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[ CAS No. 3446-89-7 ]

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Chemical Structure| 3446-89-7
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CAS No. :3446-89-7 MDL No. :MFCD00006948
Formula : C8H8OS Boiling Point : 86-90°C at 1 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :152.21 g/mol Pubchem ID :76985
Synonyms :

Safety of [ 3446-89-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 3446-89-7 ]

  • Upstream synthesis route of [ 3446-89-7 ]
  • Downstream synthetic route of [ 3446-89-7 ]

[ 3446-89-7 ] Synthesis Path-Upstream   1~38

  • 1
  • [ 37794-15-3 ]
  • [ 3446-89-7 ]
YieldReaction ConditionsOperation in experiment
92% With silica bromide In dichloromethane at 20℃; for 0.166667 h; Inert atmosphere General procedure: In a typical procedure, diphenyl sulfoxide (2.2 g, 0.01 mol) and brominated silica (18.18 g, 40 mmole Br/g silica) are mixed in an aprotic solvent, e.g. dichloromethane (2 mL) or carbon tetrachloride, at room temperature with exclusion of atmospheric moisture, for 5 min. Diphenyl sulfide is isolated in pure state by simple filtration and evaporation of the solvent (1.84, 99percent).
90% With tantalum pentachloride; sodium iodide In acetonitrile at 20℃; for 0.0833333 h; General procedure: In a 10 mL round-bottom flask, to a solution of diphenylsulfoxide (202 mg, 1.0mmol) in CH3CN (4 mL), tantalum (IV) chloride (179 mg, 0.5 mmol) and sodium iodide (300 mg, 2.0 mmol) were added at room temperature. The mixture turned dark brown almost immediately and the progress of the reaction was followed by TLC. After completion of the reaction (3 min), the reaction mixture was diluted with water and then extracted with ethyl acetate. The combined organic extracts were washed successively with 10percent aq Na2S2O3 and H2O. The organic layer was separated and dried over anhydrous Na2SO4 and concentrated under reduced pressure. The resulting crude product was purified through silicagel column chromatography (hexane:ethyl acetate = 2:1) to afford diphenylsulfide (88 mg, 95percent).
89% With hafnium tetrachloride; zinc In acetonitrile at 20℃; for 3 h; General procedure: Diphenylsulfoxide (101 mg, 0.5 mmol) and hafnium(IV) chloride (320 mg, 1.0 mmol) were mixed in CH3CN (5 mL) and zinc powder (131 mg, 2.0 mmol) was then added to this solution. The whole mixture was stirred for 3 h at room temperature and the progress of the reaction was followed by TLC. On completion, the solvent was removed under reduced pressure and the residue was extracted successively with ethyl acetate, washed with water and brine. The organic layer was separated, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified by column chromatography on a silica gel (hexane:ethyl acetate = 2:1) to afford diphenylsulfide (88 mg, 95percent). All of the products were identified by comparison of their spectroscopic data with authentic samples.[34]
87% With indium; tantalum pentachloride In acetonitrile at 20℃; for 1 h; Sonication General procedure: Indium powder (229 mg, 2.0 mmol) and tantalum(V) chloride(358mg, 1.0mmol)weremixed inCH3CN(5 mL). The resultingmixture was sonicated for 0.5 h to produce a solution of the lowvalenttantalum–indium complex. Diphenyl sulfoxide (101 mg,0.5 mmol) was then added to this solution and the reactionmixturewas stirred for 3.0 h at room temperature. The progressof the reaction was followed by TLC. On completion, the solventwas removed under reduced pressure and the residue wasextracted successively with ethyl acetate, washed with water andbrine. The organic layerwas separated and dried over anhydrousNa2SO4. The crude product was purified by column chromatographyon silica gel (hexane:ethyl acetate=2:1) to afford diphenylsulfide (86mg, 92percent). All of the productswere identified by comparisonof their spectroscopic data with authentic samples.

