%	With Porcine Pancreas Lipase In lithium hydroxide monohydrate at 20℃; for 26h; Green chemistry; Enzymatic reaction;
96%	With sodium perborate In methanol; lithium hydroxide monohydrate for 2h; Ambient temperature;
96.9%	With 2,2′-benzothiazole disulfide In chloroform for 24h; Ambient temperature;
96%	With calcium hypochlorite; Montmorillonite K₁₀ In hexane at 20℃; for 0.25h;
96%	With air In hexane at 30℃; for 2h;
96%	With oxygen In methanol at 40℃; for 3h;
96%	With Co(salophen) In ethanol at 60℃; for 3h;
96%	With manganese dihydrogen carbonate; 3,4,5-trihydroxybenzoic acid; oxygen; anhydrous sodium carbonate In lithium hydroxide monohydrate at 80℃; for 4h; Schlenk technique; Green chemistry;
96%	With sodium methoxide In methanol at 20℃; for 7h; Green chemistry;	A typical procedure for the preparation of symmetrical disulfides General procedure: A variety of thiols (10mmol) were added into sodium methoxide 30 wt. % in methanol(1.85 mL, 10mmol) (NaOMe/MeOH-30), and the solution was stirred at room temperatureunder air atmosphere. After completion of the reaction, the desired products wereextracted with ethyl acetate or n-hexane (3×2mL). The collected extracts were driedover Na2SO4 and concentrated under reduced pressure. The pure symmetrical disulfideswere obtained as liquids or solids. The known and new products were characterized andidentified by melting point, FT-IR, 1HNMR and 13C NMR, and mass analysis.
95%	With copper nitrate - dinitrogen tetroxide adduct In propan-2-one for 0.0166667h; Ambient temperature;
95%	With aluminum(III) oxide; dimethyl sulfoxide at 40℃; for 0.5h;
95%	In dimethyl sulfoxide at 20℃; for 0.5h;
95%	With iodine In ethanol
95%	With iodine; triethylamine In chloroform at 20℃; for 2.5h;
95%	With air; potassium carbonate In acetonitrile at 20℃; for 0.333333h;
95%	With Nitroharnstoff In dichloromethane at 20℃; for 0.466667h; chemoselective reaction;
95%	With potassium bromate; hexaammonium heptamolybdate tetrahydrate In lithium hydroxide monohydrate; acetonitrile at 20℃; for 0.0833333h;	Typical Procedure General procedure: 4-chlorothiophenol (0.145 g, 1 mmol) was added to a heterogeneous mixture of KBrO3 (0.167 g, 1 mmol), (NH4)6Mo7O24·4H2O (0.124 g, 10 mmol%), and CH3CN/H2O (7:3) (5 mL) and the mixture was stirred under a hood for 4 min at ambient atmosphere and room temperature. The progress of the reaction was monitored by TLC (eluent: EtOAc/n-C6H14, 1/13). After completion, CH2Cl2 (20 mL) was added and the reaction mixture was filtered. The filtrate was washed with 5% NaOH, water, and dried over anhydrous MgSO4. Finally, evaporation of the solvent gave the product with sufficient purity formost purposes
95%	With oxygen; 9-mesityl-10-methylacridin-10-ium perchlorate In methanol at 20℃; for 2h; Schlenk technique; Sealed tube; Irradiation; Green chemistry;	General procedure for synthesis of 1,2-bis(4-methoxyphenyl)disulfane 6a. An oven-dried schlenk tube was charged with a magnetic stir-bar, Acr+Mes ClO4- (5.0mol%) and capped with septa. After evacuation under vacuum, a balloon filled withoxygen was connected to the Schlenk tube through the side arm. Then, 4-methoxybenzenethiol 1a (1.0 mmol) and methanol 2a (3.0 mL) were injected in thereaction tube. The reaction mixture was irradiated with visible light (blue lightemitting diodes (LEDs) 3.0 W) with vigorously stirring at room temperature for 2 h.After completion of the reaction, as indicated by TLC, the pure product 6a wasobtained by flash column chromatography on silica gel using petroleum ether andethyl acetate.
94%	With air; trichloro(trifluoromethanesulfonato)titanium(IV); sodium iodide In acetonitrile for 2.3h; Heating;
94%	With hexamethylenetetramine-2Br₂ In dichloromethane; lithium hydroxide monohydrate at 30℃; for 0.133333h;
94%	With N,N′-bis(salicylidene)ethylenediaminocobalt(II) In ethanol at 50℃; for 0.666667h;
94%	With nickel(II) ferrite; dihydrogen peroxide In acetonitrile at 20℃; for 0.0833333h; Green chemistry; chemoselective reaction;
94%	In dimethyl sulfoxide at 95℃; for 6h;
94%	With tris(2-phenylpyridinato-C<SUP>2</SUP>,N)iridium(III) In propan-2-one at 20℃; for 3h; Inert atmosphere; Sealed tube; Irradiation; Green chemistry;
94%	With chloro(4-1,5-cyclooctadiene)(1,3-bis(2,4,6-tris(diphenylmethyl)phenylimidazol-2-ylidene))rhodium(I) In neat (no solvent) at 20℃;
93%	With potassium hydroxide; potassium hexacyanoferrate(III)
93%	With benzyltriphenylphosphonium peroxodisulfate In acetonitrile for 0.9h; Heating;
93%	With 1-butyl-4-aza-1-azoniabicyclo[2.2.2]octane dichromate In acetonitrile for 0.9h; Heating;
93%	With monochloro poly(styrenehydantoin) In lithium hydroxide monohydrate at 20℃; for 6h;
93%	With copper hydroxy phosphate In tetrahydrofuran; lithium hydroxide monohydrate at 20℃; for 2h; Irradiation;
93%	With TiO₂/MoS₂ (10:1 molar ratio of Ti to Mo) nanocomposite; air In ethanol at 20℃; Irradiation; Green chemistry;	General procedure for the synthesis of disulfides General procedure: TiO2/MoS2 (10:1 molar ratio, 10 mg) was added to a solution of thiol 1 (1 mmol) in ethanol (1 mL). The reaction mixture was stirred under a 14W CFL irradiation at a distance of 10 cm at room temperature for a certain time. After reaction (monitored by thin-layer chromatography, TLC), ethyl acetate was added, and the solid catalyst was recovered by centrifugation. The reaction mixture was extracted with ethyl acetate and washed with water. The combined organic phase was then dried over Na2SO4 and concentrated under reduced pressure to give the crude residue, which was purified by column chromatography with petroleum ether-ethyl acetate to afford the pure product 2. The recovered catalyst was then washed with ethanol and deionized water, dried under vacuum, and reused for the next run.
93%	With 2,2'-(((diselanediylbis(2,1-phenylene))bis(azanediyl))bis(methylene))diphenol In acetonitrile at 20℃; for 7h;
93%	With CsPbBr₃ In dichloromethane at 20℃; for 12h; Irradiation; Green chemistry;
93%	With C₄₈H₉₀N₁₂Si₂⁽²⁺⁾*2F₆P^(1-) In [D₃]acetonitrile for 19h; Inert atmosphere; Schlenk technique; Sealed tube;
93%	With sodium hydroxide; potassium hexacyanoferrate(III) In lithium hydroxide monohydrate at 20℃; for 1h; Sealed tube;
92%	With sodium chlorine monoxide In acetonitrile at 20℃; for 0.0833333h;
92%	With tert.-butylhydroperoxide; vanadyl(IV) acetylacetonate In dichloromethane at -15 - 20℃;
92%	With rosolic acid In methanol at 20℃; for 1h;
92%	With magnetic ion exchanged Montmorillonite-k10 In tetrahydrofuran at 50℃; for 1h; Green chemistry;
92%	With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen In ethanol for 0.333333h; Sealed tube; Irradiation; chemoselective reaction;	3.2 Procedure for the oxidation of thiols to disulfides General procedure: 0.6 mmol of thiol 1 and 90 μL (1/3 mol/L) TEMPO/EtOH (and 1.8 mmol of thiol 3) were combined in a 10 mL Pyrex vessel with 1 mL of EtOH dissolved. Subsequently, O2 was injected into the sealed vessel to reach 0.1 MPa of pressure. Then the reaction mixture was magnetically stirred at 1500 rpm and simultaneously illuminated with 3 W blue LEDs until it came to an end monitored by thin layer chromatography (TLC). The reaction pressure was released and the crude products were purified with column chromatograph (petroleum ether: ethyl acetate = 80:1). Then the target product was obtained.
91%	With oxygen In various solvent(s) for 1h; Ambient temperature;
91%	In lithium hydroxide monohydrate; N,N-dimethyl-formamide; acetonitrile for 1h; Ambient temperature; pH=9.0;
91%	With NaNO₂ In lithium hydroxide monohydrate at 20℃; for 0.0666667h;
91%	With CsF-Celite In acetonitrile Reflux;	General procedures for the synthesis of symmetrical disulfides General procedure: CsF-Celite (1.59 g) was stirred in 10 mL of acetonitrile, theappropriate thiol (5 mmol) was then added, and the solutionwas stirred for 5-48 h. The reaction progression was monitoredby TLC. Once the reaction was complete, the mixture wasfiltered, and the filtrate evaporated under reduced pressure.The resultant disulfide was characterized by 1H and 13C andused in thiosulfinate synthesis without further purification.
91%	With titanium(IV) dioxide; oxygen In acetonitrile for 0.416667h; Irradiation;
90%	With bis<benzyltriethylammonium> dichromate In dichloromethane at 0 - 5℃; for 1h;
90%	With dioxochloro(trimethylsiloxy)chromate(VI) In dichloromethane at -10℃; for 0.25h;
90%	With sodium (meta)periodate In lithium hydroxide monohydrate at 20℃; for 0.0333333h;
90%	With 1,4-dichloro-1,4-diazoniabicyclo[2,2,2]octane bischloride In lithium hydroxide monohydrate at 50℃; for 0.3h;
90%	With [Mn(III)(BHBPDI)Cl]; oxygen In ethanol at 20℃; for 5h;
90%	With sodium lauryl sulfate In lithium hydroxide monohydrate at 5℃; for 0.0166667h;
90%	With hexachlorophosphazene at 25℃; for 0.0333333h; Green chemistry;	General Procedure for the Preparation of Disulfides General procedure: A mixture of thiol (1 mmol) and TAPC (0.5 mmol, 0.174 g) was prepared. Themixture was stirred at room temperature for 2 min (Table 2). The progress of the reactionwas monitored by TLC. After the completion of the reaction, H2O (10 mL) was added tothe reaction mixture and filtered to afford pure product. In the case of liquid disulfides, theresidue was then extracted with EtOAc (4 × 5 mL), and the combined extracts were driedover MgSO4. The filtrate was evaporated, and the corresponding disulfide was obtained asthe only product.
90%	With potassium carbonate; copper chloride (II) In methanol
90%	With 4,5,6,7-tetrachloro-2′,4′,5′,7′-tetraiodofluorescein disodium salt; anhydrous sodium carbonate In lithium hydroxide monohydrate at 20℃; for 8h; Irradiation;
90%	With oxygen; 1-n-hexyl-3-methylimidazol-1-ium bromide at 50℃; for 1.16667h; Green chemistry;
90%	With 2',3',4',5'-tetra-O-acetylriboflavin; iodine In <i>tert</i>-butyl alcohol at 26℃; for 8h; Darkness; Green chemistry;	Dioctyl Disulfide (3a): Typical Procedure General procedure: A mixture of octane-1-thiol (2a; 73.1 mg, 0.50 mmol), flavin 1a(13.6 mg, 0.025 mmol), I2 (6.35 mg, 0.025 mmol), and t-BuOH(1.0 mL) was stirred at 26 °C (water bath) for 8 h under air (1atm, balloon) in the dark. The solvent was then evaporated andthe residue was purified by column chromatography (silica gel,CHCl3) to give a colorless oil: yield: 70.7 mg (97%).
89%	With titanosilicate molecular sieve In cyclohexane at 120℃; for 5h; Inert atmosphere;	4 Weigh 30 mg of ETS-10 catalyst into a reaction tube, then add 0.2 mmol of p-methoxythiophenol and 1 mL of cyclohexane.In a nitrogen atmosphere, the reaction was carried out in a heater at 120 °C for 5 h, and after the experiment was completed, centrifugation was performed.The obtained solid phase product was subjected to flash column chromatography (the volume ratio of elution reagent petroleum ether and ethyl acetate was 10:1) to obtain a pale yellow liquid.The yield of the product can reach 89%
88%	With tetramethylammonium chlorochromate In acetonitrile for 1.4h; Heating;
88%	With potassium peroxodisulfate; 1-butyl-3-methyl-1H-imidazol-3-ium bromide at 65 - 70℃; for 0.333333h;
88%	With NiCl₂·6H₂O; cadmium selenide; sodium hydroxide In lithium hydroxide monohydrate at 20℃; for 4h; Irradiation; Inert atmosphere;
88%	With bromine; mesoporous silica In dichloromethane; lithium hydroxide monohydrate at 20℃; for 0.333333h;
87%	With Fe-EDTA; oxygen In methanol; lithium hydroxide monohydrate at 30℃; for 1h; pH = 7.8;
87%	With sodium hydroxide; cobalt phthalocyaninetetrasulphonamide; oxygen In lithium hydroxide monohydrate at 20℃; for 0.5h;
87%	With 1,3-dibromo-5,5-dimethylhydantoin In chloroform at 20℃; for 1h; Inert atmosphere;
87%	With sodium perborate tetrahydrate; glacial acetic acid In lithium hydroxide monohydrate at 4℃;
86%	With (Bu₄N)₂S₂O₈ at 20℃; for 0.0833333h;
86%	With bis(trichloromethyl) carbonate; triethylamine; Triphenylphosphine oxide In chloroform for 6h; Heating;
86%	With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen In toluene at 110℃; for 12h;	6 Two pairs of synthetic steps methoxybenzene disulfide To a reaction flask equipped with 3mL of toluene were added successively 0. 05mmol The TEMPO, lmmol of 4-methoxy thiophenol, substituted with an oxygen atmosphere, the reaction was refluxed for 12 hours, the reaction was complete gussets. Direct mix sample through the column. The product was obtained in 86% yield
85%	With Fe(BTC); oxygen In acetonitrile at 70℃; for 2.5h;

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[91]Li, Xu-Bing; Li, Zhi-Jun; Gao, Yu-Ji; Meng, Qing-Yuan; Yu, Shan; Weiss, Richard G.; Tung, Chen-Ho; Wu, Li-Zhu [Angewandte Chemie - International Edition, 2014, vol. 53, # 8, p. 2085 - 2089][Angew. Chem., 2014, vol. 126, # 8, p. 2117 - 2121,5]
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[99]Current Patent Assignee: ZHENJIANG WEIZE BIOLOG MEDICAL TECHNOLOGY - CN105294371, 2016, A Location in patent: Paragraph 0044; 0045; 0046; 0047; 0097; 0098; 0099; 0100
[100]Dhakshinamoorthy, Amarajothi; Alvaro, Mercedes; Garcia, Hermenegildo [Chemical Communications, 2010, vol. 46, # 35, p. 6476 - 6478]

2
[ 5335-87-5 ]
[ 1153-43-1 ]

Yield	Reaction Conditions	Operation in experiment
93%	With Oxone; potassium bromide In water; acetonitrile at 20℃; for 0.5h;	General procedure for synthesis of thiosulfonates from disulfides: General procedure: oxone(2.0 mmol) was added to a well-stirred solution of MX (KBr, KCl, NaBr andNaCl, 0.5 mmol) in aqueous acetonitrile (50:50, v/v), followed by substrate(1.0 mmol) was added. Resulting mixture was stirred for the appropriateperiod of time (Table 3) at room temperature. After complete consumption ofthe starting material as observed by TLC, water (50 mL) was added and themixture was extracted with ethyl acetate. The extract was washed with brine,dried over anhydrous sodium sulfate and evaporated to afford thecorresponding thiosulfonate as the sole product. It was further recrystallizedusing mixture of ethyl acetate and petroleum ether to remove color impurities.All of the products are known compounds and were characterized bycomparison with authentic samples (NMR spectra and melting points).
89%	With trichloroisocyanuric acid; silica gel at 20℃; grinding; neat (no solvent); chemoselective reaction;
88%	With hydrogenchloride; water In acetonitrile at 20℃; Electrochemical reaction;

85%	With tert.-butylhydroperoxide In dichloromethane at 60℃; for 2h;	3 Example 3 Di-p-methoxyphenyl disulfide (20 mmol, 5.56 g) was sequentially added to a 100 mL single-mouth bottle.70% t-butyl hydroperoxide (80 mmol, 10.29 g) and 40 mL of dichloromethane,The reaction was carried out at 60 ° C for 2 h. After the reaction is(TLC monitoring),Stop heating, cool to room temperature, add 100 mL of water,Extract with dichloromethane (3 x 100 mL), combine the organic layers and dry.Concentrated under reduced pressure,Column chromatography (developing solvent: petroleum ether: ethyl acetate = 20:1) gave white title product.The yield was 85% (5.27 g).
50%	With 1,1,1,3',3',3'-hexafluoro-propanol; water; lithium perchlorate; acetic acid at 20℃; for 8h; Electrochemical reaction; chemoselective reaction;
	With Perbenzoic acid
	With Selectfluor In acetonitrile Ambient temperature;
	With 3-chloro-benzenecarboperoxoic acid
	With dihydrogen peroxide; acetic acid In water at 0 - 20℃; for 50h; Inert atmosphere;

Reference： [1]Natarajan, Palani [Tetrahedron Letters, 2015, vol. 56, # 27, p. 4131 - 4134]
[2]Location in patent: experimental part Xu, Yali; Peng, Yong; Sun, Junhui; Chen, Jiuxi; Ding, Jinchang; Wu, Huayue [Journal of Chemical Research, 2010, # 6, p. 358 - 360]
[3]Strehl, Julia; Hilt, Gerhard [European Journal of Organic Chemistry, 2022, vol. 2022, # 1]
[4]Current Patent Assignee: ZHEJIANG UNIVERSITY OF TECHNOLOGY - CN108484464, 2018, A Location in patent: Paragraph 0032; 0033; 0034
[5]Liu, Shiwen; Chen, Bocheng; Yang, Yi; Yang, Yuhao; Chen, Qianjin; Zeng, Xiaojun; Xu, Bo [Electrochemistry Communications, 2019, vol. 109]
[6]Leandri; Tundo [Annali di Chimica, 1954, vol. 44, p. 264,267,268]
[7]Zupan, Marko; Iskra, Jernej; Stavber, Stojan [Bulletin of the Chemical Society of Japan, 1995, vol. 68, # 6, p. 1655 - 1660]
[8]Clennan, Edward L.; Stensaas, Kristina L. [Journal of Organic Chemistry, 1996, vol. 61, # 22, p. 7911 - 7917]
[9]Yoshida, Suguru; Sugimura, Yasuyuki; Hazama, Yuki; Nishiyama, Yoshitake; Yano, Takahisa; Shimizu, Shigeomi; Hosoya, Takamitsu [Chemical Communications, 2015, vol. 51, # 93, p. 16613 - 16616]

3
[ 98-68-0 ]
[ 5335-87-5 ]

