Select Region or Location
Americas
  • Argentina
  • Brazil
  • Canada
  • Mexico
  • United States
  • Other Americas
Europe
  • Austria
  • Belgium
  • Bulgaria
  • Croatia/Hrvatska
  • Cyprus
  • Czech Republic
  • Denmark
  • Estonia
  • Finland
  • France
  • Germany
  • Greece
  • Hungary
  • Ireland
  • Italy
  • Latvia
  • Liechtenstein
  • Lithuania
  • Luxembourg
  • Malta
  • Netherlands
  • Norway
  • Poland
  • Portugal
  • Romania
  • Slovak Republic
  • Slovenia
  • Spain
  • Sweden
  • Switzerland
  • Turkey
  • United Kingdom
  • Other Europe
Asia Pacific
  • Australia
  • China
  • India
  • Indonesia
  • Japan
  • Korea, Republic of
  • Malaysia
  • New Zealand
  • Philippines
  • Singapore
  • Thailand
  • Vietnam
  • Other Asia Pacific
Africa And Middle East
  • Egypt
  • Israel
  • Other Africa And Middle East
USD
Home Cart Sign in  
Chemical Structure| 10496-18-1 Chemical Structure| 10496-18-1

Structure of Decyl disulfide
CAS No.: 10496-18-1

Chemical Structure| 10496-18-1

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only! Not for Human Use. We Do Not Sell to Patients.

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

DE Stock

US Stock

Asia Stock

Global Stock

In Stock
{[ item.pr_size ]}{[ size_append_text(item.pr_size, proInfo.prAm, 'list') ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

  • {[ item.pr_size ]}
    {[ size_append_text(item.pr_size, proInfo.prAm, 'list') ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 10496-18-1 ]

CAS No. :10496-18-1
Formula : C20H42S2
M.W : 346.68
SMILES Code : CCCCCCCCCCSSCCCCCCCCCC
English Name :1,2-Didecyldisulfane
MDL No. :MFCD00039859
InChI Key :IDJPKRIELSFBPE-UHFFFAOYSA-N
Pubchem ID :139170

Safety of [ 10496-18-1 ]

Application In Synthesis of [ 10496-18-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 10496-18-1 ]

[ 10496-18-1 ] Synthesis Path-Downstream   1~13

  • 1
  • [ 143-10-2 ]
  • [ 10496-18-1 ]
YieldReaction ConditionsOperation in experiment
100% With aluminum oxide; sodium iodate In hexane at 20℃; for 1.5h;
100% With (S)-tetrahydrotellurophen-3-amine hydrochloride; dihydrogen peroxide In dichloromethane at 25℃; Flow reactor;
100% With tert.-butylhydroperoxide In chloroform at 27℃; for 1h; 2-3 bond reaction in low molecular weight organic compounds Using decanethiol as a substrate, hydrogen peroxide (H2O2) or t-butyl hydroperoxide (tBuOOH) as an oxidant, as shown in Table 1, and ethanol (EtOH), acetonitrile (CH3CN), ethyl acetate (EtOAc), toluene, chloroform (CHCl3), or dichloromethane (CH2Cl2) as a solvent, a disulfide bond reaction catalyzed by a resin-supported cyclic tellurium compound was carried out by the method described below. The choice of whether to use H2O2or tBuOOH as the oxidant was determined from the viewpoint of solubility in the solvent.Decanethiol contains one thiol group per molecule. In this reaction, the two thiol groups in two decanethiol molecules are converted into disulfide bonds, forming a decanethiol dimer linked by an intermolecular disulfide bond.