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  • 2
  • [ 3446-90-0 ]
  • [ 37794-15-3 ]
  • [ 3446-89-7 ]
YieldReaction ConditionsOperation in experiment
59% With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In n-heptane at 80℃; for 24 h; General procedure: A mixture of catalyst PS–PEG-TD2–Cu(OAc)2 (100 mg, 0.05mmol Cu), BnOH (1a, 27.0 mg, 0.25 mmol), and TEMPO (7.8 mg,0.05 mmol) in heptane (2.0 mL) was stirred at 80 °C for 24 hunder air (1 atm). The mixture was then cooled and filtered, andthe resulting solid material was washed with Et2O (3 × 2 mL).The organic phases were combined, concentrated to a volume of2 mL, and the internal standard was added to determine the GCyield. The crude product was purified by column chromatography[silica gel, hexane–Et2O (99:1)]. In the formation of somebenzaldehydes, low isolated yields were observed because ofinstability of the benzaldehydes on silica gel
Reference: [1] Synlett, 2018, vol. 29, # 9, p. 1152 - 1156
[2] Organic Letters, 2006, vol. 8, # 1, p. 167 - 170
[3] Mendeleev Communications, 2010, vol. 20, # 4, p. 185 - 191
  • 3
  • [ 3446-90-0 ]
  • [ 3446-89-7 ]
YieldReaction ConditionsOperation in experiment
95% With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; C110H202N8O47; oxygen; copper(II) bis(trifluoromethanesulfonate); potassium carbonate In water at 20℃; for 12 h; Green chemistry General procedure: To a 48 mL tube, were added Cu(II) or Cu(I) salt (0.05 mmol), PEG-PyTa (0.025 mmol) and H2O (3.0 mL). The mixture was stirred for 30 min at room temperature and a clear dark-blue solution was observed. Then alcohols (1.0 mmol), TEMPO (0.05 mmol), and K2CO3 (0.2 mmol) were sequentially added, followed by connecting a balloon of oxygen. The reaction mixture was stirred at room temperature until the reaction completed based on GC analysis. After that, the reaction mixture was extracted with MTBE (3 mL×3) and the extracts were combined, dried over anhydrous Na2SO4 and concentrated under vacuum. Finally, the residue was purified by flash chromatography on silica to afford the desired aldehydes.
94% With Cu2(ophen)2; oxygen In acetonitrile at 60℃; for 12 h; Green chemistry General procedure: To a 10mL round bottom flask, the mixture of 12 benzylalcohol 1a (1.0mmol, 0.104mL) and Cu2(ophen)2 (0.05mmol, 26mg,) in 60 CH3CN (4mL), was stirred in oil bath at 60°C under oxygen atmosphere (oxygen ball). The reaction was monitored and conversions were determined by GC–MS.
90% With chloroamine-T; zinc dibromide In acetonitrile for 2 h; Reflux General procedure: A CH3CN solution of alcohol (1 mmol), ZnBr2 (45 mg, 0.2 mmol), and chloramine-T (282 mg, 1 mmol) was placed in a three necked flask with a reflux condenser. After the mixture was stirred under reflux for 1.5-5 h. After cooling to room temperature, the solution was quenched by adding water and the resulting mixture was extracted with AcOEt. Removal of the solvent under reduced pressure gave the crude product, which was purified by column chromatography on silica gel to give the corresponding carbonyls.
90% With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium carbonate; N-Phenylglycine; copper(ll) bromide In water for 3 h; Reflux; Schlenk technique General procedure: A mixture of p-methylbenzyl alcohol (1.0 mmol), N-phenylglycine(0.0076 g, 0.05 mmol), CuBr2 (0.0112 g, 0.05 mmol),Na2CO3 (0.1060 g, 1.0 mmol), TEMPO (0.0078 g, 0.05 mmol),H2O (3.0 mL) were added to a 100 mL Schlenk tube, which wasvigorously stirred in air under reflux for 0.5 h. After the reaction,the product was extracted with CH2Cl2 (3 × 2.0 mL). Thecombined organic phase was washed with H2O (3.0 mL) anddried over anhydrous MgSO4. After concentration undervacuum, the residue was purified by column chromatography toafford p-methylbenzaldehyde.Isolated yield: 0.1080 g (90percent).
