2905-25-1

Basic information

• Product Name: 2-Bromobenzenesulphonyl chloride
• Synonyms: 2-BROMOSULFONYL CHLORIDE;2-BROMOBENZENE-1-SULFONYL CHLORIDE;2-BROMOBENZENESULFONYL CHLORIDE;2-BROMOBENZENESULPHONYL CHLORIDE;O-BROMOBENZENESULFONYL CHLORIDE;Benzenesulfonyl chloride, 2-bromo-;2-bromobeneze sulfonyl chloride;2-Bromobenzenesulfonyl
• CAS NO: 2905-25-1
• Molecular Formula: C₆H₄BrClO₂S
• Molecular Weight: 255.52
• Product Categories: blocks;Bromides;Sulfonamides;Phenyls & Phenyl-Het;Sulphonyl Chlorides;Benzenesulfonyl chloride;Sulfonyl Chloride;Aryl;Organohalides;Phenyls & Phenyl-Het;Sulphonyl Chlorides;Organic Building Blocks;Sulfonyl Halides;Sulfur Compounds
• Mol File: 2905-25-1.mol
• Article Data: 11

Chemical Properties

• Melting Point: 49-52 °C(lit.)
• Boiling Point: 98-100°C (0.5 torr)
• Flash Point: 127-128°C/2.4mm
• Appearance: Slightly yellow/Crystalline Powder
• Density: 1.7910 (estimate)
• Vapor Pressure: 0.000974mmHg at 25°C
• Refractive Index: 1.591
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Sensitive: Moisture Sensitive
• BRN: 2692202
• CAS DataBase Reference: 2-Bromobenzenesulphonyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromobenzenesulphonyl chloride(2905-25-1)
• EPA Substance Registry System: 2-Bromobenzenesulphonyl chloride(2905-25-1)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-27-36/37/39-45
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 2905-25-1(Hazardous Substances Data)

Usage

Description

2-Bromobenzenesulphonyl chloride is a slightly yellow crystalline powder that can be synthesized from 2-aminobenzenesulfonic acid. It is a chemical compound with a bromine atom attached to a benzene ring, which is connected to a sulfonyl chloride group. 2-Bromobenzenesulphonyl chloride is known for its reactivity and is commonly used in various chemical reactions and syntheses.

Uses

Used in Pharmaceutical Industry:
2-Bromobenzenesulphonyl chloride is used as a reagent for the preparation of 2-bromobenzenesulfonic acid phenyl ester, which is an important intermediate in the synthesis of various pharmaceutical compounds. The application reason is its ability to facilitate the formation of the desired ester through a straightforward reaction process.
Used in Chemical Synthesis:
In the chemical synthesis industry, 2-Bromobenzenesulphonyl chloride is used as a reactant for the sufonylation during the synthesis of 2-bromobenzenesulfonamide. The application reason is its reactivity, which allows for the formation of the desired amide compound through a sufonylation reaction.
Used in Chiral Compound Synthesis:
2-Bromobenzenesulphonyl chloride is also used in the synthesis of chiral 2-(p-toluenesulfinyl)benzenesulfonamide, which is an important chiral auxiliary in asymmetric synthesis. The application reason is its ability to provide the necessary chiral environment for the formation of the desired chiral compound, which can be used in various enantioselective reactions.

InChI:InChI=1/C6H4BrClO2S/c7-5-3-1-2-4-6(5)11(8,9)10/h1-4H

Upstream product

• 146335-10-6 1-bromo-2-<(methoxymethyl)thio>benzene 
• 615-36-1 2-bromoaniline 
• 244205-40-1 (2-bromophenyl)boronic acid 
• 108-86-1 bromobenzene 
• 88-21-1 2-amino-1-benzenesulfonic acid 
• 576-92-1 bromobenzene-2-sulfonic acid 
• 10448-07-4 2-bromobenzenediazonium tetrafluoroborate 

Downstream Products

• 5324-79-8 1-bromo-2-(phenylsulfonyl)benzene 
• 90725-81-8 2-bromo-N-(5-methyl-[1,3,4]oxadiazol-2-yl)-benzenesulfonamide 
• 93307-15-4 2-bromo-N-(5-pentyl-[1,3,4]thiadiazol-2-yl)-benzenesulfonamide 
• 139021-59-3 1-(2-bromobenzenesulfonyl)-2,5-dihydro-1H-pyrrole 
• 139021-56-0 1-(2'-bromobenzenesulphonyl)-1,2,5,6-tetrahydropyridine 
• 150256-95-4 N-<(4-bromophenyl)methyl>-2-bromobenzenesulfonamide 
• 92748-09-9 2-bromobenzene-1-sulfonamide 
• 153623-86-0 N-(3,4-Dimethyl-5-isoxazolyl)-2-bromo-benzenesulfonamide 
• 153624-58-9 1-((2-bromophenyl)sulfonyl)-1H-pyrrole 
• 138733-50-3 N-(1,1-dimethylethyl)-2-bromobenzenesulfonamide 
• 219945-37-6 2-bromobenzenesulfonic acid isopropyl ester 
• 1026810-59-2 2-(2-bromo-benzenesulfonylamino)-3-tert-butoxycarbonylamino-propionic acid methyl ester 
• 440352-77-2 2-(2-bromobenzenesulfonyl)-4,5-dichloropyridazin-3-one 
• 195447-72-4 N-(4,5-dimethyl-3-isoxazolyl)-2-bromobenzenesulfonamide 

Relevant articles and documents

Nickel-Catalyzed One-Pot Carbonylative Synthesis of 2-Mono- And 2,3-Disubstituted Thiochromenones from 2-Bromobenzenesulfonyl Chlorides and Alkynes

A nickel-catalyzed one-pot carbonylation reaction of 2-bromobenzenesulfonyl chlorides with alkynes for the synthesis of thiochromenones has been established. Both terminal and internal alkynes were suitable substrates in this carbonylative transformation, and a broad range of 2-mono- and 2,3-disubstituted thiochromenone products were obtained in moderate to good yields with quite high functional group compatibility. Notably, this procedure presents the first example of nickel-catalyzed carbonylative synthesis of thiochromenones with 2-bromobenzenesulfonyl chlorides as a promising sulfur precursor.

Aromatic Chlorosulfonylation by Photoredox Catalysis

Visible-light photoredox catalysis enables the efficient synthesis of arenesulfonyl chlorides from anilines. The new protocol involves the convenient in situ preparation of arenediazonium salts (from anilines) and the reactive gases SO2and HCl (from aqueous SOCl2). The photocatalytic chlorosulfonylation operates at mild conditions (room temperature, acetonitrile/water) with low catalyst loading. Various functional groups are tolerated (e.g., halides, azides, nitro groups, CF3, SF5, esters, heteroarenes). Theoretical and experimental studies support a photoredox-catalysis mechanism.

Palladium-catalysed dehydrogenative sp3 C-H bonds functionalisation into alkenes: A direct access to N-alkenylbenzenesulfonamides

The palladium-catalysed dehydrogenation of sp3 carbon-hydrogen bonds of N-alkylbenzenesulfonamides allows a simple access to N-alkenylbenzenesulfonamides. The reaction proceeds with easily accessible catalysts, with pivalate as a base, and allo