Yield	Reaction Conditions	Operation in experiment
97.1%	With sulfur dioxide; iron(II) sulfate In water; butan-1-ol at 25℃; for 1.88333h;	4 Example 1 General procedure: A method for continuously producing an aryl disulfide compound by using a 4-chlorobenzenesulfonyl chloride as a raw material, and sequentially performing the following steps: (1) 260 ml of methanol (as a solvent) was injected into the tubular reactor 5 (a metering pump 3 was used), so that the tubular reactor 5 was filled with methanol. 0.094 mol of 4-chlorobenzenesulfonyl chloride (about 20 g), 0.0028 mol of FeSO4 (about 0.42 g), and 0.282 mol of water (about 5.08 g) were dissolved in 200 mL of methanol to prepare about 226 mL of a material solution, and the material solution was stored in In the raw material storage tank 1, the temperature of the material solution was 25 °C. The material solution (flow rate is 2 mL/min) is metered by the metering pump 3, and the SO2 gas (flow rate is 52 ml/min) is simultaneously injected into the tubular reactor 5 by the compressor 4, and the reaction temperature is 25 °C. The residence time in the tubular reactor 5 was about 113 min. (2) The storage tank 6 is for collecting the reaction mixture product flowing out from the tubular reactor 5 (mainly by 4,4'-dichlorodiphenyl disulfide as a product, HCl, H2SO4, methanol as a solvent, and Unreacted complete SO2 composition). Remarks: The unreacted SO2 and the generated HCl gas are absorbed by the alkaline liquid in the 8-alkali tank, so that the buffer tank 7 is provided to prevent back suction. (3) taking out the reaction mixture in the storage tank 6, removing the solvent methanol, and treating the reaction mixture by rotary distillation (60 ° C, vacuum degree 0.95 bar) to remove the solvent methanol; adding 30 g of water, filtering, drying the filter cake (drying to constant weight at 40 ° C) gave 13.2 g of 4,4'-dichlorodiphenyl disulfide, and the yield was 97.0%. Note: Traces of water from the reaction mixture are also removed during the above-mentioned rotary steaming process.The H2SO4 in the reaction mixture was dissolved in water and filtered to form a filtrate.
92%	With samarium In N,N-dimethyl-formamide at 60℃; for 0.166667h;
92%	With triphenylphosphine In tetrahydrofuran at 20℃;

72%	With tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide at 20℃; for 20h; chemoselective reaction;
65%	With samarium diiodide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at 60℃; for 0.5h;
63%	With samarium; potassium iodide; nickel dichloride In N,N,N,N,N,N-hexamethylphosphoric triamide at 60℃;
61%	With piperidinium thiotungstate In N,N-dimethyl-formamide for 2.5h; Ambient temperature;
60%	With NaBH₂Se₃ In acetonitrile for 3.5h; Heating;
	With hydrogenchloride; zinc
	With phosphorus; iodine; acetic acid

Reference： [1]Current Patent Assignee: ZHEJIANG UNIVERSITY - CN109836364, 2019, A Location in patent: Paragraph 0040-0051
[2]Liu, Yongjun; Zhang, Yongmin [Tetrahedron Letters, 2003, vol. 44, # 22, p. 4291 - 4294]
[3]Location in patent: scheme or table Kabalka, George W.; Reddy, Marepally Srinivasa; Yao, Min-Liang [Tetrahedron Letters, 2009, vol. 50, # 52, p. 7340 - 7342]
[4]Zheng, Yong; Qing, Feng-Ling; Huang, Yangen; Xu, Xiu-Hua [Advanced Synthesis and Catalysis, 2016, vol. 358, # 21, p. 3477 - 3481]
[5]Guo; Wang; Zhang [Synthetic Communications, 1997, vol. 27, # 1, p. 85 - 88]
[6]Zhan, Zhuangping; Guo, Hongyun; Zhang, Yongmin [Synthetic Communications, 1997, vol. 27, # 16, p. 2749 - 2752]
[7]Dhar, Preeti; Ranjan, Rajeev; Chandrasekaran, Srinivasan [Journal of Organic Chemistry, 1990, vol. 55, # 12, p. 3728 - 3729]
[8]Zhang; Zheng; Cheng; Wang [Organic Preparations and Procedures International, 1996, vol. 28, # 4, p. 467 - 469]
[9]Vinkler; Klivenyi [Acta Chimica Academiae Scientiarum Hungaricae, 1955, vol. 5, p. 159,163]
[10]Kawahara [Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1957, vol. 77, p. 963][Chem.Abstr., 1958, p. 2792]

4
[ 5335-87-5 ]
[ 604-32-0 ]
Benzoic acid (3S,5R,6R,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-6-hydroxy-5-(4-methoxy-phenylsulfanyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1978,vol. 100,p. 7103 - 7106

5
[ 5335-87-5 ]
[ 122-52-1 ]
[ 56806-76-9 ]

Yield	Reaction Conditions	Operation in experiment
80%	With air In acetonitrile at 20℃; for 8h; Green chemistry;	2 Example 2 Synthesis of O, O-Diethyl S-(4-methoxyphenyl) thiophosphate Weigh 0.2 mmol of triethyl phosphite,0.2mmol 1,2-bis(4-methoxyphenyl) disulfide addedAdd a magnetic stir bar and 2 mL of acetonitrile to a 15 mL reaction tube.The reaction was stirred at room temperature for 8 h as shown in the formula (2).After completion of the reaction, the solvent was evaporated with a rotary evaporator, and then extracted with ethyl acetate (10 mL), dried over anhydrous sodium sulfate.Finally, use a rotary evaporator at -0.08 MPa,The organic solvent was distilled off under reduced pressure at 40 ° C to obtain the product O, O-diethyl S-(4-Methoxyphenyl) phosphorothioate in a yield of 80%. O,O-diethyl S-(4-methoxyphenyl) phosphorothioateNuclear magnetic characterization and existing spectral feature structures were confirmed. The characterization data of this compound is as follows: colorless oil.
	With hydroquinone In benzene

Reference： [1]Current Patent Assignee: GUANGDONG UNIVERSITY OF TECHNOLOGY - CN108774260, 2018, A Location in patent: Paragraph 0007; 0032-0034
[2]Harvey,R.G. et al. [Journal of the American Chemical Society, 1963, vol. 85, p. 1618 - 1623]

6
[ 120-72-9 ]
[ 5335-87-5 ]
[ 116757-20-1 ]

Yield	Reaction Conditions	Operation in experiment
97%	With iodine; dimethyl sulfoxide In carbonic acid dimethyl ester at 40℃; for 6h;
96%	With iron(III) trifluoride; iodine In acetonitrile at 80℃; for 36h; regioselective reaction;
80%	With iodine In ethanol at 20℃; for 12h;	Typical experimental procedure for the iodine-promoteddirect 3-selanyl- and 3-sulfenylation of indoles withdichalcogenides General procedure: indole (0.5 mmol), disulfide (0.28 mmol), I2 (0.25 mmol), and EtOH (3 mL) were added to a Schlenk tube or round-bottomed flask and stirred at room temperature for 12 h. After the reaction was finished, the reaction mixture was washed with sodium thiosulfate. Then the mixture was extracted with ethyl acetate.The combined organic extracts were dried over Na2SO4, concentrated under vacuum, and the resulting residue was purified by silica gel column chromatography to afford the desired product. Complete characterization of the products and selected 1Hand 13C NMR spectra for 3, 4, and 5 are presented in the Supplemental Materials (Figures S1-S6)

78%	Stage #1: 4,4'-dimethoxyphenyl disulfide With ammonium peroxydisulfate In methanol at 70℃; for 3h; Stage #2: indole In methanol at 20 - 70℃;
78%	With potassium iodate; glycerol In neat (no solvent) at 100℃; for 6h; Inert atmosphere; Schlenk technique;
75%	With iron(III) chloride; potassium iodide In dimethyl sulfoxide at 60℃; for 8h;	General procedure for preparation FeCl₃/KI mediated chalcogenylation of indoles derivatives General procedure: A mixture of indole 1a-f (1.0 mmol), dichalcogenide 2a-i or 4a-f (0.5 mmol), FeCl3 (10 mol%) and KI (10 mol%) in DMSO (2 mL) was stirred at 60 °C for 3 h until complete consumption of the starting material, as monitored by TLC. After the reaction was finished, the mixture was poured into EtOAc (15 mL) and washed with sat. NaCl soln (3 × 10 mL), followed by extraction of the aqueous layer with EtOAc (5 × 3 mL). The combined organic layer was dried (anhyd Mg2SO4) and concentrated under reduced pressure. The residue was purified by flash column chromatography (hexane-EtOAc) to afford the 3-chalcogenyl indole product.
72%	With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at 20℃; for 1h;
	With sodium hydride 1.) DMF, room temp., 2.) room temp., 1.5 h; Yield given. Multistep reaction;

Reference： [1]Ge, Wenlei; Wei, Yunyang [Green Chemistry, 2012, vol. 14, # 7, p. 2066 - 2070]
[2]Location in patent: experimental part Fang, Xiao-Li; Tang, Ri-Yuan; Zhong, Ping; Li, Jin-Heng [Synthesis, 2009, # 24, p. 4183 - 4189]
[3]Chen, Su-Qin; Wang, Qian-Mei; Xu, Ping-Chuan; Ge, Shao-Peng; Zhong, Ping; Zhang, Xiao-Hong [Phosphorus, Sulfur and Silicon and the Related Elements, 2016, vol. 191, # 1, p. 100 - 103]
[4]Prasad, Ch. Durga; Kumar, Shailesh; Sattar, Moh.; Adhikary, Amit; Kumar, Sangit [Organic and Biomolecular Chemistry, 2013, vol. 11, # 46, p. 8036 - 8040]
[5]Rafique, Jamal; Saba, Sumbal; Franco, Marcelo S.; Bettanin, Luana; Schneider, Alex R.; Silva, Lais T.; Braga, Antonio L. [Chemistry - A European Journal, 2018, vol. 24, # 16, p. 4173 - 4180]
[6]Luz, Eduardo Q.; Seckler, Diego; Araújo, Janylson Souza; Angst, Leonardo; Lima, David B.; Maluf Rios, Elise Ane; Ribeiro, Ronny R.; Rampon, Daniel S. [Tetrahedron, 2019, vol. 75, # 9, p. 1258 - 1266]
[7]Yu, Yuanzu; Zhou, Yan; Song, Zengqiang; Liang, Guang [Organic and Biomolecular Chemistry, 2018, vol. 16, # 27, p. 4958 - 4962]
[8]Atkinson, Joseph G.; Hamel, Pierre; Girard, Yves [Synthesis, 1988, # 6, p. 480 - 481]

7
[ 74-83-9 ]
[ 15015-57-3 ]
[ 5335-87-5 ]

Reference： [1]Journal of Physical Chemistry,1994,vol. 98,p. 4069 - 4075

8
[ 952-92-1 ]
[ 5335-87-5 ]
1-Benzyl-6-(4-methoxy-phenylsulfanyl)-1,4-dihydro-pyridine-3-carboxylic acid amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
28%	In ethanol at 40℃; for 24h; in the dark;

Reference： [1]Fujimori, Ken; Nagata, Toshiyuki; Oae, Shigeru [Tetrahedron Letters, 1983, vol. 24, # 47, p. 5231 - 5232]

9
[ 5335-87-5 ]
[ 696-63-9 ]

Yield	Reaction Conditions	Operation in experiment
99%	With hydrogenchloride; diphenylphosphinopolystyrene In tetrahydrofuran for 6h; Heating;
97%	In tetrahydrofuran at 20℃; for 0.833333h; Green chemistry;	5.Cleavage of Bis-(4-methoxyphenyl) disulfide (Entry 5): To a round bottom flask were charged THPP (23.0mg, 0.11 mmol, 1.10 eq) and the basic buffer solution [tris-(hydroxymethyl)-aminomethane-CaCl2 based buffer; pH 8.00; 1.0 mL]. The reaction mixture was stirred at room temperature for about 5 min and then to this homogenous solution was charged the solution of Bis-(4-methoxyphenyl) disulfide (27.8 mg, 0.10 mmol, 1.00 eq.)in 0.5 mL of THF. This homogeneous aqueous reaction mixture was stirred at room temperature until the reaction completes (about 45 min). After completion of the reaction, the reaction mixture was extracted with a solvent mixture 50% hexane in ethyl acetate (2 X 2mL). The combined organic layer was washed with 10% NaCl solution, separated and dried over anhydrous Na2SO4. The volatiles were evaporated under vacuum at 25-30 °C to yield the free thiol (27.2 mg, 97% yield).
92%	With ammonia; aluminium at 25℃; for 2h;

86%	With pyridine; borane-pyridine complex In lithium hydroxide monohydrate; acetonitrile at 20℃; for 12h; Inert atmosphere; Irradiation;	General procedure: A 4 mL vial was placed under argon. The diaryldisulfide (0.1 mmol, 1 equiv.) was added followed by acetonitrile/H2O 1:1 mixture as a solvent (1 mL) and borane-pyridine complex (0.1 mmol, 8 M in pyridine, 1 equiv.). The reaction was then stirred at room temperature under the irradiation of 440 nm blue LEDs for 12 h. After reaction, the reaction mixture was extracted with Et2O. The solvent was removed under the vacuo and the reside was purified by column chromatography on silica gel (diethyl ether/pentane) to provide the corresponding products.
	With lithium aluminium hydride In tetrahydrofuran at 20℃; for 27h; Inert atmosphere; Reflux;
	With hydrogenchloride; zinc In lithium hydroxide monohydrate Inert atmosphere; Cooling with ice;

Reference： [1]Amos, Richard A.; Fawcett, Shayne M. [Journal of Organic Chemistry, 1984, vol. 49, # 14, p. 2637 - 2639]
[2]McNulty, James; Krishnamoorthy, Venkatesan; Amoroso, Dino; Moser, Michael [Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 19, p. 4114 - 4117]
[3]Sato, Ryu; Akaishi, Ryouichi; Goto, Takehiko; Saito, Minoru [Bulletin of the Chemical Society of Japan, 1987, vol. 60, # 2, p. 773 - 774]
[4]Lee, Sunggi; Park, Changhee [Bulletin of the Korean Chemical Society, 2022]
[5]Coulter, Matthew M.; Kou, Kevin G. M.; Galligan, Baye; Dong, Vy M. [Journal of the American Chemical Society, 2010, vol. 132, # 46, p. 16330 - 16333]
[6]Location in patent: experimental part Xu, Hua-Jian; Liang, Yu-Feng; Cai, Zhen-Ya; Qi, Hong-Xia; Yang, Chun-Yan; Feng, Yi-Si [Journal of Organic Chemistry, 2011, vol. 76, # 7, p. 2296 - 2300]

10
[ 5335-87-5 ]
[ 15015-57-3 ]

Reference： [1]Canadian Journal of Chemistry,1981,vol. 59,p. 2298 - 2302

11
[ 5335-87-5 ]
[ 133670-30-1 ]

Yield	Reaction Conditions	Operation in experiment
74%	With 3-chloro-benzenecarboperoxoic acid In dichloromethane at -78℃; for 3h; Inert atmosphere;	General procedures for the synthesis of symmetric and asymmetricthiosulfinates General procedure: The selected disulfide (3.0 mmol) was dissolved in dry DCM(5 mL) under a N2 atmosphere at -78 °C. m-CPBA (0.52 g, 3.0mmol), dissolved in dry DCM (5 mL), was then slowly addeddropwise. Once the addition was complete, the reaction wasleft to stir for 3 h, slowly warming to 0 °C. The reaction wasquenched with saturated NaHCO3, and the resulting aqueoussolution was extracted 3 times with DCM. The combinedorganic fractions were then dried over anhydrous MgSO4and evaporated under reduced pressure. The crude productwas then purified by silica gel flash column chromatography(n-hexane/ethyl acetate). After purification, all thiosulfinateswere stored at -80 °C until required. All stock solutions wereprepared in DMSO and stored at -20 °C.
	With 3,3-dimethyldioxirane

Reference： [1]Roseblade, Ariane; Ung, Alison; Bebawy, Mary [Acta Pharmacologica Sinica, 2017, vol. 38, # 10, p. 1353 - 1368]
[2]Clennan, Edward L.; Stensaas, Kristina L. [Journal of Organic Chemistry, 1996, vol. 61, # 22, p. 7911 - 7917]

12
[ 5335-87-5 ]
[ 2923-16-2 ]
[ 78914-94-0 ]

Reference： [1]Tetrahedron Letters,1996,vol. 37,p. 9057 - 9058
[2]Chemistry - A European Journal,2015,vol. 21,p. 17220 - 17223

13
[ 624-92-0 ]
[ 5335-87-5 ]
[ 63296-17-3 ]

Yield	Reaction Conditions	Operation in experiment
83%	With N-fluorobis(benzenesulfon)imide In 1,2-dichloro-ethane at 50℃; for 4h; Schlenk technique; Sealed tube;	2. Optimization of the reaction conditions A 25 mL Schlenk tube was charged with bis(4-methoxyphenyl) disulfide 1a (55.7 mg,0.2 mmol), MeSSMe 2a (0.4 mmol) and electrophilic fluorinating reagent (2.5 ~ 20mol%) and solvent (2.0 mL). The tube was sealed and the reaction was then stirredvigorously at 25 ~ 50 C for 4 h. After cooling to room temperature, the reaction mixturewas then concentrated in vacuo, and the crude product was purified by flashchromatography on silica gel to yield the product 3a (isolated yields are based on 0.4mmol of 3).
70%	With N-fluorobis(benzenesulfon)imide In 1,2-dichloro-ethane at 50℃; for 4h;	1 General procedure: The general method for the synthesis of asymmetric disulfide derivatives: add 1,2-dichloroethane (10mL), symmetric disulfide A (1.0mmol), and symmetric disulfide B( 1.0mmol) and NFSI (0.1mmol), the reaction temperature was controlled at 50 degrees Celsius, and the reaction was stirred vigorously for 4 hours. After the completion of the reaction, the reaction solution is concentrated and column chromatography is carried out in sequence to obtain the asymmetric disulfide derivative.
48%	With air; nitric oxide In [D₃]acetonitrile for 1h; Ambient temperature;

48%	With air; nitrogen(II) oxide In [D₃]acetonitrile at 20℃; for 1h;
9 %Spectr.	In acetonitrile at 25℃; for 1h; UV-irradiation; Inert atmosphere;

Reference： [1]Hu, Qingyue; Li, Zheng-Yi; Song, Mengjie; Sun, Xiaoqiang; Yang, Ke [Chinese Chemical Letters, 2022]
[2]Current Patent Assignee: CHANGZHOU UNIVERSITY - CN113563241, 2021, A Location in patent: Paragraph 0018-0025
[3]Itoh, Takashi; Tsutsumi, Nozomi; Ohsawa, Akio [Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 15, p. 2161 - 2166]
[4]Tsutsumi; Itoh; Ohsawa [Chemical and Pharmaceutical Bulletin, 2000, vol. 48, # 10, p. 1524 - 1528]
[5]Deng, Yuchao; Wei, Xiao-Jing; Wang, Hui; Sun, Yuhan; Noël, Timothy; Wang, Xiao [Angewandte Chemie - International Edition, 2017, vol. 56, # 3, p. 832 - 836][Angew. Chem., 2017, vol. 129, p. 850 - 854]

14
[ 696-63-9 ]
[ 87-90-1 ]
[ 5335-87-5 ]
[ 108-80-5 ]

Reference： [1]Synthetic Communications,2001,vol. 31,p. 1825 - 1828

15
[ 5335-87-5 ]
[ 824-79-3 ]
[ 80472-59-9 ]

