Structure of 1438-91-1
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CAS No. : | 1438-91-1 |
Formula : | C6H8OS |
M.W : | 128.19 |
SMILES Code : | CSCC1=CC=CO1 |
MDL No. : | MFCD00009604 |
InChI Key : | SKSFHXVDHVKIBN-UHFFFAOYSA-N |
Pubchem ID : | 518937 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H227-H315-H319 |
Precautionary Statements: | P210-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P370+P378-P403+P235-P501 |
* 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 |
---|---|---|
99% | With dihydrogen peroxide; In neat (no solvent); at 35℃; for 0.333333h; | General procedure: H2O2 (30%, 0.4 mL) was added to a mixture containing sulfide(1 mmol) and catalyst (Zr(IV)-Schiff base-MCM-41, 0.03 g)at 35 C under solvent-free conditions. The reaction mixturewas stirred until completion of the reaction as monitored bythin-layer chromatography (TLC). After complete conversion ofthe reactant, the product was extracted with CH2Cl2 andwashed with water. The organic layer was dried over anhydrousNa2SO4. The solvent was removed under vacuum and theresidue purified by chromatography (eluting with 4:1 hexane/acetone). |
96% | With dihydrogen peroxide; In neat (no solvent); at 35℃; for 0.25h;Green chemistry; | General procedure: A mixture of sulfide (1 mmol), H2O2 (0.4 mL) and M-Salen-MNPs (0.02 g) was stirred at 35 C under solvent-free conditionand the progress of the reaction was monitored by TLC. After completion of the reaction, catalyst was separated using external magnet and washed with ethyl acetate, and next, the product wasextracted with ethyl acetate. The organic layer was dried overanhydrous Na2SO4 (1.5 g). Finally, the organic solvents were evaporated,and products were obtained in good to high yield. |
96% | With dihydrogen peroxide; at 20℃; for 0.116667h; | General procedure: H-ZSM5 (12 mg) was added to a mixture of sulfide (1 mmol) and 30% H2O2 (2.4 equiv), then the mixture was stirred at room temperature under solvent-free conditions and the progress of the reaction was monitored by Thin-layer chromatography (TLC) (EtOAc/n-hexane, 1/2). After completion of the reaction, EtOAc (5 mL) was added, the catalyst was separated by filtration, and washed with additional EtOAc (5 mL). The organic layer was washed with brine (5 mL) and dried over anhydrous Na2SO4. Finally, the organic solvent was evaporated, and products were obtained in good to high yield. All the products are known and were characterized by comparing their spectral and physical data with those of authentic samples. |
95% | With dihydrogen peroxide; In ethanol; at 20℃; for 0.75h;Green chemistry; | General procedure: Dopamine sulfamic acid-functionalized magnetic Fe3O4 nanoparticles (DSA(at)MNPs) (0.02 g) were added to solution of sulfide (1 mmol) and 33 %H2O2 (0.5 mL) in ethanol (10 mL), the mixture was stirred at room temperature for the specified time, and the progress of the reaction was monitored by thin-layer chromatography (TLC). After completion of the reaction, the catalyst was separated using an external magnet. The product was extracted with CH2Cl2, washed with water (5 mL), and dried under vacuum at room temperature. |
95% | With dihydrogen peroxide; In water; at 20℃; for 0.166667h; | General procedure: The sulfide (1 mmol) was added to a mixture of 30% H2O2 (3.6 mmol) and MNPs-PhSO3-Sc(OTf)2 (25 mg), and the mixture was then stirred at room temperature for the time specified. The progress of reaction was monitored by TLC (EtOAc/n-hexane, 3/10). After completion of the reaction, the catalyst was separated from the reaction mixture by an external magnet and the mixture was decanted. The product was extracted with Et2O (2×5 mL) and the combined organic phases were washed with brine (10 mL) and dried over anhydrous Na2SO4. The evaporation of solvent under reduced pressure gave the pure products in 90-98% yields. All the products were known and characterized by comparison of their 1H NMR spectra and physical properties (melting point) with those of authentic samples [19-22]. |
