4886-77-5

Usage

Uses

Used in Flavor and Fragrance Industry:
3-Methylthioanisole is used as a flavoring agent for imparting a sweet, earthy, and fruity aroma to products such as perfumes, soaps, and cleaning agents. Its natural occurrence in foods like beer, wine, coffee, and strawberries makes it a valuable addition to the creation of authentic and complex scent profiles in these industries.
Used in Pharmaceutical Applications:
3-Methylthioanisole may be utilized as a pharmaceutical compound due to its potential to inhibit certain enzymatic activities. This property suggests that it could be developed into a therapeutic agent, pending further research and development.
However, it is important to note that exposure to high concentrations of 3-Methylthioanisole can result in irritation to the eyes, skin, and respiratory system, indicating a need for careful handling and regulation in its applications.

InChI:InChI=1/C8H10S/c1-7-4-3-5-8(6-7)9-2/h3-6H,1-2H3

Upstream product

• 108-40-7 toluene-3-thiol 
• 75-15-0 carbon disulfide 
• 74-88-4 methyl iodide 
• 6257-10-9 N,N'-dicyclohexyl-O-methyl isourea 
• 33733-73-2 3-bromo-1-(methylthio)benzene 
• 624-92-0 Dimethyldisulphide 
• 28987-79-3 m-tolylmagnesium bromide 
• 625-95-6 3-Iodotoluene 
• 67-68-5 dimethyl sulfoxide 
• 17933-03-8 m-tolylboronic acid 
• 591-17-3 meta-bromotoluene 
• 1899-93-0 3-methylphenylsulfonyl chloride 
• 616-38-6 carbonic acid dimethyl ester 
• 124-38-9 carbon dioxide 

Downstream Products

• 17796-88-2 N-[(3-methylphenyl)thio]succinimide 
• 90532-02-8 1-bromo-2-methyl-4-methylsulfanylbenzene 
• 10355-06-3 methyl 3-methylphenyl sulfone 
• 13150-71-5 (+/-)-methyl m-tolyl sulfoxide 
• 35657-16-0 3-methylphenyl chloromethyl sulfide 
• 3996-30-3 2-[(3-methylphenyl)thio]acetic acid 
• 128102-46-5 2-<(Carboxymethyl)thio>-4-methylbenzoic acid 
• 858847-88-8 2-carboxymethylsulfanyl-6-methyl-benzoic acid 
• 118-90-1 ortho-methylbenzoic acid 
• 99-94-5 p-Toluic acid 
• 108297-60-5 C₉H₁₁O₃S^(1-)*C₈H₁₂NS⁽¹⁺⁾ 
• 74-87-3 methylene chloride 
• 108-40-7 toluene-3-thiol 
• 123159-37-5 2,7-Dimethyl-9,10-dithia-4b,9a-diphospha-indeno[1,2-a]indene 

Relevant academic research and scientific papers

Synthesis of Aryl Methyl Sulfides from Arysulfonyl Chlorides with Dimethyl Carbonate as the Solvent and C1 Source

A new procedure for the synthesis of aryl methyl sulfides from dimethyl carbonate (DMC) and arylsulfonyl chlorides has been achieved. In this strategy, DMC plays a dual role as both, C1 building block and green solvent. Arylsulfonyl chlorides served as the sulfur precursors, and a variety of aryl methyl sulfides were obtained in moderate to excellent yields with good functional group tolerance. Additionally, alkylsulfonyl chloride and dibenzyl carbonate are proven to be suitable substrates as well.

Copper-Catalyzed Methylthiolation of Aryl Iodides and Bromides with Dimethyl Disulfide in Water

An efficient route to aryl methyl sulfides through the copper-catalyzed coupling reaction of aryl iodides or bromides with dimethyl disulfide in water is described. Electron-donating and electron-withdrawing functional groups in the substrates were tolerated, and the corresponding products were obtained in moderate to good yields.

Iridium-Catalyzed ortho-C-H Borylation of Thioanisole Derivatives Using Bipyridine-Type Ligand

A simple iridium catalytic system was developed that allows for a variety of 2-borylthioanisoles to be easily synthesized via ortho-selective C-H borylation of thioanisole derivatives. Once introduced, boryl and methylthio groups were converted by palladium-catalyzed transformations. Density functional theory calculations revealed that weak interactions, such as hydrogen bonding between the C-H bond of the SCH3 group and the oxygen atom of the boryl ligand, control the ortho-selectivity.

Reduction of CO2 with NaBH4/I2 for the Conversion of Thiophenols to Aryl Methyl Sulfides

We report a tandem reaction to realize reduction of carbon dioxide with thiophenols to generate aryl methyl sulfides under the NaBH4/I2 system with 18-crown-6 as the solvent. Thiophenols bearing electron-donating and electron-withdrawing groups are feasible in this reaction. Controlled experiment results indicate that 18-crown-6 plays a critical role in six-electron reduction of carbon dioxide.

Chemoenzymatic Deracemization of Chiral Sulfoxides

The highly enantioselective enzyme methionine sulfoxide reductase A was combined with an oxaziridine-type oxidant in a biphasic setup for the deracemization of chiral sulfoxides. Remarkably, high ee values were observed with a wide range of substrates, thus providing a practical route for the synthesis of enantiomerically pure sulfoxides.

IMIDAZOPYRIMIDINE COMPOUNDS USEFUL FOR THE TREATMENT OF CANCER

A compound of Formula (IA), or a pharmaceutically acceptable salt thereof, is provided that has been shown to be useful for treating a PRC2-mediated disease or disorder: wherein A, R3, R4, R6, and R7 are as defined herein.

Metal-Free, DTBP-Mediated Methylthiolation of Arylboronic Acids with Dimethyldisulfide

An efficient method for the C-S bond formation via the coupling reaction of arylboronic acids with dimethyldisulfide has been developed under the metal-free conditions. This novel protocol provides an attractive route for the synthesis of aryl methyl sulf

Rhodium-Catalyzed ipso-Borylation of Alkylthioarenes via C-S Bond Cleavage

Rhodium-catalyzed transformation of alkyl aryl sulfides into arylboronic acid pinacol esters via C-S bond cleavage is reported. In combination with transition-metal-catalyzed sulfanyl group-guided regioselective C-H borylation reactions of alkylthioarenes, this method allows the synthesis of a diverse range of multisubstituted arenes.

Palladium-Catalyzed ipso-Borylation of Aryl Sulfides with Diborons

A catalytic Miyaura-type ipso-borylation of aryl sulfides with diboron reagents has been achieved, providing arylboronate esters of synthetic use. The key conditions to transform inherently reluctant C-S bonds into C-B bonds include a palladium-NHC (N-heterocyclic carbene) precatalyst, bis(pinacolato)diboron, and lithium hexamethyldisilazide. This protocol is applicable to a reasonable range of aryl alkyl sulfides. Twofold borylation was observed in the reaction of diphenyl sulfide.

TRIAZOLOPYRIMIDINE COMPOUNDS AND USES THEREOF

A compound of Formula (I), or a pharmaceutically acceptable salt thereof, is provided that has been shown to be useful for treating a PRC2-mediated disease or disorder: wherein R1, R2, R3, R4, R5, and n are as defined herein.