Yield	Reaction Conditions	Operation in experiment
93.1%	With iodine In dichloromethane at 20℃; for 24h; Inert atmosphere;
93.1%	With iodine In dichloromethane at 20℃; for 24h; Inert atmosphere;	A typical procedure for the synthesis of thiosulfonates from disulfides General procedure: To a mixture of bis(4-(tert-butoxycarbonylamino)phenyl) disulfide (2.21 g, 4.93 mmol,1.0 equiv) and sodium p-toluenesulfinate (2.92 g, 16.4 mmol, 3.3 equiv) suspended in CH2Cl2(88 mL) was added I2 (2.34 g, 9.22 mmol, 1.9 equiv) at room temperature. After stirring for 24 h at the same temperature, to the mixture were added ca. 5% aqueous solution of sodiumbicarbonate (28 mL) and 10% aqueous solution of sodium thiosulfate (35 mL). The mixturewas separated, and then the organic layer was washed two times with ca. 5% aqueoussolution of sodium bicarbonate (55 mL), and then dried (Na2SO4). After filtration, the filtratewas concentrated under reduced pressure. The residue was purified by columnchromatography (Biotage SNAP Ultra 340 g, n-heptane/EtOAc = 90/10 to 80/20) to give S-(4-(tert-butoxycarbonylamino)phenyl) 4-toluenethiosulfonate (2e) (3.37 g, 8.88 mmol,90.1%) as a colorless solid. According to the procedure for preparing S-(4-(tert-butoxycarbonylamino)phenyl) 4-toluenethiosulfonate (2e), S-phenyl 4-toluenethiosulfonate (2b) (4.80 g, 88.6%), S-(4-methoxyphenyl) 4-toluenethiosulfonate (2c) (2.76 g, 93.1%), S-(4-aminophenyl) 4-toluenethiosulfonate (2d) (294 mg, 47.5%), S-(4-chlorophenyl) 4-toluenethiosulfonate (2f)(1.07 g, 70.6%), S-(2-(benzamido)phenyl) 4-toluenethiosulfonate (2g) (2.45 g, 64.6%), and S-(3-thienyl) 4-toluenethiosulfonate (2i) (1.08 g, 81.7%) were prepared from diphenyl disulfide,bis(4-methoxyphenyl) disulfide, bis(4-aminophenyl) disulfide, bis(4-chlorophenyl) disulfide,bis(2-benzamidophenyl) disulfide and bis(3-thienyl) disulfide, respectively.
88%	With iodine In dichloromethane at 20℃; for 3h;

86%	With iodine In dichloromethane for 5h;
74%	With copper(l) iodide; 1,10-Phenanthroline; ammonium tetrafluoroborate In N,N-dimethyl acetamide; water at 30℃; for 18h;
61%	With N-Bromosuccinimide In dichloromethane at 20℃; for 24h;
	With iodine In dichloromethane at 25℃; Inert atmosphere;
	With iodine In dichloromethane at 20℃; for 12h; Inert atmosphere;

Reference： [1]Kanemoto, Kazuya; Sugimura, Yasuyuki; Shimizu, Shigeomi; Yoshida, Suguru; Hosoya, Takamitsu [Chemical Communications, 2017, vol. 53, # 77, p. 10640 - 10643]
[2]Kanemoto, Kazuya; Yoshida, Suguru; Hosoya, Takamitsu [Chemistry Letters, 2018, vol. 47, # 1, p. 85 - 88]
[3]Fujiki, Kiyoko; Tanifuji, Naoki; Sasaki, Yohei; Yokoyama, Taku [Synthesis, 2002, # 3, p. 343 - 348]
[4]Location in patent: experimental part Girijavallabhan, Vinay; Alvarez, Carmen; Njoroge, F. George [Journal of Organic Chemistry, 2011, vol. 76, # 15, p. 6442 - 6446]
[5]Taniguchi, Nobukazu [Journal of Organic Chemistry, 2015, vol. 80, # 3, p. 1764 - 1770]
[6]Kumari, Arram Haritha; Kumar, Jangam Jagadesh; Krishna, Gamidi Rama; Reddy, Raju Jannapu [Synthesis, 2021, vol. 53, # 16, p. 2850 - 2864]
[7]Cai, Wenqiang; Gu, Zhenhua [Organic Letters, 2019, vol. 21, # 9, p. 3204 - 3209]
[8]Zhou, Xin; Peng, Zhiyuan; Wang, Peng George; Liu, Qingchao; Jia, Tiezheng [Organic Letters, 2021, vol. 23, # 3, p. 1054 - 1059]

16
[ 5335-87-5 ]
[ 13214-53-4 ]
2-oxo-imidazolidine-1-carbothioic acid <i>S</i>-(4-methoxy-phenyl) ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	Stage #1: 4,4'-dimethoxyphenyl disulfide With ytterbium; methyl iodide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at 20℃; for 2h; Stage #2: 2-oxoimidazolidine-1-carbonyl chloride In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at 20 - 25℃; for 3h;

Reference： [1]Su, Weike; Gao, Ning; Zhang, Yongmin; Zhu, Junfei [Journal of Chemical Research - Part S, 2002, # 9, p. 442 - 443]

17
[ 629-45-8 ]
[ 5335-87-5 ]
1-butyl-2-(4-methoxyphenyl)disulfide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	In dichloromethane at 25℃; for 1h;
79%	With N-fluorobis(benzenesulfon)imide In 1,2-dichloro-ethane at 50℃; for 4h; Schlenk technique; Sealed tube;	3. General procedure for the scope study General procedure: A 25 mL Schlenk tube was charged with RSSR 1 (0.2 mmol), R1SSR1 2 (0.4 mmol), NFSI (0.02 mmol) and DCE (2.0 mL). The tube was sealed and the reaction was then stirred vigorously at 50 C for 4 h. After cooling to room temperature, the reaction mixture was then concentrated in vacuo, and the crude product was purified by flash chromatography on silica gel to yield the product 3 (isolated yields are based on 0.4 mmol of 3).

Reference： [1]Tanaka, Ken; Ajiki, Kaori [Tetrahedron Letters, 2004, vol. 45, # 29, p. 5677 - 5679]
[2]Hu, Qingyue; Li, Zheng-Yi; Song, Mengjie; Sun, Xiaoqiang; Yang, Ke [Chinese Chemical Letters, 2022]

18
[ 5335-87-5 ]
[ 882-33-7 ]
[ 95914-29-7 ]

Yield	Reaction Conditions	Operation in experiment
84%	With N-fluorobis(benzenesulfon)imide In 1,2-dichloro-ethane at 50℃; for 4h; Schlenk technique; Sealed tube;	General procedure: 25 mL Schlenk tube was charged with RSSR 1 (0.2 mmol), R'SSR' 1' (0.4 mmol), NFSI (0.02 mmol) and DCE (2.0 mL). The tube was sealed and the reaction was then stirred vigorously at 50 C for 4 h. After cooling to room temperature, the reaction mixture was then concentrated in vacuo, and the crude product was purified by flash chromatography on silica gel to yield the product 4 (isolated yields are based on 0.4 mmol of 4).
74%	In dichloromethane at 80℃; for 5h;
54%	In dichloromethane at 20℃; for 12h; Inert atmosphere; Irradiation;

Reference： [1]Hu, Qingyue; Li, Zheng-Yi; Song, Mengjie; Sun, Xiaoqiang; Yang, Ke [Chinese Chemical Letters, 2022]
[2]Tanaka, Ken; Ajiki, Kaori [Tetrahedron Letters, 2004, vol. 45, # 29, p. 5677 - 5679]
[3]Ruan, Hongjie; Meng, Ling-Guo; Zhu, Lingqiong; Wang, Lei [Advanced Synthesis and Catalysis, 2019, vol. 361, # 13, p. 3217 - 3222]

19
[ 998-40-3 ]
[ 5335-87-5 ]
[ 1818-71-9 ]
N⁶-(tri-n-butylphosphoranylidene)=5'-deoxy-5'-[(4-methoxyphenyl)thio]isoguanosine [ No CAS ]

Reference： [1]Journal of the Chinese Chemical Society,2004,vol. 51,p. 1401 - 1406

20
[ 5335-87-5 ]
[ 143-15-7 ]
[ 867017-31-0 ]

Yield	Reaction Conditions	Operation in experiment
98%	With RhCl(PPh₃)3; hydrogen; triethylamine In tetrahydrofuran at 50℃; for 24h;
91%	With hydrogen; triethylamine In tetrahydrofuran at 65℃; for 24h; Inert atmosphere; Green chemistry;	Reactions of disulfides and diselenides with alkyl halides; general procedure General procedure: A 25 mL, three-necked round-bottom flask equipped with a refluxcondenser and a magnetic stir bar was charged sequentially withSiO2-P-RhCl(PPh3)2 (16 mg, 0.006 mmol), disulfide or diselenide(0.2 mmol), alkyl halide (0.44 mmol), THF (1.0 mL), and Et3N(0.2 mL) under argon. Then hydrogen was introduced to the resultingsuspension. The mixture was stirred at 65 °C for 24 h. After beingcooled to room temperature, the mixture was diluted with Et2O (10 mL)and filtered. The SiO2-P-RhCl(PPh3)2 complex was washed withTHF (2 × 5 mL) and Et2O (2 × 5 mL) and reused in the next run. Theether solution was concentrated under a reduced pressure, and theresidue was purified by preparative TLC (hexane) to afford the desiredproduct.

Reference： [1]Ajiki, Kaori; Hirano, Masao; Tanaka, Ken [Organic Letters, 2005, vol. 7, # 19, p. 4193 - 4195]
[2]Zhang, Hean; Hu, Mangen; Cai, Mingzhong [Journal of Chemical Research, 2013, vol. 37, # 10, p. 645 - 647]

21
[ 696-62-8 ]
[ 5335-87-5 ]

Yield	Reaction Conditions	Operation in experiment
96%	With potassium 5-methyl-1,3,4-oxadiazole-2-thiolate; basolite C₃₀₀ In water; N,N-dimethyl-formamide at 130℃; for 24h; Green chemistry;	2.2 Symmetrical Diaryl Disulfides Synthesis; Typical Experimental Procedure General procedure: A mixture of iodobenzene (2.0 mmol), potassium 5-methyl-1,3,4-oxadiazole-2-thiolate (1) (3.0 mmol), MOF-199 (8 mg, 10 % mol) were added to a flask containing 2 mL DMF/H2O (20:1), The reaction continued at 130 °C under atmospheric conditions until completion. Thereaction progress was controlled by thin-layer chromatography. The reaction mixture was then filtered. The filtrate was evaporated under vacuum, CH2Cl2 (20 ml) was addedand the mixture was washed with H2O (2 x 15 ml). Theorganic layer was dried over anhydrous Na2SO4. The solvent was evaporated to give the crude diaryl disulfide, which was purified by plate chromatography (silica gel,n-hexane-ethyl acetate, 20:1). All spectra of the diaryl disulfides are mentioned in the electronic supplementary material.
95%	With 1,10-Phenanthroline; copper(II) choride dihydrate; tetrabutyl ammonium fluoride; caesium carbonate; sulfur In water at 100℃; for 24h; Sealed tube;
95%	With indium(III) oxide; ammonia; water; sulfur In ethanol at 60℃; Green chemistry;	Synthesis of disulfide, 2a-2v; general procedure General procedure: A mixture of alkyl/aryl halide, 1 (1.2 mmol), ammonium hydroxide (1 mmol) and nanosulfur powder (3 mmol, 96 mg) was stirred in 5mL of solvent (ethanol/water (2:1)) at 60 °C. Under this stirring condition indium oxide nanoparticles (3 mol-%) were added to it and the reaction was stirred for a period of 10 min to 1 h at 60 °C. After completion of the reaction as indicated by thin layer chromatography (TLC), the reaction mixture was cooled to room temperature and a 2:1 mixture of ethyl acetate/water (15 mL) was added and indium oxide was removed by centrifuge. The combined organic extracts were dried with anhydrous sodium sulfate and concentrated to give desired product in high purity.

92%	With dmap; nickel(II) chloride hexahydrate; potassium thioacyanate; N,N-dimethyl-formamide at 140℃; for 16h;	4.2 General procedure for synthesis of disulfides General procedure: KSCN (2.2mmol) was added to a magnetically stirred mixture of an aryl halide (2mmol), NiCl2·6H2O (0.6mmol, 30mol%, 0.143g) and DMAP (0.8mmol, 40mol%, 0.098g) in DMF (2mL) at 140°C. The stirring was continued until the starting halide was completely consumed. Next, the reaction mixture was diluted with water (1mL) and extracted with 1:1 EtOAc/hexane (4×2mL). The organic extracts were combined, concentrated and purified by chromatography on silica gel. The desired disulfides were produced in 79-92% yields
91%	Stage #1: para-iodoanisole With isopropylmagnesium chloride In tetrahydrofuran at -78 - -20℃; Inert atmosphere; Stage #2: With disulfur dichloride In tetrahydrofuran at 20℃; Inert atmosphere;	3 Example 3. Synthesis of p-Methoxydiphenyl Disulfide Into a pre-dried reaction flask filled with nitrogen (or argon),Add 100mL of tetrahydrofuran,Cool the mixture to -78°C,Then add p-methoxy iodobenzene (0.1mol),Then slowly add isopropyl magnesium chloride (0.11 mol) dropwise to the reaction solution,The reaction solution is stirred at -78-20,And use gas chromatography to monitor the progress of the reaction,The halogen-magnesium exchange reaction ends after about 30-90 minutes.Then add to the reaction systemDichlorodisulfide (0.05mol),And slowly warm the reaction solution to room temperature,Quench the reaction with saturated ammonium chloride solution,Extract the organic phase with ether or ethyl acetate,Dry the organic phase with anhydrous magnesium sulfate,Concentrate the organic phase to obtain 12.7 g of light yellow solid p-methoxydiphenyl disulfide,The yield is 91%, and the purity is ≥95%.
90%	Stage #1: para-iodoanisole With potassium 5-methyl-1,3,4-oxadiazole-2-thiolate In N,N-dimethyl-formamide at 20℃; for 0.333333h; Stage #2: With copper(l) chloride In N,N-dimethyl-formamide at 130℃; for 5h;	Symmetrical organic disulfides synthesis; typical experimental procedure General procedure: A mixture of iodobenzene (2.0 mmol), potassium 5-methyl-1,3,4-oxadiazole-2-thiolate(2) (3.0 mmol), and DMF (4 mL) was stirred at room temperature for 20 min until the potassium salt had completely dissolved. CuCl (0.6 mmol, 61 mg) was then added to the solution and stirring was continued at 130 °C for the appropriate time (Table 3) under air. After completion of the reaction, the DMF was evaporated, CH2Cl2 (15 mL) was added, and the mixture washed with H2O (3 × 10 mL). The organic layer was dried over anhydrous Na2SO4. The solvent was evaporated in vacuo to give diphenyl disulfide which was purified by preparative TLC (silica gel, eluent n-hexane: EtOAc = 50:1).Selected spectral data for representative disulfides: 6d (Table 3, entry 4): mp = 41-43 C (42-43 C lit.5j,k); 1H NMR (CDCl3, 400 MHz): d 3.82 (s, 6H),6.87 (d, J = 8.8 Hz, 4H), 7.32 (d, J = 8.8 Hz, 4H); 13C NMR (CDCl3, 100 MHz): d 55.4, 114.7, 127.4, 132.8, 159.0 ppm
90%	With morpholinium morpholine-1-carbodithioate; copper(l) chloride; potassium hydroxide In water; N,N-dimethyl-formamide at 110℃; for 20h; Green chemistry;	4.2. General procedures for the synthesis of diaryl (dialkyl) disulfides derivatives General procedure: To a stirred mixture of aryl (alkyl) halide (2.0 mmol), morpholin-4-ium morpholine-4-carbodithioate(0.75 g, 3.0 mmol) in DMF/H2O (2:1) was added CuCl (0.3 g, 3.0 mmol) followed byKOH (2.0 g) and heated at 110°C under atmospheric conditions until completion (20 h). Theprogress of the reaction was monitored by TLC. Upon completion of the reaction, the mixturewas cooled to room temperature and then filtered. The filtrate was evaporated under vacuum,CH2Cl2 (20 ml) was added and the mixture was washed with H2O (2 × 15 ml). The combinedorganic layer was dried over Na2SO4, and filtered to afford the crude diaryl (dialkyl) disulfide,which was purified by plate chromatography (silica gel, n-hexane: ethyl acetate, 20:1; in the caseof 3i and 3k was 4:1).
90%	With copper(l) iodide; water; oxygen; sodium hydrogencarbonate; thiourea at 115 - 120℃; for 14h; Green chemistry;	2.4. General procedure for conversion of aryl halides to disulfides inPEG General procedure: In a round-bottom flask (25 mL) equipped with a condenser,Europhtal (8020) catalyst solution (0.07 mL) was added to amixture of an aryl halide (2.0 mmol), thiourea (2.2 mmol), H2O(0.1 mL), CuI (20 mol%, 0.076 g) and NaHCO3 (3.0 mmol) in PEG 200(1 mL). The mixture was stirred magnetically in an oil bath at115-120 °C. After consumption of aryl halide, the mixture wasdiluted withwater (0.5 mL) and extracted with 1:2 n-hexane/EtOAc(3 x 1 mL). The organic layers were decanted, combined, andconcentrated to yield the crude product, whichwas further purifiedby silica gel chromatography, using n-hexane as eluent to providethe pure desired disulfide.
88%	With copper(l) iodide; hexachloroethane; sodium carbonate; thiourea In water at 120℃; for 14h;
88%	With 1,10-Phenanthroline; potassium sulfide; iron oxide; potassium hydroxide In N,N-dimethyl-formamide at 120℃; for 20h; Inert atmosphere; Green chemistry;	Symmetrical organic disulfides synthesis; typical experimental procedure General procedure: A mixture of aryl iodide (1.0 mmol), K2S(1.0 mmol), Fe3O4 nanoparticle (6 mg), 1,10-Phenanthroline (6 mg) and KOH(0.05 g) were added to a flask containing 2 mL DMF. Thereaction continued at 120 °C under N2atmospheric conditionsuntil completion.The reaction progress was controlledby thin-layer chromatography. The reaction mixture wasthen filtered. The filtrate was evaporated under vacuum;afterward, CH2Cl2(20 mL) was added and the mixture waswashed with H2O(2 × 15 mL). The organic layer was driedover anhydrous Na2SO4.The solvent was evaporated to givethe crude diaryl disulfide, which was purified by plate chromatography(silica gel, n-hexane-ethyl acetate, 20:1). (Fordetails, please see Electronic Supplementary Information.)
84%	With sulfur; potassium hydroxide In water at 130℃; for 24h; Green chemistry;
78%	With basolite C₃₀₀; thiourea; potassium hydroxide In water at 130℃; for 20h;	Symmetrical diaryl disulfides synthesis: general experimental procedure General procedure: The prepared catalyst (4 mg) was added to a mixture of aryl halide (1.0 mmol), thiourea (0.228 g, 3.0 mmol) KOH (0.168 g, 3.0 mmol) in 2 ml PEG/H2O (20:1) at 130°C under atmospheric conditions until completion (20 h). The progress of the reaction was monitored by TLC. After removal of solvent, the residue was purified by chromatography (SiO2; hexane/AcOEt 20: 1) to give the crude diaryl disulfides.
77%	With carbon disulfide; cycl-isopropylidene malonate; triethylamine; copper(l) chloride In N,N-dimethyl-formamide at 100℃; for 4h; Inert atmosphere;	Conversion of aryl iodides into diaryl disulfides using Meldrum’s acid dithioate General procedure: A mixture of Meldrum’s acid (1 mmol) and Et3N (2 mmol) in DMF was stirred for 15 min at r.t. Then, CS2 (1 mmol) was added and stirred for 15 min. Then, the obtained mixture was added to a stirred solution of aryl halide (1 mmol) and CuCl (0.1 mmol) in DMF (2 ml), and heated at 100 C for 4h. When the reaction was completed (TLC), the mixture was extracted with CH2Cl2 (3 3ml) and H2O (3ml). The organic layer was separated and dried (Na2SO4) and the solvent was evaporated in vacuo to give the diaryl disulfide. The product was purified by column chromatography on silica gel (EtOAc / Petroleum ether, 1:4).
72%	With [2,2]bipyridinyl; copper(l) iodide; sulfur In N,N-dimethyl-formamide at 110℃; for 65h;
72%	With [2,2]bipyridinyl; copper(l) iodide; sodium carbonate; sulfur; aluminium In N,N-dimethyl-formamide at 110℃; for 65h; Inert atmosphere;	6 4.3.4 _{RRN No.57,59,61,63}Typical procedure for copper-catalyzed disulfidation of aryl iodides (Table 3) General procedure: To a mixture of sulfur (10.6 mg, 0.3 mmol), CuI (8.5 mg, 0.045 mmol), aluminum powder (53150 m) (16.2 mg, 0.6 mmol), Na2CO3 (15.9 mg, 0.15 mmol), bpy (7.0 mg, 0.045 mmol), and 2-iodotoluene 1a (65.4 mg, 0.3 mmol), DMF (0.5 mL) was added, and the mixture was stirred at 110 °C for 24 h. After the reaction mixture was diluted with Et2O, the solution was washed with H2O and saturated sodium chloride and dried over anhydrous magnesium sulfate. Chromatography on silica gel (hexane) gave di(2-methylphenyl) disulfide (34.0 mg, 92%).
69%	With potassium sulfide; nickel(II) chloride hexahydrate; acetylacetone; potassium hydroxide In water; N,N-dimethyl-formamide at 110℃; for 24h;	General procedure for the synthesis of diaryl(dialkyl) disulfides General procedure: To a stirred mixture of aryl (primary alkyl) halide (2.0 mmol), 0.33 g potassium sulfide (3.0 mmol) and acac (20 mol%) in 2 cm3 DMF (containing a few drops water),NiCl2.6H2O (10 mol%) and then 1.0 g KOH (18.0 mmol) were added and the whole reaction mixture was heated at 110 °C under atmospheric conditions until completion. The progress of the reaction was monitored by TLC. Upon completion of the reaction, the mixture was cooled to room temperature. Then, the pH of mixture was adjusted to 7 with 5 % HCl and filtered. The filtrate was evaporated under vacuum, 20 cm3 ethyl acetate was added and the mixture was washed with H2O (2 x 15 cm3). The combined organic layer was dried over Na2SO4 and filtered to afford the crude diaryldisulfide and dialkyldisulfide, which was purified by preparative chromatography (silica gel, n-hexane:ethyl acetate 20:1; in the case of Table 3, entries 12-15 was 4:1).
67%	With potassium fluoride on basic alumina; thioacetamide; copper(l) chloride In N,N-dimethyl-formamide at 110℃; for 5h;
66%	With copper(II) oxide; sulfur; potassium hydroxide In dimethyl sulfoxide at 80℃; for 0.116667h; Sealed tube; Microwave irradiation;	General procedure for the microwave-assisted synthesis of diorganoyl diselenides, ditellurides and disulfides General procedure: Elemental chalcogen (Se, Te or S, 1.0 mmol), CuO nanopowder (5.0 mol%), KOH (2.0 equiv.), organoyl iodide (0.5 mmol) and DMSO (1 mL) were placed in a specific microwave tube equipped with a magnetic stir bar. The tube was placed in the microwave cavity and submitted to irradiation for 7 or 15 min (see Tables 3 and 4) at 80 ◦C using a maximum power of 100 W. After cooled the reaction system at room temperature the crude product was directly purified by flash column chromatography without previous workup. For example in case of diphenyl diselenide 2a, 20 g of silica gel (230-400 mesh) was used to packing the column and the reaction mixture was directly added to the top of column and eluted with nhexane. Alternatively, the flash chromatograph can be performed by a Super flash purification column SF25-40g with a BSR pump system and eluted with hexane. Flash chromatography was performed by mixing of the crude with silica gel 60 (230-400 mesh) in a proportion of 1:4 using a SimpliFlash with BSR pump system. The identity and purity of the products was confirmed by 1H NMR, 13C NMR, GC/MS and the melting points and all of the spectral data were in perfect agreement with those reported in the literature [14-16,21,27-29,31,47,60].
55%	With potassium 5-methyl-1,3,4-oxadiazole-2-thiolate; nickel(II) chloride hexahydrate; ethylene glycol; potassium hydroxide In water; N,N-dimethyl-formamide at 130℃; for 24h;	Symmetrical Organic Disulfide Synthesis; Typical ExperimentalProcedure General procedure: A mixture of iodobenzene (2.0 mmol), potassium 5-methyl-1,3,4-oxadiazole-2-thiolate (1, 0.462 g, 3.0 mmol), NiCl2·6H2O (10 mol%) and KOH (1.0 g, 18 mmol) were added to a flask containing DMF-H2O (2 mL, 20:1) and EG (0.11 mL, 2 mmol). The reaction mixture was heated at 130 °C under atmospheric conditions until completion, monitored by TLC. The reaction mixture was then filtered, the filtrate was evaporated under reduced pressure, CH2Cl2 (20 mL) was added, and the mixture was washed with H2O (2 × 15 mL). The organic layer was dried over anhydrous Na2SO4, filtered, and the solvent was evaporated to give the crude diaryl/alkyl disulfide, which was purified by preparative TLC (silica gel; n-hexane-EtOAc, 20:1).
51%	With nickel(II) chloride hexahydrate; morpholinium morpholine-1-carbodithioate; potassium hydroxide In water; ethylene glycol; N,N-dimethyl-formamide at 130℃;
	With copper(l) iodide; tetra(n-butyl)ammonium hydroxide; sulfur In water at 40℃; for 24h; Inert atmosphere; Sealed tube; chemoselective reaction;
	With copper(l) iodide; sodiumsulfide nonahydrate; sulfur In N,N-dimethyl-formamide at 110℃; for 15h; Inert atmosphere;
	With sulfur; copper(l) iodide; lithium hydroxide monohydrate In N,N-dimethyl-formamide at 100℃; for 168h; Inert atmosphere;
	Multi-step reaction with 2 steps 1: sodium thiosulfate; copper(l) iodide; N,N`-dimethylethylenediamine / dimethyl sulfoxide / 4 - 12 h / 80 °C 2: dihydrogen peroxide; choline chloride; toluene-4-sulfonic acid / water / 6 h / 60 °C
	With carbon disulfide; potassium cyanide; copper(l) iodide In N,N-dimethyl-formamide at 120℃; for 0.25h;