[0037]A resin-supported cyclic tellurium compound (0.27 μmol) and 1 μL of solvent were added to a column-type filter vessel for solid-phase synthesis. After allowing the resin to swell for at least 1 hour, the solvent was removed by suction filtration. The resin was then washed three times with 500 μL of solvent.To this was added solvent (1 μL), decanethiol (54 μmol, 9.4 mg), and HO(59μmol, 5.2 μL) or tBuOOH (59 μmol, 8.1 μL). The disulfide bond formation reaction was carried out by shaking and stirring at 27°C for 1 hour.The solution containing the dissolved reaction product was recovered by suction filtration and concentrated using an evaporator.
98% With air In hexane at 30℃; for 2.5h;
96% With aluminum oxide; dimethyl sulfoxide at 70℃; for 2.5h;
96% With potassium carbonate; copper dichloride In methanol
94% With calcium hypochlorite; Montmorillonite K10 In hexane at 20℃; for 0.25h;
91% With 2-((3-(triethoxysilyl)propyl)thio)ethane-1-sulfonyl fluoride; sodium hydroxide In acetonitrile at 20℃; for 12h;
90% With calcium hypochlorite; water; silica gel In hexane at 20℃; for 0.5h;
90% With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione In chloroform at 20℃; for 2h; Inert atmosphere;
89% With dimethyl sulfoxide for 19h; Heating;
85% With sodium hydroxide; cobalt phthalocyaninetetrasulphonamide; oxygen In water at 20℃; for 0.583333h;
85% With oxygen In N,N-dimethyl-formamide at 23℃; for 0.75h; Sonication; Green chemistry;
85% With phosphorus; potassium hydroxide In dimethyl sulfoxide; toluene at 20℃; for 4h;
With bromine Ambient temperature; Yield given;
With manganese(IV) oxide; molecular sieve In hexane for 1h; Heating; Yield given;
With cobalt phthalocyaninetetrasulfonate (CoPcTsNa4); oxygen In water at 35℃; var. cationic latexes-catalyst systems; var. inhibitors; var. reaction conditions; activation energy;
With chlorine dioxide In tetrachloromethane at 40℃;
With C222H156Fe4N24(8+)*8C2F6NO4S2(1-) In [D3]acetonitrile at 50℃; for 11.5h; Sealed tube;
58 % With silica gel; potassium hexacyanoferrate(III) at 80℃; Milling;
100 % With tert.-butylhydroperoxide In chloroform at 27℃; chemoselective reaction;
76 % With N-(benzyloxy)-N-(pivaloyloxy)-4-(trifluoromethyl)benzamide In acetonitrile at 20℃; Inert atmosphere;

