1534-08-3

Usage

Uses

Used in Flavor and Fragrance Industry:
S-METHYL THIOACETATE is used as a flavoring agent for its ability to impart a fruity and sulfury aroma to various products. It is particularly useful in the creation of artificial fruit flavors, enhancing the taste and smell of food and beverages.
Used in Chemical Synthesis:
S-METHYL THIOACETATE serves as an important building block in the synthesis of various organic compounds. Its reactivity and versatility make it a valuable intermediate in the production of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in the Cosmetics Industry:
In the cosmetics industry, S-METHYL THIOACETATE is used as a fragrance ingredient to add a pleasant and distinctive scent to personal care products such as perfumes, lotions, and shampoos.
Used in the Pharmaceutical Industry:
S-METHYL THIOACETATE is used as a key intermediate in the synthesis of various pharmaceutical compounds, contributing to the development of new drugs and therapies.
Used in the Agrochemical Industry:
S-METHYL THIOACETATE is employed as a starting material in the production of agrochemicals, such as pesticides and herbicides, due to its unique chemical properties and reactivity.

InChI:InChI=1/C2H4O2.CH4S/c1-2(3)4;1-2/h1H3,(H,3,4);2H,1H3/p-1

Upstream product

• 463-51-4 Ketene 
• 74-93-1 methylthiol 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 21119-13-1 thioacetic acid O-methyl ester 
• 507-09-5 tiolacetic acid 
• 7647-01-0 hydrogenchloride 
• 58276-22-5 methyl N-phenyl ethanimidothioate 
• 74-88-4 methyl iodide 
• 81956-70-9 (carboxymethyl)(methyl thioacetate)bis(dimethylglyoximato)cobalt(III) 
• 1353674-12-0 3,3-dimethyloxathiirane 
• 174501-65-6 1-butyl-3-methylimidazolium Tetrafluoroborate 
• 10387-40-3 potassium thioacetate 
• 93111-02-5 3-methyl-thiolane-1-oxide 

Downstream Products

• 88354-91-0 N-[2-(4-Phenoxy-phenoxy)-ethoxy]-thioacetimidic acid methyl ester 
• 463-51-4 Ketene 
• 74-93-1 methylthiol 
• 624-92-0 Dimethyldisulphide 
• 5813-48-9 Methanesulfenyl chloride 
• 75-36-5 acetyl chloride 
• 52069-53-1 2-[(cyanomethyl)thio]acetic acid methyl ester 
• 493010-95-0 (2S)-2-[(1R,2S)-2-benzyloxycarbonyl-1-methylsulfanyl-propyl]-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 890653-76-6 (S)-2-((1R,2R)-2-benzyloxycarbonyl-1-methylsulfanyl-propyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 507-09-5 thioacetic acid 

Relevant academic research and scientific papers

Acid-Catalyzed Hydrolysis of 1,1-Bis(methylthio)ethene. Buffer- and Thiol-Dependent Changes in the Rate-Determining Step

Acid-catalyzed hydrolysis of 1,1-bis(methylthio)ethene has been studied kinetically in 10percent aqueous acetonitrile at 30 deg C.The rate increased with buffer concentration, showing saturation at higher concentrations.Addition of 2-mercaptoethanol had little influence on the rate at the limiting zero buffer concentration, but it greatly accelerated the reaction in buffer solutions and followed a saturation curve.It was concluded that the rate-determining step is largely the protonation of the double bond at zero buffer concentration (k2/k-1 = 3.13) but it changes to the attack of water on the intermediate carbenium ion as the buffer concentration increases.The 1H NMR spectral analysis of the reaction products in 80percent CH3CN-D2O showed that the H-D isotope exchange at the 2-position of the substrate occurred extensively in a formate buffer but only moderatly in a DCl solution during the hydrolysis.

NMR STUDIES AND STRUCTURAL ASSIGNMENT OF PAEDEROSIDE

Detailed and extensive nmr analyses of paederoside have been carried out resulting to allow complete assignement of all of the 1H an 13C signals.The results provided unambiguous bases to support methyl thiocarbonate structure (3) for paederoside, a novel natural sulfur-containing iridoid glucoside of Paederia scandens.

Convenient synthesis of alkyl thioacetate from alkyl halide using a polymer-supported sodium thioacetate

Alkyl halides are efficiently converted to their corresponding S-alkyl thioacetates under mild and nonaqueous conditions, using polymer-supported sodium thioacetate as a new polymeric reagent at room temperature in high yields and purity. The spent polymeric reagent can be removed quantitatively by filtration and pure products can be obtained by evaporation of the solvent. The spent polymeric reagent can be regenerated and reused several times without its activity changing appreciably. Iranian Chemical Society 2012.