Reference： [1]Soleiman-Beigi, Mohammad; Mohammadi, Fariba [Catalysis Letters, 2016, vol. 146, # 8, p. 1497 - 1504]
[2]Li, Zhengkai; Ke, Fang; Deng, Hang; Xu, Hualong; Xiang, Haifeng; Zhou, Xiangge [Organic and Biomolecular Chemistry, 2013, vol. 11, # 18, p. 2943 - 2946]
[3]Devi, Namita; Hazarika, Sukanya; Gogoi, Prasanta; Barman, Pranjit [Synthetic Communications, 2018, vol. 48, # 15, p. 1927 - 1938]
[4]Abbasi, Mohammad; Nowrouzi, Najmeh; Latifi, Hadis [Journal of Organometallic Chemistry, 2016, vol. 822, p. 112 - 117]
[5]Current Patent Assignee: WUHAN INSTITUTE OF TECHNOLOGY - CN111763163, 2020, A Location in patent: Paragraph 0051; 0052; 0053; 0054; 0055; 0056; 0057
[6]Soleiman-Beigi, Mohammad; Mohammadi, Fariba [Tetrahedron Letters, 2012, vol. 53, # 52, p. 7028 - 7030]
[7]Soleiman-Beigi, Mohammad; Arzehgar, Zeinab [Journal of Sulfur Chemistry, 2015, vol. 36, # 4, p. 395 - 402]
[8]Abbasi, Mohammad; Sabet, Askar; Sabet, Askar [Journal of Organometallic Chemistry, 2017, vol. 833, p. 10 - 17]
[9]Nowrouzi, Najmeh; Abbasi, Mohammad; Latifi, Hadis [Applied Organometallic Chemistry, 2017, vol. 31, # 3]
[10]Soleiman-Beigi, Mohammad; Mohammadi, Keivan; Mohammadi, Fariba [Journal of the Iranian Chemical Society, 2018, vol. 15, # 7, p. 1545 - 1550]
[11]Soleiman-Beigi, Mohammad; Yavari, Issa; Sadeghizadeh, Fatemeh [RSC Advances, 2015, vol. 5, # 106, p. 87564 - 87570]
[12]Soleiman-Beigi, Mohammad; Sadeghizadeh, Fatemeh; Basereh, Ali [Journal of Sulfur Chemistry, 2017, vol. 38, # 5, p. 572 - 583]
[13]Habibi, Azizollah; Baghersad, Mohammad Hadi; Bilabary, Mina; Valizadeh, Yousef [Tetrahedron Letters, 2016, vol. 57, # 5, p. 559 - 562]
[14]Taniguchi, Nobukazu [Synlett, 2005, # 11, p. 1687 - 1690]
[15]Taniguchi, Nobukazu [Tetrahedron, 2012, vol. 68, # 51, p. 10510 - 10515,6]
[16]Soleiman-Beigi, Mohammad; Arzehgar, Zeinab [Monatshefte fur Chemie, 2016, vol. 147, # 10, p. 1759 - 1763]
[17]Soleiman-Beigi, Mohammad; Hemmati, Maryam [Applied Organometallic Chemistry, 2013, vol. 27, # 12, p. 734 - 736]
[18]Botteselle, Giancarlo V.; Godoi, Marcelo; Galetto, Fabio Z.; Bettanin, Luana; Singh, Devender; Rodrigues, Oscar E.D.; Braga, Antonio L. [Journal of Molecular Catalysis A: Chemical, 2012, vol. 365, p. 186 - 193]
[19]Soleiman-Beigi, Mohammad; Mohammadi, Fariba [Synlett, 2015, vol. 26, # 7, p. 911 - 914]
[20]Soleiman-Beigi, Mohammad; Arzehgar, Zeinab [Heteroatom Chemistry, 2015, vol. 26, # 5, p. 355 - 360]
[21]Xu, Hua-Jian; Liang, Yu-Feng; Cai, Zhen-Ya; Qi, Hong-Xia; Yang, Chun-Yan; Feng, Yi-Si [Journal of Organic Chemistry, 2011, vol. 76, # 7, p. 2296 - 2300]
[22]Location in patent: experimental part Li, Yaming; Nie, Caiping; Wang, Huifeng; Li, Xiaoying; Verpoort, Francis; Duan, Chunying [European Journal of Organic Chemistry, 2011, # 36, p. 7331 - 7338]
[23]Chen, Hsing-Ying; Peng, Wei-Te; Lee, Ying-Hsien; Chang, Yu-Lun; Chen, Yen-Jen; Lai, Yi-Chun; Jheng, Nai-Yuan; Chen, Hsuan-Ying [Organometallics, 2013, vol. 32, # 19, p. 5514 - 5522]
[24]Zhou, Yongsheng [Journal of Chemical Research, 2015, vol. 39, # 6, p. 332 - 335]
[25]Shaikhi Shahidzadeh, Elham; Nowrouzi, Najmeh; Abbasi, Mohammad [Applied Organometallic Chemistry, 2019, vol. 33, # 11]

22
[ 29684-56-8 ]
[ 696-63-9 ]
triethylammonium methylcarboxysulfaminate [ No CAS ]
[ 5335-87-5 ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 4989 - 4992

23
[ 402-67-5 ]
[ 5335-87-5 ]
[ 37692-06-1 ]

Yield	Reaction Conditions	Operation in experiment
86%	With hydridotetakis(triphenylphosphine)rhodium(I); o-phenylenebis(diphenylphosphine); triphenylphosphine In chlorobenzene for 6h; Reflux;

Reference： [1]Arisawa, Mieko; Suzuki, Takaaki; Ishikawa, Tomofumi; Yamaguchi, Masahiko [Journal of the American Chemical Society, 2008, vol. 130, # 37, p. 12214 - 12215]

24
[ 345-83-5 ]
[ 5335-87-5 ]
[ 200959-42-8 ]

Yield	Reaction Conditions	Operation in experiment
87%	With hydridotetakis(triphenylphosphine)rhodium(I); o-phenylenebis(diphenylphosphine); triphenylphosphine In chlorobenzene Reflux;
86%	With bis(1,5-cyclooctadiene)diiridium(I) dichloride; tributylphosphine; o-phenylenebis(diphenylphosphine); caesium carbonate In 1,4-dioxane for 20h; Schlenk technique; Sealed tube; Inert atmosphere; Reflux;	2. General procedure for the thiolation of fluorobenzene (1a) and disulfides (2a). General procedure: Into a 50 mL Schlenk tube, [Ir(COD)Cl]2(0.0034 g, 0.005 mmol) and Cs2CO3 (0.2443 g, 0.75 mmol) were added before the tubewas sealed. Then the reaction tube was evacuated and refilled with nitrogen for threetimes. Then, a solution of dppBz (0.0045 g, 0.01 mmol) and nBu3P (0.0505 g, 0.25 mmol)in dioxane (1 mL) was added in it under a nitrogen flow. The mixture was stirred for halfan hour at room temperature. Subsequently, 4-fluorophenylacetonitrile (1e, 0.0908 g, 0.75mmol) and disulphide (2a, 0.0695 g, 0.25 mmol) dissolved in dioxane (1 mL) were addedinto the tube. The reaction mixture was stirred at the reflux under an atmosphere ofnitrogen for 20 hours and then cooled to room temperature. Upon completion, thereaction mixture was concentrated under reduced pressure. The residue was then purifiedby column chromatography on silica gel using petroleum ether and ethyl acetate as eluentto provide the corresponding product 3e as white crystal in a 88% yield (0.1064 g, 88%).

Reference： [1]Arisawa, Mieko; Suzuki, Takaaki; Ishikawa, Tomofumi; Yamaguchi, Masahiko [Journal of the American Chemical Society, 2008, vol. 130, # 37, p. 12214 - 12215]
[2]Li, Liang; Miao, Hongyan; Ding, Yuqiang [Tetrahedron Letters, 2015, vol. 56, # 46, p. 6405 - 6408]

25
[ 5335-87-5 ]
[ 1493-27-2 ]
[ 3169-69-5 ]

Yield	Reaction Conditions	Operation in experiment
95%	With carbonylhydridotris(triphenylphosphine)iridium(I); tributylphosphine; o-phenylenebis(diphenylphosphine) In chlorobenzene at 130℃; for 20h; Schlenk technique; Sealed tube; Inert atmosphere;	2. General procedure for the thiolation of fluorobenzene (1a) and disulfides (2a). General procedure: Into a 50 mL Schlenk tube, IrH(CO)(PPh3)3 (0.0050 g, 0.005 mmol) was added beforethe tube was sealed. Then the reaction tube was evacuated and refilled with nitrogen forthree times. Then, a solution of dppBz (0.0045 g, 0.01 mmol) and nBu3P (0.0505 g, 0.25mmol) in dioxane (1 mL) was added in it under a nitrogen flow. The mixture was stirredfor half an hour at room temperature. Subsequently, fluorobenzene (1a, 0.0846 g, 0.60mmol) and disulphide (2a, 0.0695 g, 0.25 mmol) dissolved in dioxane (1 mL) were addedinto the tube. The reaction mixture was stirred at reflux under an atmosphere of nitrogenfor 20 hours and then cooled to room temperature. Upon completion, the reaction mixturewas concentrated under reduced pressure. The residue was then purified by columnchromatography on silica gel using petroleum ether and ethyl acetate as eluent to providethe corresponding product 3c as yellow crystal (0.1113 g, 85%).
93%	With hydridotetakis(triphenylphosphine)rhodium(I); o-phenylenebis(diphenylphosphine); triphenylphosphine In chlorobenzene for 6h; Reflux;

Reference： [1]Li, Liang; Miao, Hongyan; Ding, Yuqiang [Tetrahedron Letters, 2015, vol. 56, # 46, p. 6405 - 6408]
[2]Arisawa, Mieko; Suzuki, Takaaki; Ishikawa, Tomofumi; Yamaguchi, Masahiko [Journal of the American Chemical Society, 2008, vol. 130, # 37, p. 12214 - 12215]

26
[ 97239-80-0 ]
[ 69861-71-8 ]
[ 5335-87-5 ]
[ 1154043-13-6 ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 7858 - 7868

27
[ 5335-87-5 ]
[ 5857-42-1 ]

Reference： [1]Tetrahedron Letters,2009,vol. 50,p. 6231 - 6232
[2]Synthesis,2012,vol. 2012,p. 316 - 322

28
[ 5335-87-5 ]
[ 98-68-0 ]

Yield	Reaction Conditions	Operation in experiment
96%	With dihydrogen peroxide; zirconium(IV) chloride In water; acetonitrile at 25℃; for 0.0166667h;
95%	With dihydrogen peroxide; trichlorophosphate In water at 25℃; for 0.5h; Micellar solution;
92%	With 1,3-dichloro-5,5-dimethylhydantoin; acetic acid In dichloromethane; water at 0 - 20℃; Inert atmosphere;

88%	With N-chloro-succinimide In water; acetonitrile at 20℃; for 2.3h;	Representative experimental procedure to prepare sulfonylchloride from disulfides General procedure: To a stirred solution of p-tolyl disulfide ( 1b) (246.3mg, 1.0mmol) in acetonitrile (2.0mL) and water (0.2mL), N-chlorosuccinimide (802mg, 6.0mmol) was added, and the resulting mixture was stirred at room temperature for 3h. Water (10mL) was added and the resulting mixture was extracted with ethyl acetate (20mL×3). The extract was washed with brine, dried over anhydrous magnesium sulfate, and evaporated. Chromatography on silica gel using n-hexane/ethyl acetate as the eluent gave the sulfonyl chloride ( 4b) (304.7mg, 83%) as colorless crystals.
84%	With sodium hypochlorite pentahydrate; acetic acid at 20℃; for 0.5h;	Representative procedure for the synthesis of sulfonyl chlorides from the reaction of NaOCl•5H₂O with disulfides: General procedure: To a solution of di-p-tolyldisulfide (739.2 mg, 3.0mmol) in acetic acid (11 mL), NaOCl•5H2O (2.47 g, 15.0mmol) was added and stirred at room temperature for 65min. Saturated aqueous sodium thiosulfate (4 mL) and dichloromethane (15 mL) was added to the reaction mixture. The organic layer was separated and the aqueous phase was extracted with dichloromethane (15mL x 2). The combined extracts were dried over anhydrous sodium sulfate, and evaporated to afford p-toluenesulfonyl chloride (915.0 mg, 80%) as colorless crystals. This product is pure enough without further purifications, and is consistent with the commercial reagent.
84%	With sodium hypochlorite pentahydrate; acetic acid at 25℃; for 0.5h;	13 General procedure: 0.7392 g (3.0 mmol) of di-p-tolyl disulfide was dissolved in 11 mL of acetic acid and 2.4681 g (15.0 mmol) of powdered sodium hypochlorite pentahydrate was stirred while stirring at room temperature (25 ° C.) Was added, and after completion of the addition, the mixture was reacted with stirring for 65 minutes. After completion of the reaction, 10 mL of water was added to the obtained reaction mixture to dissolve the solid in the reaction mixture, then extracted with 20 mL of dichloromethane, dichloromethane and acetic acid were distilled off from the extraction solution obtained using a rotary evaporator under reduced pressure The acetic acid which was not removed at this time was removed by azeotropic distillation with hexane to obtain 0.9150 g (4.8 mmol, yield 80%) of p-toluenesulfonyl chloride as a reaction product.
82%	With Oxone; potassium chloride In water at 20℃; for 0.166667h;
	With 1,3-dichloro-5,5-dimethylhydantoin; water; benzyltrimethylammonium chloride In acetonitrile at 0℃; for 0.5h;