References: [1]Hirano, Masao; Yakabe, Sigetaka; Ando, Ken-Ichiro; Morimoto, Takashi [Journal of Chemical Research - Part S, 1998, # 12, p. 816 - 817].
[2]Arai, Kenta; Osaka, Yuui; Haneda, Masahiro; Sato, Yuumi [Catalysis science and technology, 2019, vol. 9, # 14, p. 3647 - 3655].
[3]Current Patent Assignee: TOKAI UNIVERSITY - JP2025/109012, 2025, A Location in patent: Paragraph 0036-0040.
[4]Hirano, Masao; Monobe, Hiroyuki; Yakabe, Sigetaka; Morimoto, Takashi [Journal of Chemical Research - Part S, 1999, # 6, p. 374 - 375].
[5]Hirano, Masao; Yakabe, Sigetaka; Monobe, Hiroyuki; Morimoto, Takashi [Journal of Chemical Research - Part S, 1998, # 8, p. 472 - 473].
[6]Vaquer, Andrea F.; Frongia, Angelo; Secci, Francesco; Tuveri, Enrica [RSC Advances, 2015, vol. 5, # 117, p. 96695 - 96704].
[7]Hirano, Masao; Yakabe, Shigetaka; Fukami, Masataka; Morimoto, Takashi [Synthetic Communications, 1997, vol. 27, # 16, p. 2783 - 2788].
[8]Hou, Jiaman; Wang, Minlong; Qin, Xinshu; Peng, Ruoqing; Li, Hengzhao; Zhang, Xiaohe; Zhang, Xiaoxu; Han, Minhui; An, Jie [Organic Letters, 2025, vol. 27, # 27, p. 7434 - 7438].
[9]Hirano, Masao; Yakabe, Shigetaka; Uraoka, Nobuteru; Morimoto, Takashi [Organic Preparations and Procedures International, 1998, vol. 30, # 3, p. 360 - 363].
[10]Howard, Joseph L.; Schotten, Christiane; Alston, Stephen T.; Browne, Duncan L. [Chemical Communications, 2016, vol. 52, # 54, p. 8448 - 8451].
[11]Oyaizu, Kenichi; Iwasaki, Tomokazu; Tsukahara, Yoshiaki; Tsuchida, Eishun [Macromolecules, 2004, vol. 37, # 4, p. 1257 - 1270].
[12]Venkateshwar Rao; Narasimha Rao; Jain, Suman L.; Sain, Bir [Synthetic Communications, 2002, vol. 32, # 8, p. 1151 - 1157].
[13]Chauhan, Deepak K.; Patnam, Padma L.; Ganguly, Sudip K.; Jain, Suman L. [RSC Advances, 2016, vol. 6, # 57, p. 51983 - 51988].
[14]Huangfu, Xinlei; Wang, Yueqiao; Lu, Guozhang; Cao, Yinwei; Tang, Guo; Zhao, Yufen [Green Chemistry, 2020, vol. 22, # 16, p. 5303 - 5309].
[15]Wu, Xiaoming; Rieke, Reuben D.; Zhu, Lishan [Synthetic Communications, 1996, vol. 26, # 1, p. 191 - 196].
[16]Hirano, Masao; Yakabe, Sigetaka; Chikamori, Hideki; Clark, James H.; Morimoto, Takashi [Journal of Chemical Research - Part S, 1998, # 6, p. 310 - 311].
[17]Hassanein, M.; Ford, Warren T. [Journal of Organic Chemistry, 1989, vol. 54, # 13, p. 3106 - 3113].
[18]Yakupov; Shereshovets; Imashev; Ismagilov [Russian Chemical Bulletin, 2001, vol. 50, # 12, p. 2352 - 2355].
[19]Da Camara, Bryce; Dietz, Philip C.; Chalek, Kevin R.; Mueller, Leonard J.; Hooley, Richard J. [Chemical Communications, 2020, vol. 56, # 91, p. 14263 - 14266].
[20]Grundke, Caroline; Groß, Jonathan; Vierengel, Nina; Sirleaf, Jason; Schmitz, Matthias; Krieger, Leonie; Opatz, Till [Organic and Biomolecular Chemistry, 2022, vol. 21, # 3, p. 644 - 650].
[21]Nishizawa, Yuya; Satoh, Yuri; Kanie, Osamu; Arai, Kenta [New Journal of Chemistry, 2023, vol. 47, # 40, p. 18537 - 18546].
[22]Xu, Xiaobo; Yan, Leyu; Huang, Weijie; Wang, Yanping; Wang, Mengya; Feng, Liming; Wang, Panpan; Wang, Shengqiang [RSC Advances, 2024, vol. 14, # 25, p. 17780 - 17784].
  • 2
  • [ CAS Unavailable ]
  • [ 10496-18-1 ]
YieldReaction ConditionsOperation in experiment
87% With samarium; iodine In tetrahydrofuran for 4h; Ambient temperature;
85% With samarium; ammonium chloride In tetrahydrofuran; water at 20℃; for 4h;
85% With samarium; chloro-trimethyl-silane; water In tetrahydrofuran at 20℃; for 5h;
85% With samarium In water at 90℃; for 4h;
76% In tetrahydrofuran; water at 20℃; for 4h;
74% With samarium diiodide In tetrahydrofuran for 0.5h; Ambient temperature;
With water; iodine In ethanol Yield given;
With samarium diiodide In tetrahydrofuran

