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CAS No. : | 63547-22-8 | MDL No. : | MFCD05262040 |
Formula : | C15H14O2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HTHFEDOFDBZPRX-UHFFFAOYSA-N |
M.W : | 258.34 | Pubchem ID : | 2077886 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
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* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94.17% | Example 1; Preparation of 2-[(Diphenylmethyl)sulfinyl] acetic acid; 2-[(Diphenylmethyl)thio] acetic acid (416 g, 1.61 mol) was suspended in purified water(4160 ml) at 25 to 300C. This was followed by the addition of 30% sodium hydroxide solution [prepared by dissolving of 70.90 g (1.77 mol) of sodium hydroxide flakes/pellets in 235 ml of purified water] over a period of 15 minutes at 25 to 3O0C. Next, 50% of hydrogen peroxide (142.5 g, 2.095 mol) was added in 5 to 6 hours maintaining <n="16"/>temperature 25 to 35C under agitation. The reaction mixture was further stirred for 15 to 20 hours at 25 to 350C. After completion of the reaction (starting material should be less than 0.5% by area) toluene (1664 ml) was added and the reaction mixture was stirred for 10 minutes. The resulting biphasic mixture was acidified with concentrated hydrochloric acid (250 ml) under stirring while maintaining the temperature between 25 to 3O0C. The resulted mass further stirred at 25 to 3O0C for 1 hour. The precipitated product was collected by filtration, washed with water (3 x 832 ml) followed by toluene (416 ml) and dried to produce 416 g of 2-[(diphenylmethyl)sulfmyl] acetic acid as a white crystalline powder (Yield: 94.17%; HPLC Purity: 99.3% by area). | |
88.15% | With tert.-butylhydroperoxide;vanadium(III) 2,4-pentanedionate; In methanol; toluene; at 0 - 30℃; for 6.58333 - 7.75h;Product distribution / selectivity; | Example 5; Preparation of 2-[(DiphenyImethyI)sulfinyl] acetic acid; 2-[(Diphenylmethyl) thio] acetic acid (5 g) was dissolved in toluene: methanol (10:1, 55 ml) at 25 to 300C and the resulting mass was cooled at 0 to 50C. This was followed by the addition of vanadium acetyl acetonoate (0.04 g) and stirred the reaction <n="18"/>mass for 15 minutes at 0 to 50C. The tert-butylhydroperoxide (70% solution, 3.54 g) was added at 0 to 50C under stirring over period of 20 to 30 minutes. The reaction mixture was further stirred for 6 to 7 hours at 0 to 5C. Next, water (100 ml) was added to the reaction mixture and stirring continued for 1 hour at 10 to 15C. The precipitated product was collected by filtration, washed with water (3 x 100 ml) followed by toluene (50 ml) and dried to give the 2-[(diphenylmethyl) sulfinyl] acetic acid as a crystalline powder (Yield = 88.15%; HPLC Purity: 98.16% by area). |
87.15% | Example 4; Preparation of 2-[(DiphenylmethyI)sulfinyl] acetic acid; 2-[(Diphenylmethyl) thio] acetic acid (10 g) was dissolved in methanol (50 ml) at 25 to 3O0C. This was followed by the addition of ammonium molybdate (0.40 g) and stirring the reaction mass for 15 minutes at 25 to 300C. The reaction mixture was cooled at 10 to 150C followed by the addition of sodium per carbonate (5.0 g) at 10 to 150C under stirring. The reaction mixture was further stirred for 12 to 14 hours at 20 to 25C.This was followed by the addition of purified water (200 ml) and toluene (50 ml) under stirring for 10 minutes. The resulting biphasic mixture was acidified with cone. hydrochloric acid at pH less than 2 under stirring maintaining temperature at 25 to 300C.The resulted mass further stirred at 25 to 3O0C for 1 hour. The precipitated product was collected by filtration, washed with water (3 x 100 ml) followed by toluene (100 ml) and dried to give the 2-[(diphenylmethyl) sulfinyl] acetic acid as crystalline powder (Yield: 87.15%; HPLC Purity: 95.70% by area). |
78.58% | Example 3; Preparation of 2-[(Diphenylmethyl)sulfmyl] acetic acid; 2-[(Diphenylmethyl) thio] acetic acid (5 g) was suspended in purified water (50 ml) at 25 to 3O0C. This was followed by the addition of (-)-(alpha)-methyl benzyl amine <n="17"/>(2.345 g) and stirred the reaction mass for 15 minutes at 25 to 3O0C. The reaction mixture was further heated at 40 to 45C followed by addition of sodium hypochlorite (5.28%, 33 ml) over period of 30 minutes. The reaction mixture was further stirred for 2 to 2.5 hours at 40 to 450C. The reaction mass was cooled to 25 to 3O0C which is then followed by the addition of toluene (20 ml) and stirred the reaction mixture for 10 minutes. The resulting biphasic mixture was acidified with cone, hydrochloric acid under stirring at 25 to 300C. The resulted mass further stirred at 25 to 3O0C for 1.5 hour. The precipitated product was collected by filtration, washed with water (3 x 50 ml) followed by toluene (50 n) and dried to give the 2-[(diphenylmethyi) sulfmyl] acetic acid as a crystalline powder (Yield: 78.58%; HPLC Purity: 99.4% by area). | |