Reference： [1]Location in patent: experimental part Bahrami, Kiumars; Khodaei, Mohammad Mehdi; Soheilizad, Mehdi [Synlett, 2009, # 17, p. 2773 - 2776]
[2]Location in patent: experimental part Bahrami, Kiumars; Khodaei, Mohammad M.; Abbasi, Jamshid [Synthesis, 2012, vol. 2012, # 2, p. 316 - 322]
[3]Pu, Yu-Ming; Christesen, Alan; Ku, Yi-Yin [Tetrahedron Letters, 2010, vol. 51, # 2, p. 418 - 421]
[4]Kirihara, Masayuki; Naito, Sayuri; Nishimura, Yuki; Ishizuka, Yuki; Iwai, Toshiaki; Takeuchi, Haruka; Ogata, Tomomi; Hanai, Honoka; Kinoshita, Yukari; Kishida, Mari; Yamazaki, Kento; Noguchi, Takuya; Yamashoji, Shiro [Tetrahedron, 2014, vol. 70, # 14, p. 2464 - 2471]
[5]Okada, Tomohide; Matsumuro, Hiroaki; Iwai, Toshiaki; Kitagawa, Saori; Yamazaki, Kento; Akiyama, Tomomi; Asawa, Tomotake; Sugiyama, Yukihiro; Kimura, Yoshikazu; Kirihara, Masayuki [Chemistry Letters, 2015, vol. 44, # 2, p. 185 - 187]
[6]Current Patent Assignee: NIPPON LIGHT METAL HOLDINGS COMPANY, LTD. - JP2015/74609, 2015, A Location in patent: Paragraph 0031; 0033
[7]Madabhushi, Sridhar; Jillella, Raveendra; Sriramoju, Vinodkumar; Singh, Rajpal [Green Chemistry, 2014, vol. 16, # 6, p. 3125 - 3131]
[8]Location in patent: experimental part Veisi, Hojat [Bulletin of the Korean Chemical Society, 2012, vol. 33, # 2, p. 383 - 386]

29
[ 5335-87-5 ]
[ 368-91-2 ]

Yield	Reaction Conditions	Operation in experiment
77%	With water; Selectfluor In acetonitrile for 1h; Reflux;	A representative experimental procedure to prepare sulfonyl fluorides from disulfides General procedure: To a stirred solution of p-tolyl disulfide (246.3 mg, 1.0 mmol) in acetonitrile (10.0 ml) and water (1.0 ml) was added Selectfluor (2306.2 mg, 6.5 mmol) and the resulting mixture was heated under reflux for 1.5 h. The reaction was monitored by thin layer chromatography (TLC). After the disulfide and the corresponding thiosulfonate disappeared from the TLC, water (10 ml) was added and the resulting mixture was extracted with ethyl acetate (20 ml × 3). The extract was washed with brine, dried over anhydrous magnesium sulfate, and evaporated. Chromatography on silica gel gave the sulfonyl fluoride (299.0 mg, 86%) as colorless crystals.
77%	With Selectfluor In water; acetonitrile at 20℃; for 1h; Reflux;	Representative experimental procedure to prepare sulfonylfluorides from disulfides General procedure: To a stirred solution of p-tolyl disulfide ( 1b) (246.3mg, 1.0mmol) in acetonitrile (10.0mL) and water (1.0mL), Selectfluor (2306mg, 6.5mmol) was added at room temperature for over 20min, and the resulting mixture was heated under reflux. The reaction was monitored via TLC. After the disulfide and the corresponding thiosulfonate disappeared from the TLC, water (10mL) was added, and the resulting mixture was extracted withethyl acetate (20mL×3). The extract was washed with brine,dried over anhydrous magnesium sulfate, and evaporated. Chromatography on silica gel using n-hexane/ethyl acetate as the eluent gave the sulfonyl fluoride ( 3b) (299.0mg, 86%) as colorless crystals
	Multi-step reaction with 2 steps 1: Selectfluor™ / acetonitrile; water / 0.02 h / 20 °C 2: Selectfluor™ / acetonitrile; water / 1 h / 20 °C / Reflux

Reference： [1]Location in patent: experimental part Kirihara, Masayuki; Naito, Sayuri; Ishizuka, Yuki; Hanai, Honoka; Noguchi, Takuya [Tetrahedron Letters, 2011, vol. 52, # 24, p. 3086 - 3089]
[2]Kirihara, Masayuki; Naito, Sayuri; Nishimura, Yuki; Ishizuka, Yuki; Iwai, Toshiaki; Takeuchi, Haruka; Ogata, Tomomi; Hanai, Honoka; Kinoshita, Yukari; Kishida, Mari; Yamazaki, Kento; Noguchi, Takuya; Yamashoji, Shiro [Tetrahedron, 2014, vol. 70, # 14, p. 2464 - 2471]
[3]Kirihara, Masayuki; Naito, Sayuri; Nishimura, Yuki; Ishizuka, Yuki; Iwai, Toshiaki; Takeuchi, Haruka; Ogata, Tomomi; Hanai, Honoka; Kinoshita, Yukari; Kishida, Mari; Yamazaki, Kento; Noguchi, Takuya; Yamashoji, Shiro [Tetrahedron, 2014, vol. 70, # 14, p. 2464 - 2471]

30
[ 5335-87-5 ]
[ 28075-50-5 ]
[ 1351526-37-8 ]

Yield	Reaction Conditions	Operation in experiment
95%	With [RhCl₂(p-cymene)]2; 3,4,7,8-Tetramethyl-o-phenanthrolin; zinc In 1,3-dimethyl-2-imidazolidinone at 120℃; for 24h; Inert atmosphere;	3.2. General procedure for ruthenium-catalyzed reaction of alkenyl electrophiles with zinc thiolates General procedure: To a mixture of [RuCl2(p-cymene)]2 (2.3 mg, 3.8 μmol), 3,4,7,8-tetramethyl-1,10-phenanthroline (1.8 mg, 7.5 μmol), zinc powder (18.8 mg, 0.288 mg atom), a disulfide (0.25 mmol), and DMI (1.0 mL) placed in a flame-dried 20 mL Schlenk tube was added an alkenyl electrophile (0.25 mmol). After stirring at 120 °C for 24 h, the reaction mixture was extracted with diethyl ether (3×10 mL). The combined organic layer was washed with water (2×15 mL) and brine (15 mL), and dried over MgSO4. After filtration and evaporation, the crude product was subjected to column chromatography on silica gel (hexane/NEt3 97:3) or alumina (hexane) to give the corresponding product.
10%	With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; tetrabutylammonium acetate In N,N-dimethyl acetamide at 20℃; for 2h; Glovebox; Electrochemical reaction; Inert atmosphere; chemoselective reaction;

Reference： [1]Location in patent: experimental part Imazaki, Yusuke; Shirakawa, Eiji; Hayashi, Tamio [Tetrahedron, 2011, vol. 67, # 52, p. 10212 - 10215]
[2]Zhang, Feng; Wang, Yang; Wang, Yi; Pan, Yi [Organic Letters, 2021, vol. 23, # 19, p. 7524 - 7528]

31
[ 5335-87-5 ]
[ 120068-79-3 ]
[ 1158997-65-9 ]

Reference： [1]Synthetic Communications,2012,vol. 42,p. 3472 - 3481

32
[ 5335-87-5 ]
[ 402-31-3 ]
[ 1393715-59-7 ]

Yield	Reaction Conditions	Operation in experiment
81%	Stage #1: 1,3-bis(trifluoromethyl)benzene With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; bis(pinacol)diborane; 4,4'-di-tert-butyl-2,2'-bipyridine In tetrahydrofuran at 80℃; for 24h; Inert atmosphere; Stage #2: 4,4'-dimethoxyphenyl disulfide With [2,2]bipyridinyl; copper(l) chloride In water; dimethyl sulfoxide at 80℃; for 24h; Inert atmosphere; regioselective reaction;

Reference： [1]Cheng, Jun-Hao; Yi, Chih-Lun; Liu, Tsung-Jui; Lee, Chin-Fa [Chemical Communications, 2012, vol. 48, # 67, p. 8440 - 8442]

33
[ 5335-87-5 ]
[ 66176-17-8 ]
[ 1423629-66-6 ]

Yield	Reaction Conditions	Operation in experiment
84%	With sodium dithionite; water; potassium carbonate; In dimethyl sulfoxide; at 60℃; for 0.75h;	General procedure: A mixture of isatoic anhydride 1 (0.6 mmol), disulfide 2 (0.2 mmol), and Na2S2O4 (0.9 mmol) in undried DMSO (2 mL) was stirred at 60 C for respective time in Table 2 and Scheme 2. After the completion of the reaction, as monitored by TLC and GC-MS analysis, the reaction mixture washed with brine and extracted with ethyl acetate. The organic phase was separated and dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated and the resulting residue was purified by column chromatography on silica gel (300-400 mesh) with petroleum ether-EtOAc as eluent to provide the desired product.

Reference： [1]Tetrahedron,2013,vol. 69,p. 2283 - 2288

34
[ 40928-13-0 ]
[ 5335-87-5 ]
[ 1423629-72-4 ]

Yield	Reaction Conditions	Operation in experiment
81%	With sodium dithionite; water; potassium carbonate; In dimethyl sulfoxide; at 60℃; for 1.25h;	General procedure: A mixture of isatoic anhydride 1 (0.6 mmol), disulfide 2 (0.2 mmol), and Na2S2O4 (0.9 mmol) in undried DMSO (2 mL) was stirred at 60 C for respective time in Table 2 and Scheme 2. After the completion of the reaction, as monitored by TLC and GC-MS analysis, the reaction mixture washed with brine and extracted with ethyl acetate. The organic phase was separated and dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated and the resulting residue was purified by column chromatography on silica gel (300-400 mesh) with petroleum ether-EtOAc as eluent to provide the desired product.

Reference： [1]Tetrahedron,2013,vol. 69,p. 2283 - 2288

35
[ 18474-57-2 ]
[ 5335-87-5 ]
[ 1429474-35-0 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 3235 - 3246

36
[ 3240-34-4 ]
[ 5335-87-5 ]
[ 19955-99-8 ]
[ 1455451-48-5 ]

Yield	Reaction Conditions	Operation in experiment
72%	With potassium iodide; In dichloromethane; at 20℃;	General procedure: DIB (0.6 mmol, 193 mg), ArSSAr (0.3 mmol), and KI (0.5 mmol, 83 mg) were added to a styrene (or their derivatives) solution in CH2Cl2 (0.5 mmol in 2 mL of CH2Cl2), and the suspension mixture was vigorously stirred at room temperature for 2 h. Upon completion, the reaction mixture was quenched by the addition of saturated aqueous sodium thiosulfate (Na2S2O3) (5 mL), and basified with saturated aqueous sodium hydrogen carbonate (NaHCO3) (5 mL). Further stirring was followed by extraction with ethyl acetate (3*15 mL). The combined organic extracts were washed with water (20 mL), brine (20 mL), dried (anhydrous MgSO4), filtered, and concentrated (aspirator). The residue was purified by column chromatography (SiO2) to furnish analytically pure product. 4.2.25 1-(3-Formylphenyl)-2-((4-methoxyphenyl)thio)ethyl acetate (3kc) m-Vinylbenzaldehyde (1k) (67 mg, 0.50 mmol). Column chromatography (silica gel; 5-12% EtOAc/hexanes) yields 3kc (119 mg, 72%); light yellow viscous oil; Rf (20% EtOAc/hexanes) 0.26; IR (neat): νmax 2730, 1743, 1699, 1246 cm-1; 1H NMR (300 MHz, CDCl3): δ 9.98 (s, 1H, CHO), 7.82-7.76 (m, 2H, ArH), 7.56 (dt, J=7.8, 1.5 Hz, 1H, ArH), 7.49 (br t, J=7.8 Hz, 1H, ArH), 7.34 (br d, J=8.8 Hz, 2H, ArH), 6.83 (br d, J=8.8 Hz, 2H, ArH), 5.88 (dd, J=7.7, 5.8 Hz, 1H, ArCH), 3.78 (s, 3H, OCH3), 3.32 (dd, J=14.0, 7.7 Hz, 1H, CHH), 3.14 (dd, J=14.0, 5.8 Hz, 1H, CHH), 2.06 (s, 3H, CH3); 13C NMR (75 MHz, CDCl3): δ 191.8, 169.8, 159.2, 140.2, 136.4, 133.9, 132.7, 129.7, 129.1, 127.5, 125.0, 114.6, 73.8, 55.2, 41.7, 20.9; HRMS (ESI-TOF): MNa+, found: 353.0834; error=3 ppm requires C18H18NaO4S 353.0823.

Reference： [1]Tetrahedron,2013,vol. 69,p. 8847 - 8856

37
[ 5335-87-5 ]
[ 141-97-9 ]
[ 28743-98-8 ]

Reference： [1]Advanced Synthesis and Catalysis,2013,vol. 355,p. 2558 - 2563

38
[ 95-20-5 ]
[ 5335-87-5 ]
[ 1021422-61-6 ]

Yield	Reaction Conditions	Operation in experiment
96%	With sodium tetrafluoroborate; potassium iodide In acetonitrile at 60℃; for 6h; Electrolysis;	Electrosynthesis of 3-sulfenylindoles General procedure: The electrochemical experiment was performed on 263A Potentiostat/Galvanostat (PrincetonApplied Research, USA) in a 25 mL undivided cell. Two graphite rods(6mmin diameter, 1 cm in length) were employed as the working electrode and the counter electrode respectively. The reference electrode was Ag/Ag+ electrode (0.1 mol/L AgNO3 in CH3CN). 2-Methylindole(1a, 1.0 mmol), diphenyl disulfide (2a, 0.5 mmol) and KI (0.05 mmol) were added into 0.1 mol/L of NaBF4/CH3CN solution (15 mL)with stirring at 60°C. The electrolysis reactions were operated at 0.4V. After completion of the reaction (monitored by GC or TLC), the resulting mixture was concentrated under reduced pressure and purified by column chromatography on silica gel using hexanes/EtOAc(100:1) as eluent to afford 2-methyl-3-(phenylthio)-indole (3aa) as a white solid in 94% yield.
96%	With sodium tetrafluoroborate; potassium iodide In acetonitrile at 60℃; for 6h; Electrochemical reaction;	22 Example 22: Preparation of 2-methyl-3-p-methoxyphenylthio-1H-indole (Formula 7) Add in a 30ml beaker 0.1 mol/L sodium tetrafluoroborate in acetonitrile (15 mL), 2-methyl-1H-indole (1 mmol), bis(p-methoxyphenyl)disulfide (0.5 mmol) and potassium iodide (0.05 mmol). Constant potential electrolysis at 60 ° C, 0.4 V, and the reaction was completed after 6 h. The solvent is distilled off under reduced pressure, and then subjected to column chromatography, and the mixture of ethyl acetate/n-hexane volume ratio of 1:100 is used as an eluent, and the eluent containing the target compound is collected, and the solvent is distilled off to obtain the product 2-Methyl-3-p-methoxyphenylthio-1H-indole. The isolated yield was 96%.
79%	Stage #1: 4,4'-dimethoxyphenyl disulfide With ammonium peroxydisulfate In methanol at 70℃; for 3h; Stage #2: 2-methyl-1H-indole In methanol at 20 - 70℃;

78%

With sodium iodide In acetonitrile at 20℃; for 18h; Irradiation;

Preparation of the benzothiazole 3a General procedure: To a 20 mL glass tube with a stir bar was charged 2-methyl-1H-indole 1a (39.35 mg, 0.3 mmol), diphenyldisulfide 2a (65.50 mg, 0.3 mmol), NaI (0.06 mmol, 9 mg) and MeCN (2 mL). The solution was stirred at room temperature with the irradiation of a 12 W blue LED for 18 h. The solvent was removed under vacuum. The residue was purified by column chromatography over silica gel (petroleum ether/ethyl acetate = 15/1) to give the product 3a (60 mg, 83%).