Photochemical formation and reactivities of substituted oxathiiranes in low-temperature argon matrices

Thiocarbonyl S-oxides (sulfines) derived from aliphatic and cycloaliphatic thioketones were irradiated in argon matrices at 10 K, and the resulting oxathiiranes were identified by comparison of computed and experimental IR spectra. Upon photolysis at 10 K, depending on the substitution pattern, the oxathiiranes underwent either H-shift reactions or regioselective ring enlargements to form the corresponding thioesters. After warming of the matrix material to 38-40 K, the oxathiiranes underwent fast desulfurization to yield the corresponding ketones. Density functional theory (DFT) computations at the B3LYP/6-311+G(3df,3pd) level suggest that the desulfurizations of oxathiiranes occurred as bimolecular processes with activation enthalpies near 0 kcal mol-1.

Unexpected microwave reaction of 1,3-disubstituted imidazolium salts: A novel synthesis of 1,3-disubstituted imidazole-2-thiones

Microwave-promoted reaction of 1,3-disubstituted imidazolium salts with potassium thioacetate or potassium thiocyanate under solvent-free conditions provided a rapid and efficient synthesis of 1,3-disubstituted imidazole-2-thiones. Copyright Taylor & Francis Group, LLC.

The regiochemistry of cyclization of α-sulfenyl-, α-sulfinyl-, and α-sulfonyl-5-hexenyl radicals: Procedures leading to regioselective syntheses of cyclic sulfones and sulfoxides

A study of the cyclization of α-sulfenyl-, α-sulfinyl-, and α-sulfonyl-5-hexenyl and 5-methyl-5-hexenyl radicals reveals a unique contrast in the mode of ring closure of the radicals. In the case of the 5-hexenyl radicals, the sulfinyl-substituted species displays unexpected regioselectivity relative to its analogues. Thus, while the α-S- and α-SO2-5-hexenyl radicals give measurable and increasing quantities of 6-endo product, the α-sulfinyl species cyclizes with high selectivity (95.5:4.5) via a 5-exo mode. By contrast, ring closure of the 5-methyl-5-hexenyl radicals is found to give substantially the 6-endo product in all cases. It is the α-sulfonyl-5-methyl-5-hexenyl radical that now exhibits high regioselectivity (97.5:2.5) for 6-endo closure: an illustration of the synthetic value of this observation is the independent synthesis of the model cyclohexyl sulfone 61 in high yield. It is found that ring closure under the conditions employed occurs irreversibly in all cases.

Heteroatom functionalized α-methyl ketones

The present invention relates to functionalized ketones and novel processes for synthesizing those ketones. The processes of this invention are especially well suited for synthesizing α-methyl leaving group functionalized ketones. This invention also relates to processes for using α-methyl leaving group functionalized ketones to produce other compounds and intermediates useful in those processes.

Chemoselective synthesis of aliphatic sulfines by direct oxidation of dithioesters

Oxidation of enethiolizable dithioesters with mCPBA affords the corresponding sulfines (thiocarbonyl S-oxides) quantitatively, with a high chemoselectivity.This reaction is (E) stereoselective: delivery of the oxygen proceeds from the side opposite the alkylthio group.The thermal stabilities of these new molecules have been evaluated.The competitive oxidation of various thiocarbonyl compounds has been examined. Key words: sulfines / thiocarbonyl oxides / dithioesters / oxidation / heterocumulenes / organic synthesis / sulfur compounds

Acid-Catalyzed Hydrolysis of Ketene Dithioacetals and Trithioorthocarboxylates. Effect of β-Methyl Substitution

Hydrolysis rates of β-methyl-substituted ketene dithioacetals were measured. β-Monomethyl and β,β-dimethyl substitutions reduced the reactivity of the parent acetal by factors of 26 and 6.7 x 105, respectively.Similar methyl substitutions of trithioorthoacetate, however, enhanced the hydrolysis reactivity by 3 and 23 times.The reversibility of protonation of ketene dithioacetal during hydrolysis was slightly increased by a β-methyl group, but dimethyl substitution seemed to inhibit reversibility by raising the potential barrier to protonation.

SYNTHESIS OF MONO- AND 1,4-DICARBONYL COMPOUNDS BASED ON THE OXYGENATION OF PHOSPHONATE CARBANIONS. SYNTHESIS OF DIHYDROJASMONE, ALLETHRONE AND METHYLENOMYCIN B

Oxidation of the α-alkylthio-substituted phosphonate carbanions was found to give the corresponding carbonyl compounds.A new synthesis of 1,4-dicarbonyl systems involving the oxygenation of phosphonate carbanions as a key step is described.Total synthesis of dihydrojasmone and allethrone and formal synthesis of methylenomycin B is reported.