  • 3
  • [ 872-31-1 ]
  • [ 10496-18-1 ]
  • [ 92372-03-7 ]
YieldReaction ConditionsOperation in experiment
75% Stage #1: 3-Bromothiophene With n-butyllithium In tetrahydrofuran; hexane at -40 - 20℃; Stage #2: didecyl disulfide In tetrahydrofuran; hexane at 20℃; for 2h;
  • 4
  • [ 928852-82-8 ]
  • [ 10496-18-1 ]
YieldReaction ConditionsOperation in experiment
63% With water In dichloromethane at 20℃; for 120h;
  • 5
  • [ 2050-77-3 ]
  • [ 10496-18-1 ]
YieldReaction ConditionsOperation in experiment
94% With sodium sulfide trihydrate; hexachloroethane at 20℃; for 1.5h; General Procedure General procedure: Na2S·3H2O (0.291 g, 2.2 mmol) was addedto a magnetically stirred solution of an alkyl halide (2 mmol) and C2Cl6 or CCl4 (1.5 mmol) in PEG-200 (2 mL) at r.t. The stirring was continued until the starting halide was completely consumed (30-150 min). Next, the reaction mixture was diluted with H2O (1 mL) and extracted with EtOAc-hexane (1:1;4 × 2 mL). The organic extracts were combined, concentrated and purified by chromatography on silica gel. The desired disulfides were produced in excellent yields (Table 1).
91% With sodium carbonate; sulfur; thiourea In water at 40℃; for 12h; Green chemistry;
91% With Sodium thiosulfate pentahydrate; water; dimethyl sulfoxide at 60 - 70℃; for 7h;
90% With manganese(IV) oxide; sodium dodecyl-sulfate; sodium hydrogencarbonate; thiourea In water at 80℃; for 4h; Micellar solution;
90% With water; oxygen; sodium hydrogencarbonate; thiourea at 80 - 90℃; for 2h; Green chemistry; 2.2. General procedure for conversion of alkyl halides to disulfidesin PEG 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 alkyl halide (2.0 mmol), thiourea (2.2 mmol), H2O(0.1 mL), and NaHCO3 (3.0 mmol) in PEG 200 (1 mL) and themixture was stirred magnetically in an oil bath at 80-90 °C. Thestirring was continued under such conditions up to 2 h after thecomplete consumption of the starting halide. Next, the mixturewas diluted with water (0.5 mL) and extracted with 1:2 n-hexane/EtOAc (3 x 1 mL). The organic layers were decanted, combined,and concentrated to yield the crude product, which wasfurther purified by silica gel chromatography, using n-hexane aseluent.
90% With carbon disulfide; potassium cyanide In N,N-dimethyl-formamide at 20 - 60℃; for 1.75h; Representative procedure for the synthesis of 1,2-dibenzyldisulfane from benzyl chloride General procedure: CS2 (1.3 mmol, 0.07 mL) was added to a stirred solution of KCN (1.1 mmol, 0.07 g) in DMF (1 mL) at room temperature. After 15 min, benzyl chloride (1.0 mmol, 0.11 mL) was added and the reaction mixture stirred at 60 °C. Upon reaction completion (TLC, 45 min), the mixture was cooled to room temperature, diluted with H2O (1 mL), and extracted with n-hexane/ethyl acetate (1:1, 4 × 1 mL). The combined organic extracts were dried, evaporated at 90 °C and the residue purified by silica gel column chromatography using n-hexane as eluent to give the pure dibenzyldisulfane as a white crystalline powder in 87% (0.107 g) yield.
87% With dimethyl sulfoxide; thiourea; 1,1,1,3,3,3-hexamethyl-disilazane In water at 50℃; for 10h; General procedure General procedure: An alkyl halide (2 mmol) and HMDS (3 mmol) were addedto a solution of thiourea (2.2 mmol) in wet DMSO (2 mLDMSO + 0.05 mL H2O). The mixture was stirred magneticallyat 50 °C for 10-24 h. Then, the mixture was dilutedwith water (2 mL) and extracted with 1:1 EtOAc/hexane(3 × 2 mL). The upper layers were decanted, combined,and concentrated. The crude product was purified by silicagel chromatography using low-boiling petroleum ether aseluent to provide the desired disulfide in high yield.
85% With manganese(IV) oxide; sodium carbonate; thiourea In water at 30 - 35℃; for 12h;