Reference： [1]Chen, Chen; Niu, Pengfei; Shen, Zhenlu; Li, Meichao [Journal of the Electrochemical Society, 2018, vol. 165, # 5, p. G67 - G74]
[2]Current Patent Assignee: ZHEJIANG UNIVERSITY OF TECHNOLOGY - CN107620088, 2019, B Location in patent: Paragraph 0067-0068
[3]Prasad, Ch. Durga; Kumar, Shailesh; Sattar, Moh.; Adhikary, Amit; Kumar, Sangit [Organic and Biomolecular Chemistry, 2013, vol. 11, # 46, p. 8036 - 8040]
[4]Ye, Lin-miao; Chen, Jie; Mao, Peng; Zhang, Xue-jing; Yan, Ming [Tetrahedron Letters, 2017, vol. 58, # 28, p. 2743 - 2746]

39
[ 5720-07-0 ]
[ 5335-87-5 ]

Yield	Reaction Conditions	Operation in experiment
95%	With copper (II)-fluoride; sulfur In dimethyl sulfoxide at 100℃; for 12h; Inert atmosphere;
85%	With sulfur; silver nitrate In dimethyl sulfoxide at 120℃; for 24h; Inert atmosphere;	5 Synthesis of 1,2-bis(4-methoxyphenyl) disulfide compound At room temperature, add 4-methoxyphenylboronic acid (0.4mmol, 1.0equiv), sulfur powder (1.2mmol, 3.0equiv), silver nitrate (0.08mmol, 0.2equiv) and 2mL dimethyl sulfoxide into the reaction tube , And then pumped-filled with nitrogen, and replaced three times, tightened with a Teflon stopper,Stir at 120°C reaction temperature for 24h. The reaction mixture was cooled, and then water and ethyl acetate were added for extraction, dried over anhydrous sodium sulfate, filtered to a chicken heart bottle, and then the solvent was spun off.The product was separated by column chromatography (eluent: petroleum ether: ethyl acetate 8: 2),The product is a yellow liquid, the yield is 85%, and the product weight is 47 mg.
84%	With CrPOM; sodium thiosulfate In water; toluene at 100℃; for 24h;

66%

Stage #1: 4-methoxyphenylboronic acid With acetamide; sodium metabisulfite; C₂₃H₃₁NP⁽¹⁺⁾*Cl^(1-); choline chloride; palladium dichloride at 80℃; for 12h; Green chemistry; Stage #2: With iodine for 0.333333h; Green chemistry;

Reference： [1]Yu, Jin-Tao; Guo, Huan; Yi, Yuanqiuqiang; Fei, Haiyang; Jiang, Yan [Advanced Synthesis and Catalysis, 2014, vol. 356, # 4, p. 749 - 752]
[2]Current Patent Assignee: WENZHOU MEDICAL UNIVERSITY - CN111892519, 2020, A Location in patent: Paragraph 0066-0075
[3]Chang, Yalin; Li, Huiyi; Tao, Chaofu; Wang, Aiping; Wei, Yongge; Xie, Ya; Yu, Han; Yu, Shunming [Green Chemistry, 2021, vol. 23, # 16, p. 6059 - 6064]
[4]Marset, Xavier; Guillena, Gabriela; Ramón, Diego J. [Chemistry - A European Journal, 2017, vol. 23, # 44, p. 10522 - 10526]

40
[ 5335-87-5 ]
[ 2297-24-7 ]

Yield	Reaction Conditions	Operation in experiment
87%	With N-Bromosuccinimide In water; acetonitrile at 20℃; for 0.25h;	Representative experimental procedure to prepare sulfonylbromide from disulfides General procedure: In a 10mL round bottom flask, p-tolyl disulfide ( 1b) (246.3mg, 1.0mmol) was dissolved in acetonitrile (2.0mL) and water (0.2mL). The round bottom flask was covered with aluminum foil to shield it from light. N-Bromosuccinimide (1068mg, 6.0mmol) was added to the mixture, and the resulting mixture was stirred at room temperature for 3h. Water (10mL) was added and the resulting mixture was extracted with ethyl acetate (20mL×3). The extract was washed with brine, dried over anhydrous magnesium sulfate, and evaporated. Chromatography on silica gel using n-hexane/ethyl acetate as the eluent gave the sulfonyl bromide ( 5b) (371.4mg, 79%) as colorless crystals.
84%	With sodium hypochlorite pentahydrate; acetic acid; sodium bromide for 0.666667h;	4 An eggplant flask was charged with 1.08 g (6.5 mmol) of sodium hypochlorite pentahydrate,0.83 g (8.0 mmol) of sodium bromide, and 8 mL of acetic acid, and the mixture was stirred at room temperature for 20 minutes. Thereafter, an aluminum foil was wound around a recovery flask, and 0.278 g (1.0 mmol) of bis (p-methoxyphenyl) disulfide as a raw material was added, And the reaction was allowed to proceed for 40 minutes with stirring after completion of the raw material addition.After completion of the reaction, 50 mL of water was added to the obtained reaction mixture, salts in the reaction mixture were dissolved in an aqueous phase, then extracted with chloroform three times, anhydrous magnesium sulfate was added to the organic phase, dried and dried, After that, the solvent was distilled off to obtain 0.5722 g of a crude product.The obtained crude product was purified by column chromatography (silica gel mesh 40 to 50 μm, column φ = 2 cm, developing solvent Hexane: AcOEt = 10: 1, used test tube = 1.5 × 10 cm) to obtain (P-methoxyphenyl) sulfonyl bromide 0.4193 g (1.7 mmol, yield 84%).

Reference： [1]Kirihara, Masayuki; Naito, Sayuri; Nishimura, Yuki; Ishizuka, Yuki; Iwai, Toshiaki; Takeuchi, Haruka; Ogata, Tomomi; Hanai, Honoka; Kinoshita, Yukari; Kishida, Mari; Yamazaki, Kento; Noguchi, Takuya; Yamashoji, Shiro [Tetrahedron, 2014, vol. 70, # 14, p. 2464 - 2471]
[2]Current Patent Assignee: NIPPON LIGHT METAL HOLDINGS COMPANY, LTD. - JP2017/52728, 2017, A Location in patent: Paragraph 0027; 0028

41
[ 5335-87-5 ]
[ 15015-57-3 ]
[ 1068439-17-7 ]

Yield	Reaction Conditions	Operation in experiment
	In water; acetonitrile; at 25℃; for 9h;Irradiation;	Equimolar quantities of aryl disulfide-containing compounds 1 (31.3 mg, 0.125 mmol) and 2 (34.8 mg, 0.125 mmol) were mixed in solvent (acetonitrile/water = 7/3, v/v) as a 0.05 mol L-1 solution. The solution was charged in a quartz cell. Then, the cell was exposed to UV light (AS ONE corporation, SLUV-8; 9 W UV lamp with 254 nm, 50 mm sample-to-light distance) for 9 h at room temperature. The reaction was followed by HPLC (eluent: acetonitrile/water = 7/3, v/v).

Reference： [1]Chemistry Letters,2013,vol. 42,p. 1346 - 1348

42
[ 5929-72-6 ]
[ 5335-87-5 ]
(3Z)-3-[(4-methoxyphenyl)sulfanyl]-2,7-dimethyloct-3-en-5-yne-2,7-diol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With rongalite; potassium carbonate In water; N,N-dimethyl-formamide at 40℃; for 3h; Green chemistry; stereoselective reaction;	(Z)-1-Sulfanyl or -selanylalk-1-en-3-ynes 5; General Procedure General procedure: To a well-stirred solution of 1,4-diorganylbuta-1,3-diyne (0.5 mmol, 1 equiv) in DMF-H2O (20:1; 4 mL), the disulfide/diselenide (0.25 mmol, 0.5 equiv) was added followed by the addition of rongalite 2 (1.5 mmol, 3 equiv) and K2CO3 (1 mmol, 2 equiv). The mixture was stirred at 40 °C or 50 °C for the time indicated in Table 2 or 3. Completion of the reaction was monitored by TLC until consumption of the starting material. The mixture was allowed to attain r.t. and water was added followed by extraction with EtOAc (2 × 20 mL). The organic layer was separated, then washed with brine, extracted with EtOAc (2 × 5 mL), and dried (anhyd Na2SO4). The solvent was evaporated under vacuum and the crude product was purified by column chromatography (silica gel, 230-400 mesh, EtOAc-petroleum ether).

Reference： [1]Venkateswarlu, Cheerladinne; Chandrasekaran, Srinivasan [Synthesis, 2015, vol. 47, # 3, p. 395 - 410]

43
[ 5335-87-5 ]
[ 171667-56-4 ]
(2Z)-2-[(4-methoxyphenyl)sulfanyl]undec-2-en-4-yn-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With rongalite; potassium carbonate In water; N,N-dimethyl-formamide at 40℃; for 3h; Green chemistry; stereoselective reaction;	(Z)-1-Sulfanyl or -selanylalk-1-en-3-ynes 5; General Procedure General procedure: To a well-stirred solution of 1,4-diorganylbuta-1,3-diyne (0.5 mmol, 1 equiv) in DMF-H2O (20:1; 4 mL), the disulfide/diselenide (0.25 mmol, 0.5 equiv) was added followed by the addition of rongalite 2 (1.5 mmol, 3 equiv) and K2CO3 (1 mmol, 2 equiv). The mixture was stirred at 40 °C or 50 °C for the time indicated in Table 2 or 3. Completion of the reaction was monitored by TLC until consumption of the starting material. The mixture was allowed to attain r.t. and water was added followed by extraction with EtOAc (2 × 20 mL). The organic layer was separated, then washed with brine, extracted with EtOAc (2 × 5 mL), and dried (anhyd Na2SO4). The solvent was evaporated under vacuum and the crude product was purified by column chromatography (silica gel, 230-400 mesh, EtOAc-petroleum ether).

Reference： [1]Venkateswarlu, Cheerladinne; Chandrasekaran, Srinivasan [Synthesis, 2015, vol. 47, # 3, p. 395 - 410]

44
[ 591-50-4 ]
[ 5335-87-5 ]
[ 5633-57-8 ]

Yield	Reaction Conditions	Operation in experiment
93%	With copper(l) iodide; 2,6-bis(2'-pyridyl)-4-(p-methoxyphenyl)pyridine; potassium hydroxide In dimethyl sulfoxide at 110℃; for 15h; Inert atmosphere; chemoselective reaction;	General procedure for the preparation of diorgano chalcogenides General procedure: A flame-dried test tube containing a magnetic stirringbar was charged with diorgano dichalcogenide (0.5 mmol), arylhalide (1.0 mmol), KOH (1.0 mmol), and anhydrous DMSO (2mL) [for aryl bromides or chlorides, TBAB (1.0 mmol) was alsoadded]. Then, CuI (10 mol%) and Mtpy (10 mol%) were added tothe above mixture, and the reaction mixture was heated at110 °C under nitrogen. The progress of the reaction was monitoredby TLC. Upon completion of the reaction, the mixture wascooled to r.t., poured into H2O (10 mL), and extracted withEtOAc (3 × 8 mL). The combined organic layers were dried overMgSO4, filtered, and concentrated in vacuo to give the crudeproduct, which was further purified by preparative TLC (silicagel; n-hexane-EtOAc, 9:1). The identities of the products wereconfirmed by IR, 1H and 13C NMR spectroscopic analysis.
98 %Chromat.	With potassium carbonate In dimethyl sulfoxide at 110℃; for 12h;

Reference： [1]Movassagh, Barahman; Hosseinzadeh, Zhila [Synlett, 2016, vol. 27, # 5, p. 777 - 781]
[2]Fu, Wenqian; Liu, Taotao; Fang, Zhongxue; Ma, Yuli; Zheng, Xiang; Wang, Wenchang; Ni, Xiaojun; Hu, Maolin; Tang, Tiandi [Chemical Communications, 2015, vol. 51, # 27, p. 5890 - 5893]

45
[ 7008-63-1 ]
[ 5335-87-5 ]
5-[(4-methoxyphenyl)thio]-6-phenylimidazo[2,1-b]thiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With dihydrogen peroxide; iodine In ethanol at 25℃; for 18h; Green chemistry;	6-Phenyl-5-(phenylthio)imidazo[2,1-b]thiazole (3aa);^20dTypicalProcedure General procedure: A 15-mL tube with a Teflon cap, equipped with a magnetic stirring bar, was charged with substrate 1a (0.20 mmol), diphenyl disulfide (0.10 mmol, 0.5 equiv), and I2 (20 mol %); H2O2 (2 equiv) and EtOH (2mL) were then added sequentially. The tube was capped and stirred at 25 °C for 18 h, the crude mixture was diluted with EtOAc, and washed with sat. aq Na2S2O3 solution (3 × 10 mL). The organic phase was dried (MgSO4), filtered through a Celite pad, and washed with EtOAc. The filtrate was concentrated in vacuo, and the resulting residue was purified by column chromatography (hexane - EtOAc) to afford product 3aa as a light yellow solid; yield: 56.8 mg (92%).

Reference： [1]Ji, Xiao-Ming; Zhou, Shu-Juan; Chen, Fan; Zhang, Xing-Guo; Tang, Ri-Yuan [Synthesis, 2015, vol. 47, # 5, p. 659 - 671]

46
[ 1455-20-5 ]
[ 5335-87-5 ]
2-butyl-5-((4-methoxyphenyl)thio)thiophene [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 5772 - 5776
Angew. Chem.,2015,vol. 127,p. 5864 - 5868,5
Angewandte Chemie,2015,vol. 127,p. 5864 - 5868,5

47
[ 1142-19-4 ]
[ 5335-87-5 ]
1-(4-chlorophenyl)-2-(4-methoxyphenyl)disulfane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With N-iodo-succinimide In acetonitrile at 20℃; for 1h;
71%	With N-fluorobis(benzenesulfon)imide In 1,2-dichloro-ethane at 50℃; for 4h; Schlenk technique; Sealed tube;	General procedure: 25 mL Schlenk tube was charged with RSSR 1 (0.2 mmol), R'SSR' 1' (0.4 mmol), NFSI (0.02 mmol) and DCE (2.0 mL). The tube was sealed and the reaction was then stirred vigorously at 50 C for 4 h. After cooling to room temperature, the reaction mixture was then concentrated in vacuo, and the crude product was purified by flash chromatography on silica gel to yield the product 4 (isolated yields are based on 0.4 mmol of 4).
53%	With H₃N*C₂H₆O₆S₂; tetrabutylammonium tetrafluoroborate; silver(I) acetate In dimethyl sulfoxide at 20℃; for 48h;

Reference： [1]Mal, Prasenjit; Mathuri, Ashis; Parida, Amarchand; Pramanik, Milan [Organic and Biomolecular Chemistry, 2021, vol. 19, # 39, p. 8539 - 8543]
[2]Hu, Qingyue; Li, Zheng-Yi; Song, Mengjie; Sun, Xiaoqiang; Yang, Ke [Chinese Chemical Letters, 2022]
[3]Zhang, Cheng; McClure, Jesse; Chou, C. James [Journal of Organic Chemistry, 2015, vol. 80, # 10, p. 4919 - 4927]

48
[ 5335-87-5 ]
[ 123-54-6 ]
[ 935667-85-9 ]

Yield	Reaction Conditions	Operation in experiment
99%	With dipotassium peroxodisulfate; iodine In neat (no solvent) at 20℃; for 48h;
94%	Stage #1: 4,4'-dimethoxyphenyl disulfide With tetrabutylammomium bromide; triethylamine In dichloromethane for 1h; Cooling with ice; Stage #2: acetylacetone In dichloromethane at 20℃; for 1.5h;	Typical procedure for the preparation of 3 (3a as an example) General procedure: A mixture of diaryl disulfide 1a (0.5 mmol, 154 mg), TBATB (1 mmol, 482 mg) and Et3N (1.2 mmol, 0.17 mL) in anhydrous CH2Cl2 (10 mL) was stirred for 30 min in an ice water bath. After 30 min 2a (1.2 mmol, 0.12 mL) was added and the reaction mixture was stirred for additional 1.5 h at room temperature. After completion of the reaction monitored by TLC the reaction mixture was diluted by distilled water. The mixture was extracted with CH2Cl2. The organic layer was separated, dried over Na2SO4 and concentrated under vacuum. The reaction mixture was purified by column chromatography on silica gel using hexane/ethyl acetate (9:1) to give the desired product.
58%	Stage #1: 4,4'-dimethoxyphenyl disulfide With dimethyl sulfoxide at 40℃; for 0.25h; Green chemistry; Stage #2: acetylacetone With iodine; triethylamine Green chemistry; regioselective reaction;

Reference： [1]Liu, Yi-Wei; Badsara, Satpal Singh; Liu, Yi-Chen; Lee, Chin-Fa [RSC Advances, 2015, vol. 5, # 55, p. 44299 - 44305]
[2]Rahaman, Rajjakfur; Devi, Namita; Barman, Pranjit [Tetrahedron Letters, 2015, vol. 56, # 28, p. 4224 - 4227]
[3]Devi, Namita; Rahaman, Rajjakfur; Sarma, Kuladip; Barman, Pranjit [European Journal of Organic Chemistry, 2016, vol. 2016, # 2, p. 384 - 388]

49
[ 914785-45-8 ]
[ 5335-87-5 ]
3-((4-methoxyphenyl)thio)-1-methyl-4-phenyl-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With oxygen; copper dichloride In water; N,N-dimethyl-formamide at 100℃; for 24h;	Typical experimental procedure for the Copper-Catalyzed Oxidative ispo-Cyclization to access 3-Arylthio spiro[4,5]trienones General procedure: To a Schlenk tube were added N-(p-methoxyaryl)propiolamide1a (0.2 mmol), 1,2-diphenyldisulfane (2a, 1.5 equiv), H2O (2equiv), CuCl2 (10 mol%), and DMF (anhydrous; 2 mL). Then thetube was charged with oxygen and was stirred at 100 °C for 24h until complete consumption of starting material as monitoredby TLC and/or GC-MS analysis. After the reaction was finished,the reaction mixture was washed with brine. The aqueousphase was re-extracted with EtOAc. The combined organicextracts were dried over Na2SO4, concentrated in vacuum, andthe resulting residue was purified by silica gel column chromatography(hexane-EtOAc) to afford the desired product 3.
	With Selectfluor In acetonitrile at 40℃; for 1.5h;	4.3 Synthesis of 3-arylthio azaspiro[4,5]trienones (5) General procedure: N-(4-Methoxyphenyl)-N-methyl-3-phenylpropiolamide 1a (0.2 mmol,53.0 mg), diaryldisulfides 4 (0.2 mmol), Selectfluor agent (0.2 mmol,70.8 mg), and acetonitrile (2.0 mL) were added to a 10 mL reactiontube. The mixture was stirred at 40 °C for 1.5 h. After completion of thereaction, the solvent was distilled under vacuum. Then, the resultingmixture was dissolved with ethyl acetate (15 mL), washed with saturatedsodium chloride solution (10 mL × 2). The organic phase wasdried over anhydrous Na2SO4 and concentrated under vacuum. Theresidue was purified by silica gel column chromatography to give3-arylthio azaspiro[4,5]trienones 5 using ethyl acetate/dichloromethaneas eluant.

Reference： [1]Qian, Peng-Cheng; Liu, Yu; Song, Ren-Jie; Xiang, Jian-Nan; Li, Jin-Heng [Synlett, 2015, vol. 26, # 9, p. 1213 - 1216]
[2]Yuan, Jin-Wei; Huang, Guang-Chao; Wang, Li-Li; Wang, Xin-Yuan; Yang, Liang-Ru; Zhang, Shou-Ren; Mao, Pu; Xiao, Yong-Mei; Qu, Ling-Bo [Zeitschrift fur Naturforschung, B: Chemical Sciences, 2022, vol. 77, # 1, p. 75 - 85]

50
[ 5335-87-5 ]
[ 105-36-2 ]
[ 28743-98-8 ]

Yield	Reaction Conditions	Operation in experiment
84%	With [{Ti(salophen)H2O}2O][OSO2C4F9]2; zinc; In tetrahydrofuran; at 20℃; for 2h;Inert atmosphere;	General procedure: Under N2 atmosphere, a solution of complex 1 (68.7 mg, 5 mol%) in THF (3.0 mL), zinc dust (80 mg, 1.2 mmol), diphenyl disulfide (109 mg, 0.5 mmol), and ethyl 2-bromoacetate (184 mg, 1.1 mmol) were added. Then the mixture was stirred for 2 h at room temperature, monitored by thin-layer chromatography (TLC). The resulting reaction mixture was diluted with diethyl ether (10 mL x 3), filtered, and evaporated, and then the residue was subjected to column chromatography using petroleum ether:ethyl acetate as eluent (30:1) to afford the pure product 6a.
70%	With iron; In N,N-dimethyl-formamide; at 90℃; for 20h;Inert atmosphere;	General procedure: In a round-bottomed flask, activated iron dust (168 mg,3 mmol) was added to a solution of α-bromo carbonyl compounds (1.0 mmol) and diaryl disulfides (0.5 mmol) in DMF (3.0mL). The reaction mixture was stirred at 90C under N2 atmosphere for 15 h. Then ethyl acetate (20 mL) was added, stirred, and filtered. To filter liquor, the water (15 mL) was added and the mixture was extracted with ethyl acetate (15 mL × 3). The combined organic phase was washed with water (20 mL × 2), dried over anhydrous Na2SO4 , and concentrated under vacuum. The crude product was purified by column chromatography on silica gel (petroleum ether /ethyl acetate = 30:1).

