4886-77-5

Basic information

• Product Name: 3-Methylthioanisole
• Synonyms: 1-Methyl-3-(methylthio)benzene;1-Methyl-3-methylsulfanylbenzene;3-Methylthioanisole;methyl(m-tolyl)sulfane;1-(Methylthio)-3-methylbenzene;3-Methylthiotoluene;Methyl 3-methylphenyl sulfide;Methyl m-tolyl sulfide
• CAS NO: 4886-77-5
• Molecular Formula: C₈H₁₀S
• Molecular Weight: 138.23
• Mol File: 4886-77-5.mol
• Article Data: 24

Chemical Properties

• Melting Point: 84 °C
• Boiling Point: 203.67°C (estimate)
• Flash Point: 73.6 °C
• Appearance: /
• Density: 1.0260
• Vapor Pressure: 0.478mmHg at 25°C
• Refractive Index: 1.5731
• CAS DataBase Reference: 3-Methylthioanisole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methylthioanisole(4886-77-5)
• EPA Substance Registry System: 3-Methylthioanisole(4886-77-5)

Safety Data

• Hazardous Substances Data: 4886-77-5(Hazardous Substances Data)

Usage

Description

3-Methylthioanisole, also known as 3-methyl-4-methoxythiophenol, is an organic compound with the formula C9H10OS. It is a colorless to pale yellow liquid characterized by a pungent smell. 3-Methylthioanisole is recognized for its natural presence in various foods and beverages, contributing to their distinct aroma profiles.

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

• 1899-93-0 3-methylphenylsulfonyl chloride 
• 616-38-6 carbonic acid dimethyl ester 
• 624-92-0 Dimethyldisulphide 
• 625-95-6 3-Iodotoluene 
• 591-17-3 meta-bromotoluene 
• 108-40-7 toluene-3-thiol 
• 124-38-9 carbon dioxide 
• 13150-71-5 (+/-)-methyl m-tolyl sulfoxide 
• 17933-03-8 m-tolylboronic acid 
• 74-88-4 methyl iodide 
• 67-68-5 dimethyl sulfoxide 
• 28987-79-3 m-tolylmagnesium bromide 
• 33733-73-2 3-bromo-1-(methylthio)benzene 
• 5188-07-8 sodium thiomethoxide 

Downstream Products

• 57847-76-4 S-methyl-S-(3-tolyl)-N-(p-tolylsulfonyl)sulfimide 
• 57847-76-4 S-methyl-S-(3-tolyl)-N-(p-tolylsulfonyl)sulfimide 
• 22132-98-5 imino(methyl)(3-methylphenyl)-λ⁶-sulfanone 
• 1205-64-7 3-Methyldiphenylamine 
• 451524-41-7 6-methyl-benzo[b]thiophen-3-ol 
• 502484-70-0 2-chloro-1-(2-methyl-4-methylsulfanyl-phenyl)-ethanone 
• 35657-16-0 3-methylphenyl chloromethyl sulfide 
• 13150-71-5 (+/-)-methyl m-tolyl sulfoxide 
• 10355-06-3 methyl 3-methylphenyl sulfone 
• 17796-88-2 N-[(3-methylphenyl)thio]succinimide 
• 90532-02-8 1-bromo-2-methyl-4-methylsulfanylbenzene 
• 1657-89-2 (2,4-dinitro-phenyl)-(2-methyl-4-methylsulfanyl-phenyl)-diazene 
• 57847-76-4 S-Methyl-S-m-toluyl-N-p-tosylsulfylimin 
• 78644-77-6 N-(3-methylphenyl)pyridin-2-amine 

Relevant articles and documents

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.

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.