  • 6
  • [ 10496-18-1 ]
  • [ 68259-13-2 ]
  • [ 1309877-85-7 ]
YieldReaction ConditionsOperation in experiment
1: 36 %Chromat. 2: 26 %Chromat. With water; Selectfluor In acetonitrile at 20℃; for 0.333333h; A representative experimental procedure to prepare thiosulfonates from disulfides General procedure: To a stirred solution of p-tolyl disulfide (246.3 mg, 1.0 mmol) in acetonitrile (2.0 ml) and water (0.2 ml) was added Selectfluor (885.5 mg, 2.5 mmol) at room temperature for 20 min, and the resulting mixture was stirred. The reaction was monitored by thin layer chromatography (TLC). After the disulfide disappeared from the TLC, water (5 ml) was added and the resulting mixture was extracted with ethyl acetate (15 ml × 3). The extract was washed with brine, dried over anhydrous magnesium sulfate, and evaporated. Chromatography on silica gel gave thiosulfonate (259.3 mg, 93%) as colorless crystals.
1: 36 %Chromat. 2: 26 %Chromat. With Selectfluor In water; acetonitrile at 20℃; for 0.333333h; Representative experimental procedure to prepare thiosulfonates from disulfides General procedure: Representative experimental procedure to prepare thiosulfonates from disulfides To a stirred solution of p-tolyl disulfide (1b) (246.3 mg, 1.0 mmol) in acetonitrile (2.0 mL) and water (0.2 mL), Selectfluor (885.5 mg, 2.5 mmol) was added at room temperature for over 20 min, and the resulting mixture was stirred. The reaction was monitored via thin layer chromatography (TLC). After the disulfide disappeared from the TLC, water (5 mL) was added, and the resulting mixture was extracted with ethyl acetate (15 mL*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 corresponding thiosulfonate (2b) (259.3 mg, 93%) as colorless crystals.
  • 7
  • [ 10496-18-1 ]
  • [ 68259-13-2 ]
YieldReaction ConditionsOperation in experiment
91% 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.
91% 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
  • 8
  • [ 10496-18-1 ]
  • [ 61652-81-1 ]
YieldReaction ConditionsOperation in experiment
91% With N-chloro-succinimide In water; acetonitrile at 20℃; for 1h; 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.
  • 9
  • [ 10496-18-1 ]
  • [ 1582739-60-3 ]
YieldReaction ConditionsOperation in experiment
100% With NBS In lithium hydroxide monohydrate; acetonitrile at 20℃; for 2.7h; 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.
79% With sodium hypochlorite pentahydrate; glacial acetic acid; sodium bromide for 0.166667h; 7 General procedure: In an eggplant type flask, sodium hypochlorite pentahydrate1.06 g (6.4 mmol),0.82 g (8.0 mmol) of sodium bromide, and 8 mL of acetic acid,And the mixture was stirred under warming for 20 minutes. after that,0.246 g (1.0 mmol) of the raw material di-p-tolyl disulfide was added and reacted for 80 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, dried, After that, the solvent was distilled off,0.473 g (1.7 mmol, yield: 85%) of p-tolylsulfonyl bromide as a reaction product was obtained.As bis (p-chlorophenyl) disulfideThe oxidation reaction was carried out in the same manner as in Example 3 except that 0.287 g (1.0 mmol) was used. The reaction time was 55 minutes.After completion of the reaction, the obtained reaction mixture was treated in the same manner as in Example 4 to obtain 0.3748 g (1.5 mmol, yield 73%) of p-chlorobenzenesulfonyl bromide as a reaction product.Using each disulfide shown in Table 1 as a reaction substrate, oxidation reaction was carried out in the same manner as in Example 5, and the corresponding sulfonyl bromide was obtained in the same manner as in Example 5.
79% With sodium hypochlorite pentahydrate; sodium bromide In glacial acetic acid at 20℃; for 0.166667h; Standard Procedure for the Synthesis of Sulfonyl Bromides 4 from Disulfides 1 or Thiols 2 (Tables 8 and 9) General procedure: To a solution of NaBr (823 mg, 8.0 mmol) in acetic acid (7 mL), NaOCl·5H2O (1.07 g, 6.5 mmol) was added under stirring, and the resulting mixture was stirred at room temperature for another 30 min. A solution of disulfide (1) or thiol (2) (1.0 mmol) in AcOH (1 mL) was then added to the mixture under stirring. The reaction was monitored by TLC and stirring was continued until the starting material disappeared. H2O (50 mL) was added to the reaction mixture, which was then extracted with chloroform (3 × 5 mL). The combined extract was dried (anhyd MgSO4) and evaporated to obtain the corresponding sulfonyl bromide 4. The product was analyzed without further purification.
  • 10
  • [ 10496-18-1 ]
  • [ 1309877-85-7 ]
YieldReaction ConditionsOperation in experiment
89% With Oxone; potassium bromide In water; acetonitrile at 20℃; for 0.466667h; 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).