93% | With dihydrogen peroxide; In ethanol; at 20℃; for 0.166667h;Green chemistry; | General procedure: The catalyst (0.010 g) was added to solution of sulfide (1 mmol) and H2O2 (0.5 mL) in ethanol (2 mL). The reaction mixture was stirred at room temperature, and the progress of the reaction was monitored by TLC (acetone:n-hexane, 2:8). After completion of the reaction, catalyst was separated by an external magnet and washed with ethyl acetate; next, the product was extracted with ethyl acetate (5 mL 9 4). The organic layer was dried over anhydrous Na2SO4 (1.5 g). Finally, the organic solvents were evaporated, and the corresponding sulfoxides were obtained in high to excellent yields (88-99%). |
90% | With dihydrogen peroxide; In neat (no solvent); at 20℃; for 0.0833333h;Green chemistry; | General procedure: The sulfide (1mmol) was added to a mixture of 30% H2O2 (2.4 equiv, 1g) and MNPs-DABCO tribromide (10mg), and the mixture was stirred at room temperature for the time specified. The progress was monitored by TLC (EtOAc/n-hexane, 1/10). After completion of the reaction, the catalyst was separated from the product by an external magnet (within 5s) and the mixture was washed with Et2O (2×5mL) and decanted. The combined organics were dried over anhydrous Na2SO4 and then evaporation of diethyl ether under reduced pressure gave the pure products in 80-97% yields. |
90% | With dihydrogen peroxide; In ethanol; at 60℃; for 0.333333h; | General procedure: Fe3O4-SA-PPCA (0.04 g) was added to a mixture of sulfide (1 mmol) and H2O2 (0.5 mL) in EtOH at 60 C and the mixture was stirred for the appropriate time. The progress was monitored by TLC. After completion of the reaction, the catalyst was separated by an external magnet and the combined organics were washed with water (5 mL) and dried over anhydrous Na2SO4. The evaporation of solvent under reduced pressure gave the pure products in excellent yields. |
90% | With laccase; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; In tetrahydrofuran; aq. phosphate buffer; at 20℃; for 27h;Green chemistry; Enzymatic reaction;Quantum yield; | General procedure: Thioether (1 mmol) and TEMPO (62.5 mg, 0.4 mmol) were added to a solution of laccase (17.4 mg, 20 U) in phosphate buffer (0.1 M, 5 mL, pH=5) and THF (4 vol%). The reaction mixture was stirred under air at room temperature for an appropriate time (see Table 2). The progress was monitored by TLC (n-hexane/EtOAC, 4:1). After the completion of the reaction, the product was extracted with EtOAc (3 × 10 mL) and dried over anhydrous Na2SO4. Evaporation of the solvent under reduced pressure and purification by column chromatography (n-hexane/EtOAc) gave the desired sulfoxide. All products were known and were identified by comparison their spectra and physical data with literature values (see Supplementary material). |
82% | With dihydrogen peroxide; In neat (no solvent); at 20℃; for 0.5h;Catalytic behavior; | General procedure: A mixture of sulfide (1 mmol), H2O2 (0.4 mL) and catalyst(0.01 g) at room temperature, was stirred under solventfreecondition for the certain period of time. The reactionwas monitored by thin-layer chromatography (TLC). Uponcompletion, the reaction mixture was decanted andextracted with dicoloromethan. The organic layer was driedover anhydrous Na2SO4 (1.5 g). Finally, the organic solventswere evaporated, and products were obtained in82-99 % yield. |
80% | With salen complex of Cu(II) immobilized on Fe3O4 nanoparticles; dihydrogen peroxide; In ethanol; at 60℃; for 0.333333h; | General procedure: To a solution of sulfide (1mmol) and 33% H2O2 (0.5mL) in ethanol (10mL), Fe3O4/salen of Cu(II) as catalyst (0.05g) was added and the mixture was stirred at 60C for the specified time. After completion of the reaction, the catalyst was separated by an external magnet. The product was extracted with CH2Cl2, washed with water (5mL) and dried over anhydrous Na2SO4. Finally, the excess of solvent was removed under reduced pressure to give the corresponding pure sulfoxide. |
94.6%Chromat. | General procedure: Sulfide (1.0 mmol) was added to a solution of water (1.0 mL) and TauSi (149.0 mg), after stirring at 25 C for 15 min, 30% H2O2 (1.15 mmol) was added. Then, the resultant mixture was kept stirring at 25 C for 24.0 h. At the end of the reaction, saturated aqueous Na2SO3 (2.0 mL)was added to stop deep oxidation. The obtained solution was extracted with ethylacetate (3 × 2.0 mL), and the combined organic phase was washed with brine (2.0 mL) and dried over anhydrous Na2SO4.The obtained solution was analyzed by GC or HPLC to determine the conversion and yield with p-xylene as internal standard. | |
