37891-95-5

Basic information

• Product Name: 1-(bromomethylsulfonyl)-4-methyl-benzene
• Synonyms: 1-(bromomethylsulfonyl)-4-methyl-benzene
• CAS NO: 37891-95-5
• Molecular Formula: C₈H₉BrO₂S
• Molecular Weight: 249.12
• Mol File: 37891-95-5.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 358.9°C at 760 mmHg
• Flash Point: 170.8°C
• Appearance: /
• Density: 1.55g/cm³
• Vapor Pressure: 5.11E-05mmHg at 25°C
• Refractive Index: 1.567
• CAS DataBase Reference: 1-(bromomethylsulfonyl)-4-methyl-benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(bromomethylsulfonyl)-4-methyl-benzene(37891-95-5)
• EPA Substance Registry System: 1-(bromomethylsulfonyl)-4-methyl-benzene(37891-95-5)

Safety Data

• Hazardous Substances Data: 37891-95-5(Hazardous Substances Data)

Usage

Description

1-(bromomethylsulfonyl)-4-methyl-benzene, also known as tosilate or 4-methylbenzenesulfonyl bromide, is a chemical compound derived from toluene with the molecular formula C8H9BrO2S. It is a sulfonyl bromide derivative characterized by its clear, colorless to light yellow liquid appearance and a strong, pungent odor. This highly reactive compound is known for its ability to participate in various chemical reactions such as nucleophilic substitution and deprotonation, making it a versatile reagent in organic synthesis. It is also utilized as a precursor for the development of pharmaceutical and agrochemical products. Due to its reactivity, it is classified as a hazardous substance and requires careful handling in well-ventilated areas with appropriate personal protective equipment.

Uses

Used in Organic Synthesis:
1-(bromomethylsulfonyl)-4-methyl-benzene is used as a reagent in organic synthesis for its ability to undergo nucleophilic substitution and deprotonation reactions, facilitating the creation of a wide range of chemical products.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1-(bromomethylsulfonyl)-4-methyl-benzene is used as a precursor for the development of various pharmaceutical products. Its reactivity allows for the synthesis of complex molecules needed in the formulation of different medications.
Used in Agrochemical Industry:
Similarly, in the agrochemical industry, 1-(bromomethylsulfonyl)-4-methyl-benzene is utilized as a starting material for the synthesis of compounds used in the development of pesticides and other agricultural chemicals, contributing to enhanced crop protection and yield.

InChI:InChI=1/C8H9BrO2S/c1-7-2-4-8(5-3-7)12(10,11)6-9/h2-5H,6H2,1H3

Upstream product

• 64-17-5 ethanol 
• 55490-03-4 bromo-(toluene-4-sulfonyl)-acetic acid amide 
• 141-52-6 sodium ethanolate 
• 3937-96-0 tosylacetic acid 
• 114245-60-2 (bromomethyl)(4-methylphenyl)sulfane 
• 925-90-6 ethylmagnesium bromide 
• 3185-99-7 Methyl p-tolyl sulfone 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 74-95-3 1,1-dibromomethane 
• 631-64-1 dibromoacetic acid 
• 26910-35-0 1-[(bromomethyl)-sulfinyl]-4-methylbenzene 
• 874009-27-5 1-bromo-1-(toluene-4-sulfonyl)-acetone 
• 23128-65-6 2-bromo-1-phenyl-2-(toluene-4-sulfonyl)ethanone 
• 5366-49-4 4-toluenesulfonylacetone 

Downstream Products

• 22952-14-3 1,2-bis(p-tolylsulfonyl)ethane 
• 3185-99-7 Methyl p-tolyl sulfone 
• 115909-66-5 C₂₃H₂₁N₃O₄S₂ 
• 129919-55-7 2--1,1a,2,3-tetrahydro-1-(p-tolylsulfonyl)azirino<1.2-a>quinoxaline 
• 54812-35-0 p-tolyl trichloromethyl sulfone 
• 54606-94-9 1-((1-bromopentyl)sulfonyl)-4-methylbenzene 
• 16212-08-1 1-methyl-4-[(E)-2-phenylethenesulfonyl]benzene 
• 54606-99-4 1-p-Tolylsulfonyl-1-brom-cyclopropan 
• 136613-52-0 1-Nitro-4-(toluene-4-sulfonylmethyl)-naphthalene 
• 136613-49-5 (1-Nitro-2-naphthyl)methyl 4-tolyl sulfone 
• 118684-46-1 2-nitro-3-(p-tolylsulfonylmethyl)bicyclo<4.4.1>undeca-1,3,5,7,9-pentaene 

Relevant articles and documents

Copper-Catalyzed Aerobic Oxidative Cleavage of Unstrained Carbon-Carbon Bonds of 1,1-Disubstituted Alkenes with Sulfonyl Hydrazides

Alkoxy radical-mediated carbon-carbon bond cleavages have emerged as a powerful strategy to complement traditional ionic-type transformations. However, carbon-carbon cleavage reaction triggered by alkoxy radical intermediate derived from the combination of alkyl radical and dioxygen, is scarce and underdeveloped. Herein, we report alkoxy radical, which was generated from alkyl radical and dioxygen, mediated selective cleavage of unstrained carbon-carbon bond for the oxysulfonylation of 1,1-disubstituted alkenes, providing facile access to a variety of valuable β-keto sulfones. Mechanistic experiments indicated alkoxy radical intermediate that underwent subsequent regioselective β-scission might be involved in the reaction and preliminary computational studies were conducted to provide a detailed explanation on the regioselectivity of the C—C bond cleavage. Notably, the strategy was successfully applied for constructing uneasily obtained architecturally intriguing molecules.

Chemoselective mono halogenation of β-keto-sulfones using potassium halide and hydrogen peroxide; synthesis of halomethyl sulfones and dihalomethyl sulfones

The synthesis of α-halo β-keto-sulfones using potassium halide and hydrogen peroxide as a chemoselective mono halogenation reagent and the synthesis of α,α-symmetrical and asymmetrical dihalo β-keto-sulfones and α-halo, α-alkyl and β-keto-sulfones is described. Base induced cleavage of α-halo β-keto-sulfones, α,α-dihalo β-keto-sulfones, and α-halo, α-alkyl β-keto-sulfones afforded the corresponding halomethyl sulfones, dihalomethyl sulfones and haloalkyl sulfones.