Reference： [1]Tetrahedron,2020,vol. 76
[2]Synthetic Communications,2015,vol. 45,p. 1817 - 1822

51
[ 1002-28-4 ]
[ 201230-82-2 ]
[ 5335-87-5 ]
(Z)-3-{1-(4-methoxyphenylthio)propylidene}dihydrofuran-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾ In toluene at 140℃; for 20h; Inert atmosphere; Autoclave; regioselective reaction;

Reference： [1]Higashimae, Shinya; Tamai, Taichi; Nomoto, Akihiro; Ogawa, Akiya [Journal of Organic Chemistry, 2015, vol. 80, # 14, p. 7126 - 7133]

52
[ 170891-76-6 ]
[ 5335-87-5 ]
5-(4-methoxyphenylmercapto)-8-(trimethylacetamido)quinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With oxygen; copper(ll) bromide In N,N-dimethyl-formamide at 160℃; for 24h;	15 Preparation Example 15 Add 0.25 mmol of 8-(trimethylacetamido)quinoline (R1=tert-butyl), 0.3 mmol of p-methoxyphenyldisulfide (R2=p-OMePh), CuBr2 0.5 mmol and 1 mL of DMF to a 10 mL reaction tube. The reaction was carried out at 160 ° C for 24 h under an oxygen atmosphere. After completion of the reaction, filtration, concentration and separation by column chromatography gave 5-(4-methoxyphenylmercapto)-8-(trimethylacetamido)quinoline in a yield of 95%.
93%	With oxygen; copper(ll) bromide In N,N-dimethyl-formamide at 160℃; for 24h; Schlenk technique; regioselective reaction;

Reference： [1]Current Patent Assignee: HUNAN UNIVERSITY - CN105175330, 2018, B Location in patent: Paragraph 0049; 0050
[2]Zhu, Longzhi; Qiu, Renhua; Cao, Xin; Xiao, Song; Xu, Xinhua; Au, Chak-Tong; Yin, Shuang-Feng [Organic Letters, 2015, vol. 17, # 22, p. 5528 - 5531]

53
[ 5335-87-5 ]
[ 93107-30-3 ]
1-cyclopropyl-6,7-difluoro-3-((4-methoxyphenyl)thio)quinolin-4(1H)-one [ No CAS ]

Reference： [1]Chemistry - An Asian Journal,2016,vol. 11,p. 360 - 366

54
[ 5335-87-5 ]
[ 82419-35-0 ]
9,10-difluoro-6-((4-methoxyphenyl)thio)-3-methyl-2H-[1,4]oxazino[2,3,4-ij]quinolin-7(3H)-one [ No CAS ]

Reference： [1]Chemistry - An Asian Journal,2016,vol. 11,p. 360 - 366

55
[ 5335-87-5 ]
[ 68077-26-9 ]
7-chloro-1-ethyl-6-fluoro-3-((4-methoxyphenyl)thio)quinolin-4(1H)-one [ No CAS ]

Reference： [1]Chemistry - An Asian Journal,2016,vol. 11,p. 360 - 366

56
[ 696-63-9 ]
[ 20532-30-3 ]
[ 5335-87-5 ]

Reference： [1]Helvetica Chimica Acta,2016,vol. 99,p. 384 - 392

57
[ 91906-21-7 ]
[ 20532-30-3 ]
[ 5335-87-5 ]

Reference： [1]Helvetica Chimica Acta,2016,vol. 99,p. 384 - 392

58
[ 102-86-3 ]
[ 5335-87-5 ]
2,2-bis((4-methoxyphenyl)thio)hexanal [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With iodine; sodium carbonate In dimethyl sulfoxide at 100℃; for 24h; Green chemistry;	10 Specific Example 10: Ar p-methoxyphenyl, 1: 2, trihexylamine, A mixture of 55.7 mg (0.2 mmol) of di-p-methoxyphenyl disulfide, 107.8 mg (0.4 mmol) of trihexylamine, 42.4 mg (0.4 mmol) of Na2CO3, 101.6 mg (0.4 mmol) of iodine was added in the reaction tube, 2 ml of DMSO was added , heated at 100OC for 24 hours. After completion of the reaction was cooled, filtered, and the filtrate was rotary evaporated to remove the solvent, the residue was purified by silica gel column chromatography, petroleum ether The solvent was removed by evaporation on a rotary evaporator and dried in vacuo to give 39.9 mg of 2,2-di-p-methoxyphenylthiohexanal in 53% yield as yellowish liquid.
53%	With iodine; sodium carbonate In dimethyl sulfoxide at 100℃; for 24h; Schlenk technique;	2. General Procedure for the Synthesis of 3-13. General procedure: Under air atmosphere, a reaction tube was charged with disulfide (0.2 mmol), Tertiary amine (0.4 mmol), I2 (0.4 mmol) Na2CO3 (0.4 mmol) and DMSO (2 mL). The vessel was sealed and heated at 100 °C (oil bath temperature) for 24 h and then cooled to room temperature. The reaction mixture was washed with saturated Na2S2O3(2 x 15 mL) and then brine (1 x 15 mL). After the aqueous layer was extracted with ethyl acetate, the combined organic layers were dried over anhydrous Na2SO4 and evaporated under vacuum. The residue was purified by flash column chromatography (hexane/ethyl acetate) to afford the desired products.

Reference： [1]Current Patent Assignee: WENZHOU UNIVERSITY - CN106187839, 2016, A Location in patent: Paragraph 0029
[2]Gao, Xu-Hong; Xu, Wei; Zhang, Xing-Guo; Deng, Chen-Liang [Synlett, 2017, vol. 28, # 7, p. 841 - 846]

59
[ 1116-76-3 ]
[ 5335-87-5 ]
2,2-bis((4-methoxyphenyl)thio)octanal [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41%	With iodine; sodium carbonate; In dimethyl sulfoxide; at 100℃; for 24h;Green chemistry;	A mixture of 55.7 mg (0.2 mmol) of di-p-methoxyphenyl disulfide, 141.5 mg (0.4 mmol) of <strong>[1116-76-3]trioctylamine</strong>, 42.4 mg (0.4 mmol) of Na2CO3, 101.6 mg (0.4 mmol) of iodine was added in the reaction tube, , 2 ml of DMSO was added , heated at 100OC for 24 hours. After completion of the reaction was cooled, filtered, and the filtrate was rotary evaporated to remove the solvent, the residue was purified by silica gel column chromatography, petroleum ether The mixture was evaporated and the solvent removed by evaporation on a rotary evaporator and dried in vacuo to give a yellow liquid 33.1 mg of 2,2-di-p-methoxyphenylsulfenyl octanal in 41% yield.
41%	With iodine; sodium carbonate; In dimethyl sulfoxide; at 100℃; for 24h;Schlenk technique;	General procedure: Under air atmosphere, a reaction tube was charged with disulfide (0.2 mmol), Tertiary amine (0.4 mmol), I2 (0.4 mmol) Na2CO3 (0.4 mmol) and DMSO (2 mL). The vessel was sealed and heated at 100 C (oil bath temperature) for 24 h and then cooled to room temperature. The reaction mixture was washed with saturated Na2S2O3(2 x 15 mL) and then brine (1 x 15 mL). After the aqueous layer was extracted with ethyl acetate, the combined organic layers were dried over anhydrous Na2SO4 and evaporated under vacuum. The residue was purified by flash column chromatography (hexane/ethyl acetate) to afford the desired products.

Reference： [1]Patent: CN106187839,2016,A .Location in patent: Paragraph 0030
[2]Synlett,2017,vol. 28,p. 841 - 846

60
[ 5335-87-5 ]
[ 100-37-8 ]
2,2-bis((4-methoxyphenyl)thio)acetaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With iodine; sodium carbonate; In dimethyl sulfoxide; at 100℃; for 24h;Schlenk technique;	General procedure: Under air atmosphere, a reaction tube was charged with disulfide (0.2 mmol), Tertiary amine (0.4 mmol), I2 (0.4 mmol) Na2CO3 (0.4 mmol) and DMSO (2 mL). The vessel was sealed and heated at 100 C (oil bath temperature) for 24 h and then cooled to room temperature. The reaction mixture was washed with saturated Na2S2O3(2 x 15 mL) and then brine (1 x 15 mL). After the aqueous layer was extracted with ethyl acetate, the combined organic layers were dried over anhydrous Na2SO4 and evaporated under vacuum. The residue was purified by flash column chromatography (hexane/ethyl acetate) to afford the desired products.

Reference： [1]Synlett,2017,vol. 28,p. 841 - 846

61
[ 7335-06-0 ]
[ 5335-87-5 ]
2,2-bis((4-methoxyphenyl)thio)acetaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With iodine; sodium carbonate; In dimethyl sulfoxide; at 100℃; for 24h;Schlenk technique;	General procedure: Under air atmosphere, a reaction tube was charged with disulfide (0.2 mmol), Tertiary amine (0.4 mmol), I2 (0.4 mmol) Na2CO3 (0.4 mmol) and DMSO (2 mL). The vessel was sealed and heated at 100 C (oil bath temperature) for 24 h and then cooled to room temperature. The reaction mixture was washed with saturated Na2S2O3(2 x 15 mL) and then brine (1 x 15 mL). After the aqueous layer was extracted with ethyl acetate, the combined organic layers were dried over anhydrous Na2SO4 and evaporated under vacuum. The residue was purified by flash column chromatography (hexane/ethyl acetate) to afford the desired products.

Reference： [1]Synlett,2017,vol. 28,p. 841 - 846

62
[ 5335-87-5 ]
[ 75980-60-8 ]
S-(4-methoxyphenyl) 2,4,6-trimethylthiobenzoate [ No CAS ]
[ 99234-85-2 ]

Yield	Reaction Conditions	Operation in experiment
87%; 96%	In dichloromethane; at 20℃; for 6h;Inert atmosphere; Sealed tube; Irradiation;	General procedure: TMDPO (3) (104.5 mg, 0.3 mmol), dichalcogenide 4 (0.3 mmol), and dry, degassed CH2Cl2 (0.6 mL) were placed in a sealed Pyrex NMR tube under an inert atmosphere, and the mixture was irradiated with a xenon lamp (500 W) for 6 h at r.t. The reaction mixture was then concentrated under reduced pressure, and the crude mixture was purified by gel permeation chromatography (eluent: CHCl3) to give the desired products.

Reference： [1]Synthesis,2017,vol. 49,p. 3558 - 3567

63
[ 491-38-3 ]
[ 5335-87-5 ]
3-((4-methoxyphenyl)thio)-4H-chromen-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With ammonium iodide In N,N-dimethyl acetamide at 135℃; for 12h; regioselective reaction;	2 General procedure for the synthesis of 3-sulfanyl-chromones 3 General procedure: 0.5 mL DMAC was added into the flask charged with 0.25 mmol of flavones, 0.25 mmol of diaryl disulfides, NH4I (1 mmol). The mixture was stirred at 135 °C for 12 hours, then cooled down to room temperature, diluted with 20 mL ethyl acetate and washed with 10 mL H2O. The aqueous layer was extracted twice with ethyl acetate (5 mL) and the combined organic phase was dried over Na2SO4. After evaporation of the solvents the residue was purified by flash column chromatography (silica gel, PE/EtOAc=5:1) to afford the desired products 3.

Reference： [1]Guo, Tao [Synthetic Communications, 2017, vol. 47, # 22, p. 2053 - 2061]

64
[ 5335-87-5 ]
[ 4783-68-0 ]
2-(2-(4-methoxyphenylthio)phenoxy)pyridine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 12430 - 12438

65
[ 5335-87-5 ]
(1-(2,6-dimethylphenoxy)-4-methylpenta-2,3-dien-2-yl)-diphenylphosphine oxide [ No CAS ]
(3-((4-methoxyphenyl)thio)-4-methylpenta-1,3-dien-2-yl)diphenylphosphine oxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With dipotassium peroxodisulfate In 1-methyl-pyrrolidin-2-one; water at 80℃; for 12h; Inert atmosphere;	S,P-Bifunctionalized Butadienes 3; General Procedure General procedure: To a 15 mL round-bottom flask was added allenylphosphine oxide 1(0.2 mmol), disulfide 2 (0.3 mmol), K2S2O8 (0.6 mmol) and NMP/H2O(1:1 v:v, 2 mL), and the resulting mixture was stirred for 12 h at 80 °C. The mixture was then diluted with EtOAc and sequentially washedwith saturated NaHCO3 solution and brine. The organic layer was collected and concentrated. The residue was purified by column chromatography(EtOAc/PE) to afford product 3.
74%	With Eosin Y; 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 20℃; for 8h; Irradiation; Inert atmosphere; Green chemistry;

Reference： [1]Luo, Kai; Zhang, Ling; Wei, Kai; Yang, Wen-Chao; Wu, Lei [Synthesis, 2018, vol. 50, # 15, p. 2990 - 2998]
[2]Zhang, Ling; Zhu, Jie; Ma, Jing; Wu, Lei; Zhang, Wei-Hua [Organic Letters, 2017, vol. 19, # 23, p. 6308 - 6311]

66
[ 5335-87-5 ]
[ 491-30-5 ]
4-((4-methoxyphenyl)thio)isoquinolin-1(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With silver hexafluoroantimonate; In 1,2-dichloro-ethane; at 80℃; for 10h;High pressure;	At room temperature, isoquinoline-1 (2Eta)-one (10 mmol), bis(4-methoxyphenyl)disulfide (13 mmol), silver hexafluoroantimonate were sequentially added to a pressure-resistant reaction tube. (8 mmol) and dichloroethane (8 mL). The reaction mixture was then reacted at 80 C for 10 hours. The reaction was stopped, concentrated under reduced pressure to give a crude material, which was washed with a mixture of petroleum ether and ethyl acetate. 4-(4-Methoxyphenylthio)isoquinolin-1(2Eta)-one. Yield 95%;

Reference： [1]Journal of Organic Chemistry,2018,vol. 83,p. 9958 - 9967
[2]Patent: CN108822035,2018,A .Location in patent: Paragraph 0021; 0022; 0023

67
[ 5335-87-5 ]
[ 82827-09-6 ]
6-bromo-4-((4-methoxyphenyl)thio)isoquinolin-1(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With silver hexafluoroantimonate; In 1,2-dichloro-ethane; at 90℃; for 10h;High pressure;	6-Bromoisoquinoline-1 (2Eta)-one (12mm0l), bis(4-methoxyphenyl)disulfide (10mmol), hexafluorofluoride was sequentially added to the pressure resistant reaction tube at room temperature. Silver acid (10 mmol) and dichloroethene (6 mL) were applied. Then the reaction mixture is at 90 C Reaction for 10 hours. The reaction was stopped, concentrated under reduced pressure to give a crude material, which was washed with a mixture of petroleum ether and ethyl acetate. 4-(4-Methoxyphenylthio)-6-bromoisoquinoline-1 (2H)-one. Yield 95%;

Reference： [1]Journal of Organic Chemistry,2018,vol. 83,p. 9958 - 9967
[2]Patent: CN108822035,2018,A .Location in patent: Paragraph 0039; 0040; 0041

68
[ 5335-87-5 ]
[ 131002-09-0 ]
6-chloro-4-((4-methoxyphenyl)thio)isoquinolin-1(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With silver hexafluoroantimonate; In 1,2-dichloro-ethane; at 90.0℃; for 10.0h;High pressure;	6-chloroisoquinolin-1 (2Eta)-one (12mm0l), bis(4-methoxyphenyl)disulfide (10mmol), hexafluorofluoride was sequentially added to the pressure resistant reaction tube at room temperature. Place silver acid (10 mmol) and dichloroethene (6 mL). Then the reaction mixture is at 90 C Reaction for 10 hours. The reaction was quenched and concentrated under reduced pressure to give a crude material which was washed with a mixture of petroleum ether and ethyl acetate. Flash column chromatography gave the corresponding product 4-(4-methoxyphenylthio)-6-chloroisoquinolin-1 (2H)-one. Yield 87%;

Reference： [1]Journal of Organic Chemistry,2018,vol. 83,p. 9958 - 9967
[2]Patent: CN108822035,2018,A .Location in patent: Paragraph 0054; 0055; 0056

69
[ 24188-74-7 ]
[ 5335-87-5 ]
7-chloro-4-((4-methoxyphenyl)thio)isoquinolin-1(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With silver hexafluoroantimonate; In 1,2-dichloro-ethane; at 105.0℃; for 10h;High pressure;	7-chloroisoquinolin-1 (2Eta)-one (12 mmol), bis(4-methoxyphenyldisulfide (15 mmol), hexafluoroantimonic acid was sequentially added to a pressure-resistant reaction tube at room temperature. Silver (10 mmol) and dichloroethane (10 mL). The reaction mixture was then at 105 C. The reaction was carried out for 10 hours. The reaction was quenched and concentrated under reduced pressure to give a crude material which was washed with a mixture of petroleum ether and ethyl acetate. Fast column chromatography to obtain the corresponding product 4-(4-Methoxyphenylthio)-7-chloroisoquinolin-1 (2H)-one. Yield 90%;

Reference： [1]Journal of Organic Chemistry,2018,vol. 83,p. 9958 - 9967
[2]Patent: CN108822035,2018,A .Location in patent: Paragraph 0072; 0073; 0074

70
[ 694-85-9 ]
[ 5335-87-5 ]
5-((4-methoxyphenyl)thio)-1-methylpyridin-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With silver hexafluoroantimonate In 1,2-dichloro-ethane at 110℃; for 8h;

Reference： [1]Zhu, You-Quan; He, Jing-Li; Niu, Yun-Xia; Kang, Hui-Ying; Han, Ting-Feng; Li, Hao-Yu [Journal of Organic Chemistry, 2018, vol. 83, # 17, p. 9958 - 9967]

71
[ 5335-87-5 ]
[ 135-77-3 ]
1,2,4-trimethoxy-5-(4-methoxyphenylsulfanyl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With ammonium peroxydisulfate; [Ir(dF(CF₃)ppy)₂(dtbpy)]PF₆ In acetonitrile at 25℃; for 6h; Irradiation; Inert atmosphere;	General procedure for C-H sulfenylation General procedure: In a 5 mL snap vial with magnetic stirring bar, the arene (0.1 mmol, 1.0 equiv), the aryl disulfide(2.0 equiv), (NH4)2S2O8 (1.7 equiv) and (Ir[dF(CF3)ppy]2(dtbpy))PF6 (0.002 mmol, 0.02 equiv)were added. Dry CH3CN (2.0 mL) were added under N2 and the mixture was degassed by“pump-freeze-thaw” cycles (×3) via a syringe needle. This reaction mixture was irradiatedthrough the plane bottom side of the snap vial using a 455 nm LED under nitrogen at 25 °C. Thereaction progress was monitored by GC analysis. After 6 h to 24 h of irradiation, the reactionmixture was transferred to separating funnel, diluted with ethyl acetate and washed with 15 mLof water. The aqueous layer was washed three times (3 × 15 mL) with ethyl acetate. Thecombined organic phases were dried over MgSO4, filtered and concentrated in vacuum.Purification of the crude product was achieved by flash column chromatography using petrolether/ethyl acetate as eluent.