98.6%Chromat. | General procedure: Sulfide (1.0 mmol) was added to a aqueous solution of Brnsted acid in certain pH (2.0 mL), afterstirring at 25 C for 15 min, 30% H2O2 (1.15 mmol) was added. Then, the resultant mixture was keptstirring at 25 C for 24.0 h. At the end of the reaction, saturated aqueous Na2SO3 (2.0 mL) was added tostop deep oxidation. The obtained solution was extracted with ethyl acetate (3 × 2.0 mL), and the combinedorganic phase was washed with brine (2.0 mL) and dried over anhydrous Na2SO4. The obtained solutionwas analyzed by GC or HPLC to determine the conversion and yield with p-xylene as internal standard. | |
99%Spectr. | With diphenyl diselenide; urea hydrogen peroxide adduct; In dichloromethane; at 20℃; for 24h; | General procedure: UHP (2 mmol) was dissolved in CH2Cl2 (2 mL), and the solutionwas stirred at r.t. A solution of Ph2Se2 (1 mol%) and sulfide (2mmol) in CH2Cl2 (2 mL) was added to the UHP solution. Themixture was stirred at r.t. for 24 h or until complete conversionto sulfoxide was observed by TLC. Extraction was carried outwith CH2Cl2 (3 × 5 mL), after the addition of H2O (5 mL), and thecombined organic solutions were washed with brine (50 mL),dried (MgSO4), filtered, and the solvents removed underreduced pressure. Sulfoxide products were purified where necessaryby column chromatography. Yellow oil; numax (cm-1) 2972, 2916, 1423, 1033, 933, 744; 1H NMR (400 MHz, CDCl3): deltaH 2.52 (3H, s), 4.06 (2 H, q, J 13.92 Hz), 6.40 (2 H, m), 7.39 (1 H, dd, J 2.0 Hz) ppm; 13C NMR (100 MHz,CDCl3): deltaC 37.9, 52.2, 111.2, 143.5, 143.9 |
With dihydrogen peroxide; In water; acetonitrile; at 20℃; for 0.25h; | General procedure: A mixture of [Mn4(AsW9O34)2]10-/Tb/TiO2 (50 mg),sulfide (1 mmol), 30% H2O2 aqueous solution (6 mmol),acetonitrile (3 mL) was stirred at room temperature forthe time specified (Table 2). After the completion ofthe reaction, which was monitored by TLC (EtOAc/n-Hexane, 4/10), the water (5 mL) was added and catalystwas centrifuged. The product was extracted with CH2Cl2(3 × 5 mL) and the combined organic extractions washedwith brine (10 mL) and dried over anhydrous Na2SO4.The solvent was evaporated under reduced pressure togive the corresponding pure sulfoxide in most cases. | |
85%Spectr. | With dihydrogen peroxide; In neat (no solvent); at 20℃; for 0.25h;Catalytic behavior; | General procedure: 1.5 mmol 30% (w/w) H2O2 and 30 mg VO(CS)Fe3O4 nanocatalyst(1 mol%) were sequentially added, to sulfide (1 mmol) in a5 ml round bottom flask and the resulted mixture was magneticallystirred at ambient temperature for desired time. The reactionprogress was checked using TLC (EtOAc/n-hexane, 1/10). Aftercompletion of the reaction, the catalyst was magnetically isolatedfrom the product through only 5 s and was washed twice using %mL Et2O, decanted and dried using anhydrous Na2SO4 and diethylether evaporation under decreased pressure. The pure productswere obtained in 80-96% yields. |
88%Chromat. | With dihydrogen peroxide; In neat (no solvent); at 20℃; for 0.166667h;Catalytic behavior; | General procedure: A 5-mL round bottom flask was used as the reactor. At each synthesis trial, 30mg VO(BINE)(at)Fe3O4 nanocatalyst (0.9mol%) and 30% (w/w) H2O2 oxidant (2.0mmol) were added to 1mmol sulfide, successively, and the prepared reaction mixture was stirred for the desired time on a magnetic stirrer, at room temperature. TLC (EtOAc/n-hexane, 1/10) and GC were employed to track progress of the reaction. After reaction completion, an external magnet was applied to separate the catalyst from the reaction products (within 5s) and the reaction mixture was washed two times with diethyl ether (3mL) and decanted. The mixture of organic compounds was dried over anhydrous Na2SO4. Then, Et2O was evaporated under reduced pressure to achieve pure products in 80-96% yields. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
