77421-13-7

Basic information

• Product Name: (2-CHLORO-PHENYL)-METHANESULFONYL CHLORIDE
• Synonyms: (2-CHLORO-PHENYL)-METHANESULFONYL CHLORIDE;S26;S30;S36/37/39;S45;(2-Chlorophenyl)methanesulfonyl chloride, 2-Chloro-α-toluenesulfonyl chloride, 2-Chlorobenzenemethanesulfonyl chloride;2-Chlorobenzylsulfonyl chloride;(2-Chlorophenyl)methanesulfonyl chloride ,97%
• CAS NO: 77421-13-7
• Molecular Formula: C₇H₆Cl₂O₂S
• Molecular Weight: 225.09
• Mol File: 77421-13-7.mol
• Article Data: 15

Chemical Properties

• Melting Point: 60 °C
• Boiling Point: 321.2 °C at 760 mmHg
• Flash Point: 148 °C
• Appearance: /
• Density: 1.499 g/cm³
• Vapor Pressure: 0.000569mmHg at 25°C
• Refractive Index: 1.578
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (2-CHLORO-PHENYL)-METHANESULFONYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (2-CHLORO-PHENYL)-METHANESULFONYL CHLORIDE(77421-13-7)
• EPA Substance Registry System: (2-CHLORO-PHENYL)-METHANESULFONYL CHLORIDE(77421-13-7)

Safety Data

• Hazard Codes: Xi,C,Xn
• Statements: 34-29-14-41-37/38-22
• Safety Statements: 26-36/37/39-39-45
• RIDADR: 3261
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 77421-13-7(Hazardous Substances Data)

Usage

General Description

(2-Chloro-phenyl)-methanesulfonyl chloride, also known as mesyl chloride, is a chemical compound that is used as a reagent in various organic synthesis processes. It is a colorless liquid with a pungent odor, and it is highly reactive. Mesyl chloride is widely used in the pharmaceutical industry for the production of various drugs, as well as in the synthesis of polymers and dyes. It is also a key intermediate in the preparation of sulfonamides and other functionalized organic compounds. Mesyl chloride is known to be corrosive and dangerous if not handled properly, and it should be used with caution in a well-ventilated environment and with appropriate protective equipment.

InChI:InChI=1/C7H6Cl2O2S/c8-7-4-2-1-3-6(7)5-12(9,10)11/h1-4H,5H2

Upstream product

• 611-19-8 1-chloro-2-(chloromethyl)benzene 
• 73183-34-3 bis(pinacol)diborane 
• 611-17-6 1-bromomethyl-2-chlorobenzene 
• 41345-36-2 Sodium 2-chlorobenzylsulphonate 
• 3778-85-6 2-chlorophenylmethyl carbamimidothioate hydrochloride 

Downstream Products

• 1292292-16-0 2-[(2-chlorophenyl)methyl]succinic acid dimethyl ester 
• 1296730-84-1 C₁₇H₁₄ClN₃O₃S 

Relevant articles and documents

Para-Selective C-H Borylation of Common Arene Building Blocks Enabled by Ion-Pairing with a Bulky Countercation

The selective functionalization of C-H bonds at the arene para position is highly challenging using transition metal catalysis. Iridium-catalyzed borylation has emerged as a leading technique for arene functionalization, but there are only a handful of strategies for para-selective borylation, which operate on specific substrate classes and use bespoke ligands or catalysts. We describe a remarkably general protocol which results in para-selectivity on some of the most common arene building blocks (anilines, benzylamines, phenols, benzyl alcohols) and uses standard borylation ligands. Our strategy hinges upon the facile conversion of the substrates into sulfate or sulfamate salts, wherein the anionic arene component is paired with a tetrabutylammonium cation. We hypothesize that the bulk of this cation disfavors meta-C-H borylation, thereby promoting the challenging para-selective reaction.

Rhodium-Catalyzed meta-C?H Functionalization of Arenes

Rhodium-catalyzed ortho-C?H functionalization is well known in the literature. Described herein is the Xphos-supported rhodium catalysis of meta-C?H olefination of benzylsulfonic acid and phenyl acetic acid frameworks with the assistance of a para-methoxy-substituted cyano phenol as the directing group. Complete mono-selectivity is observed for both scaffolds. A wide range of olefins and functional groups attached to arene are tolerated in this protocol.

Tert -Butyl Hypochlorite Mediated Oxidative Chlorination of S -Alkylisothiourea Salts: Synthesis of Sulfonyl Chlorides

Under neutral conditions, a variety of S-alkylisothiourea salts were smoothly converted into the corresponding sulfonyl chlorides through tert-butyl chlorite mediated oxidative chlorination in good to excellent yields after simple purification. In addition to the environmental and procedural advantages of this method, the neutral conditions potentially make it applicable to substrates that bear acid-sensitive functional groups. For example, the Cbz-protected 2-aminoethanesulfonyl chloride could be synthesized in moderate to good yields under the current neutral conditions, and the acid-sensitive Cbz-protecting group was not affected.