90% at 80℃; for 20 h; General procedure: In a 150 mL thick-walled pressure tube equipped with a magnetic stirrer,In an air atmosphere,To the system was added benzyl alcohol (i.e., R1 in formula (I) H) 1.0 mmol (108.1 mg)Ammonia (1.6 x 10-2 mol / L) 5.0 mL,5 molpercent (9.5 mg) of cuprous iodide,TEMPO 5 molpercent (7.8 mg),100 & lt; 0 & gt; C for 12 h,After the reaction is over,The reaction solution was cooled to room temperature,And extracted with ethyl acetate (3 x 5.0 mL). The organic layers were combined and concentrated in vacuo to remove ethyl acetate to give the crude product. The crude product was purified by column chromatography(Petroleum ether: ethyl acetate = 10: 1) to give the pure desired product.The yield of 97.6 mg was 92percent.
86% With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; iodic acid In N,N-dimethyl-formamide at 20℃; for 2 h; Inert atmosphere General procedure: To a solution of 1-(p-bromophenyl)ethanol I-23 (201 mg, 1.0 mmol) in DMF (2.0 mL) was added HIO3 (194 mg, 1.1 mmol) and TEMPO (7.8 mg, 0.05 mmol). The mixture was stirred for 2 h at room temperature under an Ar atmosphere. After the reaction, the reaction mixture was poured into aq Na2S2O3, and extracted with a mixture of Et2O: hexane=1:1 (3*10 mL). Then, the organic layer was poured into satd NaCl (10 mL) and extracted with Et2O (10 mL). The organic layer was dried over Na2SO4. After being filtration and removal of the solvent under reduced pressure, the residue was purified by flash short column chromatography on silica gel (EtOAc-hexane, 1:4) to give p-bromoacetophenone II-23 in 99percent yield.
80% With indium isopropoxide; pivalaldehyde In chloroform at 20℃; for 3 h; Glovebox; Sealed tube; Inert atmosphere General procedure: To a screw tube in a glovebox was added In(Oi-Pr)3 (29.2 mg, 0.1 mmol). The tube was then sealed and removed from the glovebox, and CHCl3 (1 mL), alcohol (0.5 mmol), and pivalaldehyde (280 μL, 2.5 mmol) were added under N2 in this order. After stirring the mixture at r.t. for 3 h, H2O (1.0 mL) was added to the reaction mixture, which was then extracted with EtOAc. The organic phase was dried (Na2SO4), and evaporated under reduced pressure. The crude material was purified by silica gel column chromatography (Table 2 and Scheme 2).
78% With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; C20H36N5(3+)*3Br(1-); oxygen; copper In water at 35℃; for 6 h; Schlenk technique General procedure: A 30-mL Schlenk tube was evacuated and filled with O2, the benzyl alcohol (1 mmol), Cu powder (5percent mol), imidazolium (5percent mol), TEMPO (5percent mol), and H2O (3 mL) was added and stirred at 35 °C under an O2 atmosphere by connecting an O2 balloon. When the reaction was complete, the mixture was extracted with CH2Cl2 (3 × 10 mL). The combined extracts were dried (MgSO4). Then the solvent was removed and the mixture was purified by column chromatography (silica gel) to give the product.
90 %Chromat. With oxygen; potassium carbonate In toluene at 90℃; General procedure: In a 5 ml glass flask, catalyst (10 mg, containing 0.2 molpercent Pd), alcohol(0.5 mmol), K2CO3 (104 mg, 0.75 mmol) and H2O or toluene(2 mL) were added and reaction mixture was stirred continuously at90 °C for the desired time under O2 atmosphere (from a balloon). Then,in the case of water as solvent, products were extracted with ethylacetate and the catalyst was recovered by an external magnet. Yields ofdesired products were determined by gas chromatography.