16.51 g (57%) | With bromine; sodium carbonate; In methanol; dichloromethane; | Preparation of 2-methylthiomethyl-2,5-dimethoxy-2,5-dihydro furan A mixture of <strong>[1438-91-1]2-methylthiomethyl furan</strong> (23.3 g, 0.182 mole), anhydrous sodium carbonate (32.16 g, 0.303 mole), methylene chloride (40 mL) and absolute methanol (40 mL) was cooled to -20 C. under nitrogen atmosphere. A solution of bromine (24.32 g, 0.152 mole) in 60 mL absolute methanol was added over a period of one hour. The reaction mixture was stirred for another 4 hours and filtered by suction. The filtrate was stirred with anhydrous potassium carbonate (10 g--1 hour) and filtered. The solvents were removed on the rotatory evaporator and methylene chloride (100 mL) was added. The organic solution was dried over anhydrous sodium sulfate, filtered and the solvent was removed on the rotatory evaporator. The residue was distilled under reduced pressure to give 16.51 g (57%) of pure product, bp 66-68 C. (0.4 mm Hg), nD =1.4860. |
16.51 g (57%) | With bromine; sodium carbonate; In methanol; dichloromethane; | Prepration of 2-methylthiomethyl-2,5-dimethoxy-2,5-dihydro furan A mixture of <strong>[1438-91-1]2-methylthiomethyl furan</strong> (23.3 g, 0.182 mole), anhydrous sodium carbonate (32.16 g, 0.303 mole), methylene chloride (40 mL) and absolute methanol (40 mL) was cooled to -20 C. under nitrogen atmosphere. A solution of bromine (24.32 g, 0.152 mole) in 60 mL absolute methanol was added over a period of one hour. The reaction mixture was stirred for another 4 hours and filtered by suction. The filtrate was stirred with anhydrous potassium carbonate (10 g-1 hour) and filtered. The solvents were removed on the rotary evaporator and methylene chloride (100 mL) was added. The organic solution was dried over anhydrous sodium sulfate, filtered and the solvent was removed on the rotary evaporator. The residue was distilled under reduced pressure to give 16.51 g (57%) of pure product, bp 66-68 C. (0.4 nm Hg), n23 =1.4860. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dihydrogen peroxide; In water; acetonitrile; at 20℃; for 0.416667h; | General procedure: A mixture of [Mn4(PW9O34)2]10-/Tb/TiO2 (50 mg),sulfide (1 mmol), 30% H2O2 aqueous solution (6 mmol)and acetonitrile (3 mL) was stirred at room temperaturefor the time specified (Table 2). After the completion ofthe reaction, which was monitored by TLC (EtOAc/n-Hexane, 4/10), the water (5 mL) was added and catalystwas centrifuged. The product was extracted with CH2Cl2(3 × 5 mL) and the combined organic extractions washedwith brine (10 mL) and dried over anhydrous Na2SO4.Evaporation of the solvent under reduced pressure givesthe pure corresponding sulfone in most cases. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
15.0 g (34%) | With potassium hydroxide; In water; | Preparation of 2-methylthiomethyl furan Finely powdered potassium hydroxide (19.97 g, 0.355 mole) was added portionwise to a cold mixture of furfuryl mercaptan (40.0 g, 0.350 mole) and iodomethane (49.72 g, 0.350 mole). The reaction mixture was allowed to stir for 6 hours and 36 mL of water were added. The solution was extracted with ether (3*300 mL) and the combined organic fractions were dried over anhydrous sodium carbonate. After the removal of the solvent, the residue was distilled under reduced pressure to give 15.0 g (34%) colorless product, bp 61 C. (20 mm Hg), nD =1.5210. |
15.0 g (34%) | With potassium hydroxide; In water; | Preparation of 2-methylthiomethyl furan Finely powdered potassium hydroxide (19.97 g, 0.355 mole) was added portionwise to a cold mixture of furfuryl mercaptan (40.0 g, 0.350 mole) and iodomethane (49.72 g, 0.350 mole). The reaction mixture was allowed to stir for 6 hours and 36 mL of water were added. The solution was extracted with ether (3*300 mL) and the combined organic fractions were dried over anhydrous sodium carbonate. After the removal of the solvent, the residue was distilled under reduce pressure to give 15.0 g (34%) colorless product, bp 61 C. (20 mm Hg), n22 =1.5210. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dihydrogen peroxide; at 20℃; for 0.133333h; | The sulfide (1 mmol) was added to a mixture of 30% H2O2(1 g,2.4 equiv) and VO(pseudoephedrine)MNPs (40 mg, 1.4 mol%), andthen the mixture was stirred at room temperature for the time spec-ified. The progress was monitored by TLC (EtOAc/n-hexane, 1/2).After completion of the reaction, the catalyst was separated fromthe product by an external magnet (within 5 s), washed with Et2O(2 × 5 mL) and decanted. The combined organics were washed withbrine (5 mL) and dried over anhydrous Na2SO4.The evaporation of Et2O under reduced pressure gave the pure products in 80-97%yields and 9-15% ee. |