  • 11
  • [ 2050-77-3 ]
  • [ 62-56-6 ]
  • [ 10496-18-1 ]
YieldReaction ConditionsOperation in experiment
86% With tetrachloromethane; water; triethylamine In glycerol at 50℃; for 12h; General procedure: A mixture of an alkyl halide (2 mmol), thiourea (2.5 mmol),Et3N (3.5 mmol) and CCl4 (2 mmol) in wet glycerol (2 mLglycerol + 0.1 mL H2O) was stirred magnetically at 50 °Cfor 12-24 h. Then H2O (1 mL) was added to the reactionmixture and the reaction was extracted with EtOAc(3 × 2 mL). The organic layers were decanted, combined,dried over Na2SO4, and concentrated to yield the crudedisulfide, which was further purified by silica gel chromatographyusing low-boiling petroleum ether as eluent toprovide the desired disulfides in good to excellent yields
72% With sodium carbonate In water; acetonitrile at 80℃; for 3h; General Procedure for the Synthesis of Alkyl Disulfides General procedure: A mixture of an alkyl halide or alkyl tosylates 1 (2 mmol), thiourea (2.2 mmol),graphene oxide (60 wt%), and Na2CO3 (3 mmol) in wet acetonitrile (2 mL CH3CN +0.2 mL H2O) was stirred at 80 C for 3-12 h. The progress of reaction was monitored byTLC using n-hexane. The reaction mixture was then cooled to room temperature and thegraphene oxidewas separated by simple filtration. The filtratewas evaporated under reducedpressure to get the crude product, which was further purified by silica gel chromatographyusing n-hexane as eluent to give disulfide 2 (Table 2). Characterization details of knownproducts, and graphene oxide are provided in the Supplemental Materials.
  • 12
  • [ 10496-18-1 ]
  • [ 55883-63-1 ]
YieldReaction ConditionsOperation in experiment
With chlorine In Petroleum ether at -10℃; for 1h; 4.1 Step (1), Synthesis of n-decylthiochloride With a stirring rod, a condenser, a thermometer,52g of n-decyl disulfide was added to the bubbler and exhaust gas absorption 250ml four-necked flask.100g of petroleum ether, cooling to -10 ° C,Slowly pass 12g of chlorine gas and keep the reaction for 1h.A petroleum ether solution of the intermediate n-decylthiochloride is obtained.
  • 13
  • [ 143-10-2 ]
  • [ 10496-18-1 ]
  • [ 116139-32-3 ]
YieldReaction ConditionsOperation in experiment
1: 91.7 %Spectr. 2: 8.3 %Spectr. With sulphur; potassium carbonate In neat (no solvent) at 30 - 90℃; General procedure fortheoxidative coupling reaction General procedure: The general formula of oxidative coupling reaction was showed in Scheme2. RSH (the nine kinds of alkyl mercaptans were denoted as 1a~1i, 0.3 mol or 0.21 mol), sublimed sulfur (0.1 mol), quantitative phase transfer agent (PTA) and potassium salt (KA, A=anion) catalyst were successively added into a 100 mL single-necked round bottom fask equipped with stir bar and condenser, stirred and started timing. The initial oil bath temperature was 30 °C and it was heated to 90 °C at a heating rate of 3.6 °C/min. The release of H2S gas was monitored by draining saturated H2S aqueous solutions [35]. The reaction induction period was the time from the beginning of the timing to the discharge of the frst drop of saturated aqueous solution. The reaction ended when the saturated H2S aqueous solution was no longer discharged. After the reactants were cooled to room temperature, the product composition was analyzed by GC on Scion 436 (Agilent). The chromatographic column was Scion-WaxMS capillary column (SC32434, 30 m*0.32 mm ID*0.50 μm df, VFWAXms). Considering the thermal unstable byproduct dialkyl polysulfde (R2Sn, n>2), 1 H NMR determination was employed for R2S2 (2a~2i, target product), R2S3 (3a~3i), and R2S4 (4a~4i) in order to assure the accuracy of analysis of product distribution by GC. 1 H NMR determination was carried out on Ascend 400 (Bruker, 400 MHz) with deuterium chloroform (99.8% atomic D, containing 0.03% V/V tetramethylsilane and silver foil stabilizer) as solvent and TMS as internal standard.
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 10496-18-1 ]

Aliphatic Chain Hydrocarbons

Chemical Structure| 2757-37-1

A134581 [2757-37-1]

1,2-Didodecyldisulfane

Similarity: 1.00

Chemical Structure| 2885-00-9

A272296 [2885-00-9]

Octadecane-1-thiol

Similarity: 0.60

Chemical Structure| 56-17-7

A210400 [56-17-7]

2,2'-Disulfanediyldiethanamine dihydrochloride

Similarity: 0.50

Chemical Structure| 1119-62-6

A161411 [1119-62-6]

3,3-Dithiodipropionic Acid

Similarity: 0.50

Sulfides

Chemical Structure| 2757-37-1

A134581 [2757-37-1]

1,2-Didodecyldisulfane

Similarity: 1.00

Chemical Structure| 56-17-7

A210400 [56-17-7]

2,2'-Disulfanediyldiethanamine dihydrochloride

Similarity: 0.50

Chemical Structure| 1119-62-6

A161411 [1119-62-6]

3,3-Dithiodipropionic Acid

Similarity: 0.50