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  • 4
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  • [ 3446-89-7 ]
YieldReaction ConditionsOperation in experiment
92% at 130℃; for 12 h; Sealed tube; Inert atmosphere General procedure: An oven dried pressure tube was chargedwith aryl bromide (1 mmol), CuI (1 mmol), DABCO (2 mmol) and dry DMSO (5 mL).Then the tube was sealed with a teflon cap and heated with stirring at 130 Cin N2 atmosphere for 12 – 36 h. The completions of reactions weremonitored by TLC. The reaction mixture was then cooled to room temperature. Themass was passed through celite bed, packed in a sinter funnel. Then thefiltered reaction mixture was extracted with ethyl acetate (3 X 20) washed withwater (3 X 20) and brine solution (3 X 10). Ethyl acetate part were collectedand dried over Na2SO4, and then evaporated under reducedpressure. The crude products were purified by column chromatography on silicagel to obtain pure product.
70% at 135℃; for 36 h; General procedure: An oven dried pressure tube was charged with aryl halide (0.5mmol), CuI (10–25molpercent), anhydrous Zn(OAc)2 (1.5–2equiv) and anhydrous DMSO (1.6mL). The tube was sealed with a Teflon screw cap and stirred at 135°C for 24–36h. The reaction mixture was then cooled to room temperature and stirred in 10mL of diethyl ether for 5min. It is filtered through a sintered funnel and the filtrate is washed with excess ice cold water and further extracted with diethyl ether (3×10mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to give the crude product, which was purified by column chromatography using 200–400 mesh silica gel and a mixture of diethyl ether and hexane (or pentane, for Table 2, entries 2, 8, 10, 14, 16 and 24) as eluents to afford the desired products in good yields.
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[2] Chemical Communications, 2011, vol. 47, # 18, p. 5304 - 5306
[3] Tetrahedron, 2013, vol. 69, # 38, p. 8276 - 8283
  • 5
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  • [ 3446-89-7 ]
YieldReaction ConditionsOperation in experiment
60% With N-ethyl-N,N-diisopropylamine In water at 189℃; for 48 h; General procedure: To a round bottomed flask equipped with magnetic stir bar and reflux condenser were added: the aryl halide (2.0 mmol), dimethylsulfoxide (10 mL), N,N-diisopropylethylamine (0.35 mL, 2.0 mmol), and water (approximately 0.04 mL, 2.0 mmol). The reaction was heated to reflux temperature (189 °C) in a sand bath and stirred for the specified time. Reaction progress was monitored by TLC and/or 1H NMR analysis. When complete consumption of the starting material was evident, the reaction was cooled to room temperature extracted with ethyl acetate (x3) and the combined organic extracts were washed with 2 M HCl, brine, and dried over MgSO4.The solvent was removed en vacuo and the crude product was purified by column chromatography on silica gel (Hexanes/EtOAc, gradient elution).
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 38, p. 5323 - 5326
  • 6
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  • [ 68-12-2 ]
  • [ 3446-89-7 ]
YieldReaction ConditionsOperation in experiment
89.2% at -5 - 45℃; for 7 h; In a 500 mL dry three-necked flask, add DMF (150 mL), thioanisole (100.0 g), and cool to -5°C -5°C.150.0 g of phosphorus oxychloride was slowly added dropwise. During the addition, the internal temperature was kept between -5°C and 5°C. After the dripping is completed,Slowly raise the reaction temperature between 35-45°C, stir the reaction for 7 hours, and check the reaction by TLC.After the reaction was completely completed, the reaction solution was cooled to room temperature, and the reaction solution was slowly added to 500 mL of ice water, keeping the temperature not higher than 35°C.After the completion of the transfer, and stirring at not more than 35 ° C for 10 minutes, add 200mL of dichloromethane, with 10percent sodium hydroxide to adjust the pH to 7-8, separate the organic phase,Continue to extract once with 200 mL of methylene chloride. Combine the organic phases and dry over anhydrous sodium sulfate.The organic solvent was distilled off, distillation was continued, and a fraction between 85-90°C was collected to obtain 109.4 g of a colorless transparent liquid in a yield of 89.2percent.
Reference: [1] Patent: CN107556223, 2018, A, . Location in patent: Paragraph 0028-0030
  • 7
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  • [ 13205-48-6 ]
  • [ 3446-89-7 ]
YieldReaction ConditionsOperation in experiment
83 %Chromat. With oxygen; potassium carbonate In water at 90℃; General procedure: In a 5 ml glass flask, catalyst (10 mg, containing 0.2 molpercent Pd), alcohol(0.5 mmol), K2CO3 (104 mg, 0.75 mmol) and H2O or toluene(2 mL) were added and reaction mixture was stirred continuously at90 °C for the desired time under O2 atmosphere (from a balloon). Then,in the case of water as solvent, products were extracted with ethylacetate and the catalyst was recovered by an external magnet. Yields ofdesired products were determined by gas chromatography.
Reference: [1] Applied Catalysis A: General, 2018, vol. 563, p. 185 - 195
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Reference: [1] ACS Catalysis, 2018, p. 11134 - 11139
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Reference: [1] Angewandte Chemie - International Edition, 2016, vol. 55, # 5, p. 1854 - 1858[2] Angew. Chem., 2015, vol. 128, # 5, p. 1886 - 1890,5
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  • [ 50-00-0 ]
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