60.28% | Example 2; Preparation of 2-[(Diphenylmethyl)sulfinyl] acetic acid; 2-[(Diphenylmethyl) thio] acetic acid (25 g) was suspended in purified water (100 ml) at 25 to 300C. This was followed by the addition of 30% sodium hydroxide solution (prepared by dissolving of 16.0 g of sodium hydroxide flakes/pellets in 50.0 ml purified water) over a period of 15 minutes at 25 to 3O0C. The reaction mass was heated to 40 to 450C. Further N-chlorosuccinimide (20.0 g) was added in 1 to 1.5 hours maintaining temperature 40 to 45C under agitation. The reaction mixture was further stirred for 10 to 12 hours at 40 to 450C. The reaction mass was cooled to 25 to 3O0C after the completion of reaction followed by the addition of toluene (100 ml) and reaction mixture further stirred for 10 minutes. The resulting biphasic mixture was acidified with 50% aqueous sulfuric acid under stirring maintaining temperature at 25 to 300C. The resulted mass was further stirred at 25 to 3O0C for 1 hour. The precipitated product was collected by filtration, washed with water (3 x 100 ml) followed by toluene (100 ml) and dried to give the 2-[(diphenylmethyl) sulfinyl] acetic acid as a white crystalline powder (Yield: 60.28%; HPLC Purity: 98.50% by area). | |
51.81% | Example 6; Preparation of 2-[(Diphenylmethyl)sulfinyl] acetic acid; Sodium perborate (15.30 g) was suspended in purified water (23 ml) at 25 to 300C. The resulting mass was cooled to 10 to 15C. This was followed by addition of acetic anhydride: methanol solution (1:1, 10.2 g dissolved in 10.2 g of methanol) at 10 to 150C and continued stirring for 15 minutes at 10 to 150C. The reaction mass was further cooled to -20 to -250C followed by the addition of 2-[(diphenylmethyl) thio] acetic acid solution (20 gm dissolved in 220 ml toluene: methanol, 10:1) at -10 to -150C under stirring over period of 2.5 hours. The reaction mixture was further stirred for 2 hours at -10 to -15C. The reaction temperature was increased to 0 to 5C followed by stirring for 2 hours. Then reaction mass was added to purified water (600 ml) and acidified with cone, hydrochloric acid to below 2.0 pH. The resulting precipitate was stirred for 15 minutes. The precipitated product was collected by filtration and washed with water (3 x 100 ml) and toluene (100 ml) and dried to give the 2-[(diphenylmethyl) sulfinyl] acetic acid as a crystalline powder (Yield = 51.81%, HPLC Purity: 97.0% by area). | |
With dihydrogen peroxide; In water; at 20℃; for 3h; | E. Synthesis of 2-(benzhvdrylsulfinyl)acetic acid; [0081] 10 g of thiourea was dissolved in 57 ml of 48% HBr and 10 ml of water. The reaction mixture was heated to 60 0C, and 20.2 g of benzhydrol was added. The temperature was increased to 9O0C and then cooled to room temperature. The crystals were filtered off and washed with water. The crystals were added to 35ml 30% sodium hydroxide and the mixture was heated to 70 0C, before 11.44 g chloroacetic acid in 22 ml of water was added slowly. The mixture was refluxed for half an hour after the addition. 14.3 ml hydrogen peroxide (30%) was added to the above solution within 3 hours at room temperature. 22 ml of water was then added and the reaction mixture was filtered. The filtrate was acidified with concentrated HCl (d=1.18). The resulting solid was filtered off and dried to give 13 g of the desired product. | |
With dihydrogen peroxide; acetic acid; In methanol; | Step II: Oxidation of the benzhvdryl thio acetic acid with hydrogen per oxide and acetic acid in acetonitrile to obtain benzhvdryl sulfinyl acetic acid:10 g of benzhydryl thio acetic acid was charged to 100 mL of methanol. To it 10 mL of acetic acid and 17g (50%) of hydrogen peroxide was added drop wise and the reaction mixture stirred for 6-8hours. The reaction was monitored till benzhydryl thio acetic acid was not more than 1%. 300 mL of DM water was added and the reaction <n="10"/>mixture stirred. The solid was filtered, washed with water and dried under vacuum at 45-50 0C. Yield: 8.0 g Purity: 98-99% | |
91%Chromat. | With dihydrogen peroxide; In 1,2-dichloro-ethane; at 20℃; for 1.5h; | General procedure: To examine the catalytic activity of the heterogeneous catalyst, 1 mmol of sulde,1.5 ml of hydrogen peroxide 30 % as oxidant and 5 % mol of catalyst weredissolved in 3 ml solvent and reacted at room temperature for different times(Scheme 4; Table 1; Fig. 7). The monitoring of the sulfoxide formation was carried out by TLC (n-hexanes:EtOAc, 1:1 or CHCl3:MeOH, 9:1 as eluent). Aftercompletion of the reaction, the solvent was evaporated and the crude product waspuried by a recrystallization method (using EtOAC/n-hexane) (Table 2). Thecatalyst was recovered and reused for further runs. |
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