59662-65-6

Basic information

• Product Name: METHYLTHIOMETHYL P-TOLYL SULFONE
• Synonyms: METHYLTHIOMETHYL P-TOLYL SULPHONE;(Methylthiomethyl)(4-methylphenyl) sulfone;p-Tolyl(methylthiomethyl) sulfone;Tosylmethylmethyl sulfide;Methyl p-toluenesulfonylmethyl sulfate;Methylthiomethyl p-tolyl sulfo;Methylmercaptomethyl p-Tolyl Sulfone Methyl p-Toluenesulfonylmethyl Sulfide MT-sulfone;Methyl(tosylmethyl)sulfane
• CAS NO: 59662-65-6
• Molecular Formula: C₉H₁₂O₂S₂
• Molecular Weight: 216.32
• Product Categories: Sulfur Compounds (for Synthesis);Synthetic Organic Chemistry
• Mol File: 59662-65-6.mol
• Article Data: 5

Chemical Properties

• Melting Point: 82-85 °C(lit.)
• Boiling Point: 367.4°C at 760 mmHg
• Flash Point: 176°C
• Appearance: /
• Density: 1.215g/cm³
• Vapor Pressure: 2.9E-05mmHg at 25°C
• Refractive Index: 1.559
• CAS DataBase Reference: METHYLTHIOMETHYL P-TOLYL SULFONE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYLTHIOMETHYL P-TOLYL SULFONE(59662-65-6)
• EPA Substance Registry System: METHYLTHIOMETHYL P-TOLYL SULFONE(59662-65-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 13
• Hazardous Substances Data: 59662-65-6(Hazardous Substances Data)

Usage

General Description

Methylthiomethyl p-tolyl sulfone is an organic compound that belongs to the class of sulfones. It is a colorless to light yellow liquid with a pungent odor. This chemical is commonly used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. It is also utilized as a crosslinking agent in the production of polymers and adhesives. Methylthiomethyl p-tolyl sulfone is known for its high thermal stability, chemical inertness, and resistance to oxidation, making it a valuable compound in various industrial applications. However, it should be handled with caution as it may cause irritation to the eyes, skin, and respiratory system upon prolonged exposure.

InChI:InChI=1/C9H12O2S2/c1-8-3-5-9(6-4-8)13(10,11)7-12-2/h3-6H,7H2,1-2H3

Upstream product

• 64-17-5 ethanol 
• 858835-74-2 1-benzenesulfonyl-1-methylsulfanyl-acetone 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 856343-92-5 1-methylsulfanyl-1-(toluene-4-sulfonyl)-acetone 
• 67-56-1 methanol 
• 119555-54-3 3-Benzyloxy-1-methylsulfanyl-1-(toluene-4-sulfonyl)-propan-2-one 
• 119555-60-1 1-Methylsulfanyl-4-phenyl-1-(toluene-4-sulfonyl)-butan-2-one 
• 2949-92-0 methanethiosulfonic acid S-methyl ester 
• 31378-03-7 1-phenyl-2-tosylethanone 
• 2373-51-5 chloro-methylsulfanyl-methane 
• 16437-69-7 (methylthio)methyl acetate 
• 657-84-1 sodium tosylate 
• 68305-26-0 S-methyl p-chlorobenzenethiosulfonate 
• 7569-26-8 chloromethyl p-tolylsulfone 

Downstream Products

• 64399-25-3 (Methylsulfonyl)methyl p-Tolyl Sulfone 
• 107535-97-7 2-[2-Methylsulfanyl-2-(toluene-4-sulfonyl)-ethyl]-[1,3]dioxolane 
• 87228-75-9 2-methylthio-1-(2-thienyl)-2-(p-tolylsulfonyl)ethene 
• 98223-60-0 2-[5-Methylsulfanyl-5-(toluene-4-sulfonyl)-pentyloxy]-tetrahydro-pyran 
• 87228-72-6 1-Methanethio-1-toluenesulphonylcyclpentane 
• 120-92-3 cyclopentanone 
• 107536-00-5 1-Methylsulfanyl-4-phenyl-1-(toluene-4-sulfonyl)-butan-2-ol 
• 122277-45-6 1-Methyl-4-(1-methylsulfanyl-pent-4-ene-1-sulfonyl)-benzene 
• 110036-01-6 2-p-tolylsulfonylmethylquinoline 1-oxide 
• 110064-35-2 2-(methylthio-p-tolylsulfonyl)methylquinoline 1-oxide 
• 94816-47-4 1-(methylthio)-1-propyl p-tolyl sulfone 
• 162777-19-7 <(4-methylphenyl)sulfonyl>(trimethylsilyl)methyl methyl sulfide 
• 162777-24-4 Z-1,2-bis(4-methylphenylsulfonyl)-1,2-bis(methylthio)-ethylene 
• 87228-71-5 1-Methyl-4-(1-methylsulfanyl-cyclohexanesulfonyl)-benzene 

Relevant articles and documents

Donor substituted sulfonyl carbenes, 2: Organothio sulfonyl carbenes

Organothio sulfonyl carbenes 3 have been generated via ylid thermolysis or via α-elimination starting from α-chloro α-organothio sulfones and their derivatives. They have been captured by suitable nucleophilic trapping reagents (diazomethane, enol ethers, and other). Their nucleophilic carbenoid precursors could be trapped by an electrophilic olefin (ketene dithioacetal S,S-dioxides as Michael acceptors). Stable carbene Z-dimers could be obtained under various conditions. Bromine catalyzed isomerization to E-isomers proved to be reversible.

UTILIZATION OF METHYLTHIOMETHYL p-TOLYL SULFONE IN ORGANIC SYNTHESIS

Methylthiomethyl p-tolyl sulfone was found to be one of the useful reagents for preparation of various organic compounds such as S-methyl α-ketocarbothioates, carboxylic esters, five- and six-membered cycloalkanones, and α-methoxy-α-arylacetic esters.

A NOVEL ROUTE FROM A CARBOXYLIC ACID TO A CARBALDEHYDE USING METHYLTHIOMETHYL p-TOLYL SULFONE

A new conversion of a carboxylic ester to a carbaldehyde involing formation and dissociation of a C-C bond at the acyl carbon was accomplished by the use of methylthiomethyl p-tolyl sulfone (1).