2905-24-0

Basic information

• Product Name: 3-Bromobenzenesulfonyl chloride
• Synonyms: BUTTPARK 94\57-33;3-BROMOBENZENE-1-SULFONYL CHLORIDE;3-BROMOBENZENESULFONYL CHLORIDE;3-BROMOBENZENESULPHONYL CHLORIDE;m-bromobenzenesulfonyl chloride;m-Bromobenzenesulfonyl;3-Bromobenzenesulfonyl chloride,98%;Benzenesulfonyl chloride, 3-broMo-
• CAS NO: 2905-24-0
• Molecular Formula: C₆H₄BrClO₂S
• Molecular Weight: 255.52
• EINECS: -0
• Product Categories: Benzenesulfonyl chloride;Miscellaneous;Aryl;Organohalides;Sulfonyl Chloride;Organic Building Blocks;Sulfonyl Halides;Sulfur Compounds;alkyl bromide| alkyl chloride
• Mol File: 2905-24-0.mol

Chemical Properties

• Melting Point: 31-33°C
• Boiling Point: 90-91 °C0.5 mm Hg(lit.)
• Flash Point: >110 °C
• Appearance: Clear colorless to yellow/Liquid
• Density: 1.773 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000909mmHg at 25°C
• Refractive Index: n20/D 1.593(lit.)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Sensitive: Moisture Sensitive
• BRN: 2691656
• CAS DataBase Reference: 3-Bromobenzenesulfonyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Bromobenzenesulfonyl chloride(2905-24-0)
• EPA Substance Registry System: 3-Bromobenzenesulfonyl chloride(2905-24-0)

Safety Data

• Hazard Codes: C,Xn
• Statements: 34-36/37/38-20/21/22
• Safety Statements: 26-36/37/39-45-36
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 2905-24-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Bromobenzenesulfonyl chloride is used as a synthetic intermediate for the development of N-sulfonylanthranilic acid derivatives and potent P1′ benzenesulfonyl azacyclic urea HIV protease inhibitors. These compounds are crucial in the ongoing research and development of new therapeutic strategies to combat HIV.
Used in Organic Synthesis:
In the field of organic chemistry, 3-bromobenzenesulfonyl chloride serves as a versatile building block for the preparation of various complex organic molecules. Some examples include:
1. 2-(3-bromophenyl)-5-n-butylfuran
2. 2-(3-bromophenyl)-3,6-dimethyl-4,5,6,7-tetrahydrobenzofuran
3. 3-bromo-4-(3-bromophenyl)thiophene
4. 2,5-bis(3-bromophenyl)-1-methylpyrrole
These synthesized compounds can be further utilized in the development of novel pharmaceuticals, advanced materials, or other specialty applications.

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

Upstream product

• 89862-26-0 3-bromobenzenesulfonyl hydrazide 
• 89598-96-9 (3-bromophenyl)boronic acid 
• 591-19-5 m-Bromoaniline 

Downstream Products

• 166338-06-3 N-phenyl-3-bromo-benzenesulfonamide 
• 848910-37-2 3-bromo-N-(4-fluorophenyl)benzene sulfonamide 
• 1159826-15-9 3-bromo-N,N-bis(2-hydroxyethyl)benzenesulfonamide 
• 871269-12-4 1-[(3-bromophenyl)sulfonyl]piperidine 
• 1286282-09-4 3-bromo-N-(2-(2-(pyrrolidin-1-yl)ethoxy))ethylbenzenesulfonamide trifluroacetic acid 
• 1286282-10-7 3-bromo-N-(5-morpholinopentyl)benzenesulfonamide trifluoroacetic acid 
• 1286282-11-8 3-bromo-N-(5-pyrrolidin-1-yl)pentylbenzenesulfonamide trifluoroacetic acid 
• 1286282-12-9 5-bromo-N-(5-(2-methyl)pyrrolidin-1-yl)pentylbenzenesulfonamide trifluoroacetic acid 
• 1286282-13-0 (S)-3-bromo-N-(5-(3-methyl)pyrrolidin-1-yl)pentylbenzenesulfonamide trifluoroacetic acid 
• 1286282-14-1 (S)-3-bromo-N-(5-(3-fluoro)pyrrolidin-1-yl)pentylbenzenesulfonamide trifluoroacetic acid 
• 1314241-36-5 3-bromo-N-(2-(2-(pyrrolidin-1-yl)ethoxy))ethylbenzenesulfonamide 
• 1314241-37-6 3-bromo-N-(5-morpholinopentyl)benzenesulfonamide 
• 1314241-38-7 3-bromo-N-(5-pyrrolidin-1-yl)pentylbenzenesulfonamide 
• 1314241-39-8 5-bromo-N-(5-(2-methyl)pyrrolidin-1-yl)pentylbenzenesulfonamide 

Relevant articles and documents

Facile synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazides

A simple and rapid method for efficient synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazide with NXS (X = Cl or Br) and late-stage conversion to several other functional groups was described. A variety of nucleophiles could be engaged in this transformation, thus permitting the synthesis of complex sulfonamides and sulfonates. In most cases, these reactions are highly selective, simple, and clean, affording products at excellent yields.

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.

Synthesis of aryl sulfonamides via palladium-catalyzed chlorosulfonylation of arylboronic acids

A palladium-catalyzed method for the preparation of sulfonamides is described. The process exhibits significant functional group tolerance and allows for the preparation of a number of arylsulfonyl chlorides and sulfonamides under mild conditions.

Discovery of a novel series of potent and orally bioavailable phosphoinositide 3-kinase γ inhibitors

The phosphoinositide 3-kinases (PI3Ks) have been linked to an extraordinarily diversified group of cellular functions making these enzymes compelling targets for the treatment of disease. A large body of evidence has linked PI3Kγ to the modulation of autoimmune and inflammatory processes making it an intriguing target for drug discovery. Our high-throughput screening (HTS) campaign revealed two hits that were nominated for further optimization studies. The in vitro activity of the first HTS hit, designated as the sulfonylpiperazine scaffold, was optimized utilizing structure-based design. However, nonoptimal pharmacokinetic properties precluded this series from further studies. An overlay of the X-ray structures of the sulfonylpiperazine scaffold and the second HTS hit within their complexes with PI3Kγ revealed a high degree of overlap. This feature was utilized to design a series of hybrid analogues including advanced leads such as 31 with desirable potency, selectivity, and oral bioavailability.

Polymer electrolyte and process for producing the same

A polymer electrolyte having, in a main chain, a structural unit represented by the following formula (1):-[Ar1-(SO2-N-(X+)-SO2-Ar2)m-SO2-N-(X+)-SO2-Ar1-O]- wherein Ar1 and Ar2 independently represent a divalent aromatic groups, m represents an integer of 0 to 3, and X+ represents an ion selected from hydrogen ion, an alkali metal ion and ammonium ion, which is excellent in proton conductivity, thermal resistance and strength. The polymer electrolyte is soluble in solvents and has excellent film forming property and recycling efficiency.