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

General 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 with a pungent smell. 3-Methylthioanisole is commonly used in the flavor and fragrance industry, where it is added to products such as perfumes, soaps, and cleaning agents to impart a sweet, earthy, and fruity aroma. It is also found naturally in foods and beverages such as beer, wine, coffee, and strawberries. Additionally, 3-Methylthioanisole may have potential applications in pharmaceuticals due to its ability to inhibit certain enzymatic activities. However, exposure to high concentrations of 3-Methylthioanisole can cause irritation to the eyes, skin, and respiratory system.

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 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 5188-07-8 sodium thiomethoxide 
• 33733-73-2 3-bromo-1-(methylthio)benzene 
• 624-92-0 Dimethyldisulphide 
• 28987-79-3 m-tolylmagnesium bromide 
• 1899-93-0 3-methylphenylsulfonyl chloride 
• 616-38-6 carbonic acid dimethyl ester 
• 625-95-6 3-Iodotoluene 
• 591-17-3 meta-bromotoluene 
• 124-38-9 carbon dioxide 
• 13150-71-5 (+/-)-methyl m-tolyl sulfoxide 
• 17933-03-8 m-tolylboronic acid 

Downstream Products

• 1657-89-2 (2,4-dinitro-phenyl)-(2-methyl-4-methylsulfanyl-phenyl)-diazene 
• 34786-24-8 ethyl 3-methylphenyl sulphide 
• 66794-12-5 (3-ethylphenyl)(methyl)sulfane 
• 105371-72-0 1-Ethylsulfanyl-2,3-dimethyl-benzene 
• 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 
• 54576-39-5 sec-butyl(m-tolyl)sulfane 
• 57847-76-4 S-Methyl-S-m-toluyl-N-p-tosylsulfylimin 
• 78644-77-6 N-(3-methylphenyl)pyridin-2-amine 
• 1205-64-7 3-Methyldiphenylamine 
• 99-04-7 m-Toluic acid 
• 253342-48-2 4,4,5,5-tetramethyl-2-m-tolyl-1,3,2-dioxaborolane 

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.

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.

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.