Reference： [1]Das, Amrita; Maity, Mitasree; Malcherek, Simon; König, Burkhard; Rehbein, Julia [Beilstein Journal of Organic Chemistry, 2018, vol. 14, p. 2520 - 2527]

72
[ 5335-87-5 ]
[ 74-86-2 ]
[ 132752-95-5 ]

Yield	Reaction Conditions	Operation in experiment
82%	With triphenylphosphine In acetonitrile at 60℃; for 48h; Inert atmosphere; Sealed tube; stereoselective reaction;	2.3. General procedure of 1,2-bis(arylthio)ethenes synthesis General procedure: Solid reagents, including diaryl disulfide (0.2 mmol), Ni-4 (0.006 mmol, 2.2 mg) and PPh3 (0.06 mmol, 15.7 mg) were added to as crew-capped test-tube. Then the test-tube was flushed with argon, and the C2H2-presaturated MeCN (1 mL) was added. The tube was immediately closed with a screw cap. The reaction was carried out at 60 °C for the indicated time. In order to test the recyclability of Ni-4, the solid was separated from the reaction mixture by centrifugation and was washed with 3×5mL MeCN. After washing, the catalyst was re-used. After completing the reaction, the solvent was evaporated on a rotary evaporator and the product was purified by flash chromatography on silica 60 (0.015-0.40 mm) with hexane/CH2Cl2 gradient elution. The3a, 3b, 3c, 3f, 3i products were identified according to the literature data [7].
	With bis(acetylacetonate)nickel(II); triphenylphosphine In acetonitrile at 60℃; for 48h; Inert atmosphere; Sealed tube;	6 2.1.1 General Synthetic Procedure for synthesis of (Z)-1,2-bis(arylthio)ethene (1) General procedure: Acetylene was bubbled through acetonitrile in a water-ice bath for 30min. The solid reagents including disulfide (0.2mmol), Ni(acac)2 (6×10-3 mmol, 0.0015g), and PPh3 (6×10-2 mmol, 0.0157g) were added into a screw-capped test tube. The test tube with the solid reagents was flushed with argon, and the presaturated MeCN (1ml) was added. The tube was immediately closed with a screw cap. The reaction was carried out at 60°C under stirring for 2 days. After completing the reaction, the solvent was evaporated on a rotary evaporator and the product was purified by flash chromatography on silica gel 60 (0.015-0.040mm) with hexane/CH2Cl2 gradient elution. After drying under vacuum, the pure products were obtained.

Reference： [1]Ananikov, Valentine P.; Degtyareva, Evgeniya S.; Erokhin, Kirill S. [Catalysis Communications, 2020, vol. 146]
[2]Degtyareva, Evgeniya S.; Erokhin, Kirill S.; Kashin, Alexey S.; Ananikov, Valentine P. [Applied Catalysis A: General, 2019, vol. 571, p. 170 - 179]

73
[ 874-14-6 ]
[ 5335-87-5 ]
5-[(4-methoxyphenyl)thio]-1,3-dimethylpyrimidine-2,4(1H,3H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With dipotassium peroxodisulfate; iodine; In acetonitrile; at 60℃;	General procedure: An 8 mL oven-dried scintillation vial equipped with a magnetic stir bar was charged with a mixture of 4-quinolone or uracil (0.50 mmol, 1.0 equiv), disulfide or thiol (0.75 mmol, 1.5 equiv), molecular iodine (I2) (128 mg, 0.50 mmol, 1.0 equiv), K2S2O8 (1.00-1.50 mmol, 2.0-3.0 equiv), and acetonitrile (CH3CN) (1 mL). The vial was capped, and the reaction mixture was stirred at 60 or 80 C for 12-16 h. Upon completion, saturated Na2S2O3 (5 mL) and distilled deionized H2O (10 mL) was added, and the mixture was extracted with ethyl acetate (3 x 25 mL). The combined organic layer was washed with saturated NaCl, dried over anhydrous Na2SO4, and concentrated in vacuo. The crude product was purified by SiO2 column chromatography to afford the desired thioether products.

Reference： [1]European Journal of Organic Chemistry,2019,vol. 2019,p. 2759 - 2766
[2]Tetrahedron,2019,vol. 75

74
[ 103-19-5 ]
[ 5335-87-5 ]
[ 83180-92-1 ]

Yield	Reaction Conditions	Operation in experiment
75%	With N-fluorobis(benzenesulfon)imide In 1,2-dichloro-ethane at 50℃; for 4h; Schlenk technique; Sealed tube;	General procedure: 25 mL Schlenk tube was charged with RSSR 1 (0.2 mmol), R'SSR' 1' (0.4 mmol), NFSI (0.02 mmol) and DCE (2.0 mL). The tube was sealed and the reaction was then stirred vigorously at 50 C for 4 h. After cooling to room temperature, the reaction mixture was then concentrated in vacuo, and the crude product was purified by flash chromatography on silica gel to yield the product 4 (isolated yields are based on 0.4 mmol of 4).
21%	With 1,3-Diiodo-5,5-dimethyl-2,4-imidazolidinedione In acetonitrile at 20℃; for 0.5h;

Reference： [1]Hu, Qingyue; Li, Zheng-Yi; Song, Mengjie; Sun, Xiaoqiang; Yang, Ke [Chinese Chemical Letters, 2022]
[2]Iida, Keisuke; Ishida, Shunsuke; Watanabe, Takamichi; Arai, Takayoshi [Journal of Organic Chemistry, 2019]

75
[ 696-63-9 ]
[ 2557-78-0 ]
[ 5335-87-5 ]
[ 14135-38-7 ]
1-(2-fluorophenyl)-2-(4-methoxyphenyl)disulfane [ No CAS ]

Reference： [1]Chemistry - An Asian Journal,2019,vol. 14,p. 2579 - 2583

76
[ 696-63-9 ]
[ 98-02-2 ]
[ 4437-20-1 ]
[ 5335-87-5 ]
2-(((4-methoxyphenyl)disulfaneyl)methyl)furan [ No CAS ]

Reference： [1]Chemistry - An Asian Journal,2019,vol. 14,p. 2579 - 2583

77
[ 696-63-9 ]
[ 112-55-0 ]
[ 2757-37-1 ]
[ 5335-87-5 ]
1-dodecyl-2-(4-methoxyphenyl)disulfane [ No CAS ]

Reference： [1]Chemistry - An Asian Journal,2019,vol. 14,p. 2579 - 2583

78
[ 2550-40-5 ]
[ 5335-87-5 ]
[ 735269-14-4 ]

Yield	Reaction Conditions	Operation in experiment
91%	With potassium <i>tert</i>-butylate In tetrahydrofuran at 60℃; for 8h;
67%	With N-fluorobis(benzenesulfon)imide In 1,2-dichloro-ethane at 50℃; for 4h; Schlenk technique; Sealed tube;	3. General procedure for the scope study General procedure: A 25 mL Schlenk tube was charged with RSSR 1 (0.2 mmol), R1SSR1 2 (0.4 mmol), NFSI (0.02 mmol) and DCE (2.0 mL). The tube was sealed and the reaction was then stirred vigorously at 50 C for 4 h. After cooling to room temperature, the reaction mixture was then concentrated in vacuo, and the crude product was purified by flash chromatography on silica gel to yield the product 3 (isolated yields are based on 0.4 mmol of 3).

Reference： [1]Xu, Yulong; Shi, Xiaonan; Wu, Lipeng [RSC Advances, 2019, vol. 9, # 41, p. 24025 - 24029]
[2]Hu, Qingyue; Li, Zheng-Yi; Song, Mengjie; Sun, Xiaoqiang; Yang, Ke [Chinese Chemical Letters, 2022]

79
[ 492-38-6 ]
[ 5335-87-5 ]
C₁₆H₁₄O₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With rhodium(III) chloride trihydrate; copper diacetate; tris(2,6-dimethoxyphenyl)phosphine In N,N-dimethyl-formamide at 120℃; for 6h; regioselective reaction;

Reference： [1]Liu, Can; Fang, Yi; Wang, Shun-Yi; Ji, Shun-Jun [ACS Catalysis, 2019, vol. 9, # 10, p. 8910 - 8915]

80
[ 5335-87-5 ]
[ 187344-92-9 ]
S-(4-methoxyphenyl) bis(3,5-dimethylphenyl)phosphinothioate [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2019,vol. 17,p. 9757 - 9765

81
[ 5335-87-5 ]
[ 116632-42-9 ]
3-methoxy-7-methylphenoxathiine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With copper(l) iodide; caesium carbonate; dimethyl sulfoxide at 120℃; for 9h; Inert atmosphere;	Synthesis of 3-chlorophenoxathiine (3a). General procedure: CuI (10 mol %) Was added at room temperature to a mixture of disulfide 1a (0.5 mmol) with o-chloro-iodobenzene 2a (0.6 mmol) and Cs2CO3 (1.8 mmol) in DMSO (5 mL). The reaction mixture was stirred at 120°C for 9 h under the atmosphere of nitrogen. Upon completion of the process, the solvent was distilled off, and the residue was purified by column chromatography on silica gel (ethyl acetate-petroleum ether = 1 : 30, v:v) to give the product 3a.

Reference： [1]Chao, Fei; Xu, Wen-Heng; Ren, Zhi-Lin; Wang, Long [Russian Journal of General Chemistry, 2019, vol. 89, # 12, p. 2558 - 2561]

82
[ 624-31-7 ]
[ 5335-87-5 ]
[ 6013-47-4 ]

Yield	Reaction Conditions	Operation in experiment
96%	With tetra(n-butyl)ammonium hydroxide In water; N,N-dimethyl-formamide at 80℃; for 0.0833333h; Microwave irradiation;
93%	With potassium carbonate In water at 100℃; for 2h; Green chemistry;	4.6 General Procedure for Synthesis of DiarylSulfides andSelenides Via C-S andC-SeCross-coupling Reactions Catalyzed byFe3O4SiO2/2-amino Pyridine-Pd(II) General procedure: A mixture of aryl halide (1mmol), diaryl disulfide ordiselenide (0.5mmol), K2CO3(1mmol) and Fe3O4SiO2-/2-amino pyridine-Pd(II) (0.8mol%) in H2O/PEG(1:1, 2mL) was stirred at 100°C for the time indicatedin Tables2 and 3. The reaction progress was followed byTLC (eluent:ether/ethyl acetate, 5:1). At the end of thereaction, the mixture was cooled to room temperature,ethyl acetate (10mL) was added and the catalyst wasseparated by an eternal magnet. The organic phase waswashed with water (2 × 10mL) and dried over anhydrousMgSO4.The solvent was evaporated and the resultingcrude material was purified by recrystallization fromether and ethyl acetate (5:1) to afford the pure product.

Reference： [1]Amiri Rudbari, Hadi; Landarani-Isfahani, Amir; Mirkhani, Valiollah; Moghadam, Majid; Mohammadpoor-Baltork, Iraj; Tangestaninejad, Shahram [RSC Advances, 2020, vol. 10, # 36, p. 21198 - 21205]
[2]Lu, Lu; Luo, Jia; Wang, Weiqi; Xu, Xiaoqing; Zhang, Jingzheng [Catalysis Letters, 2022]

83
[ 5335-87-5 ]
[ 118486-97-8 ]
[ 1381847-78-4 ]

Reference： [1]Journal of Organic Chemistry,2020,vol. 85,p. 11942 - 11951

84
[ 19501-58-7 ]
[ 5335-87-5 ]

Yield	Reaction Conditions	Operation in experiment
90%	With sulfur; oxygen; caesium carbonate In water; toluene at 100℃; for 12h; Sealed tube; Schlenk technique;	1 Preparation of 1,2-bis(4-methoxyphenyl) disulfide: Add 70mg (0.4mmol) of 4-methoxyphenylhydrazine hydrochloride, S8100mg (0.4mmol), 910mg (7eq.) of cesium carbonate, 1mL of water, and 1mL of toluene into a 25ml Shrek tube.After feeding, add magnets to the Shrek tube, replace the air in the Shrek tube with oxygen and seal the tube. The oxygen pressure is 0.1MPa. The sealed Shrek tube is placed in a 100°C oil bath for heating and stirring for 12 hours. After the reaction is over, extract and separate the liquid, and after the organic phase is dried,Use a rotary evaporator to distill under reduced pressure to remove the organic solvent to obtain a crude product.After separation and purification by column chromatography, 44 mg of the target compound 1,2-bis(4-methoxyphenyl)disulfide was obtained with a yield of 90%

Reference： [1]Current Patent Assignee: XINXIANG RUNYU NEW MATERIAL TECH - CN111892469, 2020, A Location in patent: Paragraph 0041-0044

85
[ 5335-87-5 ]
[ 149-30-4 ]
2-((4-methoxyphenyl)disulfanyl)benzo[d]thiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With palladium dichloride In dimethyl sulfoxide at 80℃; for 2h; Inert atmosphere; Schlenk technique;	6 Example 6: 2-(p-methoxyphenyldisulfanyl)benzo[d]thiazole A method for preparing the above-mentioned asymmetric disulfide compound is characterized in that the specific steps are as follows: Under nitrogen protection, add 83.7 mg of 2-mercaptobenzothiazole and 278.3 mg of di-4-methoxyphenyl disulfide into a 25 mL Schlenk tube Ether and 4.5mg of palladium dichloride, add 2.0mL DMSO under nitrogen, heat to 80C, and react for 2h. After cooling, it was poured into 5mL water, the product was extracted with 30mL dichloromethane, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was removed with a rotary evaporator to obtain the crude product; the crude product was subjected to column chromatography (PE: ΕΑ = 500:1 ) Purification to obtain 131.1 mg of light yellow product, melting point: 57-58C, yield 86%.
86%	With palladium dichloride In dimethyl sulfoxide at 80℃; for 2h; Inert atmosphere;

Reference： [1]Current Patent Assignee: SHANGHAI UNIVERSITY - CN112047902, 2020, A Location in patent: Paragraph 0048-0050
[2]Guo, Jimin; Zha, Jianjian; Zhang, Tao; Ding, Chang-Hua; Tan, Qitao; Xu, Bin [Organic Letters, 2021, vol. 23, # 8, p. 3167 - 3172]

86
[ 5335-87-5 ]
[ 3282-32-4 ]
2-chloro-2-((4-methoxyphenyl)thio)-1-phenylethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With (Dichloroiodo)benzene In acetonitrile at 25℃; for 1h;	13 Example 13 Dichloroiodobenzene (0.11 mmol), bis 4-methoxyphenyl disulfide (0.11 mmol) were dissolved in acetonitrile (2.0 mL), and then phenylcarbonyl diazonium (0.2 mmol) diluted in acetonitrile (1 mL) ) Slowly add dropwise to the reaction system. The reaction system is at room temperature (25°C). After the addition is complete, stir for 1.0 h, and remove the solvent under reduced pressure to obtain a crude product, the structure of which is shown in formula (4-6). The crude product was subjected to column chromatography (ethyl acetate: petroleum ether = 1:30 to 1:10) to obtain a pure product. The yield was 90%.
86%	Stage #1: 4,4'-dimethoxyphenyl disulfide With (Dichloroiodo)benzene In dichloromethane at 20℃; Stage #2: 2-diazo-acetophenone In dichloromethane at 20℃; for 1h;

Reference： [1]Current Patent Assignee: PINGDINGSHAN UNIVERSITY - CN112430202, 2021, A Location in patent: Paragraph 0069-0071
[2]Li, Jiuling; Li, Bin; Chen, Juan; Jia, Xinyu; Wang, Min; Hao, Chengjun; Zheng, Xinhua; Dai, Hongmei; Hu, Wenhao [Organic and Biomolecular Chemistry, 2021, vol. 19, # 37, p. 8030 - 8034]

87
[ 719-98-2 ]
[ 768-56-9 ]
[ 5335-87-5 ]
(4-methoxyphenyl)(4-phenyl-1-((trifluoromethyl)thio)butan-2-yl)sulfane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With dipotassium hydrogenphosphate; (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; In dimethyl sulfoxide; at 20.0℃; for 24.0h;Inert atmosphere; Irradiation;	General procedure: Under argon, 4CzIPN (2 mol %) and <strong>[719-98-2]N-(trifluoromethylthio)phthalimide</strong> (3, 1.5 equiv),1a (0.2 mmol, 1 equiv), 2a (0.2 mmol, 1 equiv), and K2HPO4 (10 mol %) were dissolvedin dried DMSO (2 mL) at room temperature. After that, the tube was exposed to 10 Wblue LEDs and the mixture was stirred at room temperature for about 24 h until thereaction was completed as monitored by TLC analysis. Then, the reaction solution waspoured into 10 mL of water. The aqueous phase was extracted with EA (3 × 15 mL). Thecombined organic phases were washed with 15 mL of water and 15 mL of brine. Afterdrying over Na2SO4 and removal of the solvent in vacuo, the crude products were directlypurified by flash chromatography on silica gel to give the desired product.

Reference： [1]Beilstein Journal of Organic Chemistry,2021,vol. 17,p. 551 - 557

88
[ 5335-87-5 ]
[ 629-19-6 ]
1-(4-methoxyphenyl)-2-propyldisulfane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With N-fluorobis(benzenesulfon)imide In 1,2-dichloro-ethane at 50℃; for 4h; Schlenk technique; Sealed tube;	3. General procedure for the scope study General procedure: A 25 mL Schlenk tube was charged with RSSR 1 (0.2 mmol), R1SSR1 2 (0.4 mmol), NFSI (0.02 mmol) and DCE (2.0 mL). The tube was sealed and the reaction was then stirred vigorously at 50 C for 4 h. After cooling to room temperature, the reaction mixture was then concentrated in vacuo, and the crude product was purified by flash chromatography on silica gel to yield the product 3 (isolated yields are based on 0.4 mmol of 3).

Reference： [1]Song, Mengjie; Hu, Qingyue; Li, Zheng-Yi; Sun, Xiaoqiang; Yang, Ke [Chinese Chemical Letters, 2022, vol. 33, # 9, p. 4269 - 4272]

Type	HazMat fee for 500 gram (Estimated)
Excepted Quantity	USD 0.00
Limited Quantity	USD 15-60
Inaccessible (Haz class 6.1), Domestic	USD 80+
Inaccessible (Haz class 6.1), International	USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic	USD 100+
Accessible (Haz class 3, 4, 5 or 8), International	USD 200+

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CAS No. :	5335-87-5	MDL No. :	MFCD00041358
Formula :	C₁₄H₁₄O₂S₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PZQGLCGLPMWYBT-UHFFFAOYSA-N
M.W :	278.39	Pubchem ID :	79258
Synonyms :

Signal Word:	Danger	Class:	9
Precautionary Statements:	P273-P280-P305+P351+P338-P501	UN#:	3077
Hazard Statements:	H318-H410	Packing Group:	Ⅲ
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

[ CAS No. 5335-87-5 ] {[proInfo.proName]}

Quality Control of [ 5335-87-5 ]

Related Doc. of [ 5335-87-5 ]

Product Details of [ 5335-87-5 ]

Safety of [ 5335-87-5 ]

Application In Synthesis of [ 5335-87-5 ]

[ 5335-87-5 ] Synthesis Path-Downstream 1~88

Related Functional Groups of
[ 5335-87-5 ]

Aryls

Ethers

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

[ CAS No. 5335-87-5 ] {[proInfo.proName]}

Quality Control of [ 5335-87-5 ]

Related Doc. of [ 5335-87-5 ]

Product Details of [ 5335-87-5 ]

Safety of [ 5335-87-5 ]

Application In Synthesis of [ 5335-87-5 ]

[ 5335-87-5 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 5335-87-5 ]

Aryls

Ethers

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 5335-87-5 ]