5302-76-1

Basic information

• Product Name: dibromoacetyl chloride
• Synonyms: dibromoacetyl chloride;Einecs 226-148-8
• CAS NO: 5302-76-1
• Molecular Formula: C₂HBr₂ClO
• Molecular Weight: 236.28974
• EINECS: 226-148-8
• Mol File: 5302-76-1.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 161.8°Cat760mmHg
• Flash Point: 51.7°C
• Appearance: /
• Density: 2.441g/cm³
• Vapor Pressure: 2.23mmHg at 25°C
• Refractive Index: 1.566
• CAS DataBase Reference: dibromoacetyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: dibromoacetyl chloride(5302-76-1)
• EPA Substance Registry System: dibromoacetyl chloride(5302-76-1)

Safety Data

• Hazardous Substances Data: 5302-76-1(Hazardous Substances Data)

Usage

Description

Dibromoacetyl chloride is an organic compound with the chemical formula C2HBr2ClO, characterized by its reactivity and use as an intermediate in various chemical syntheses. It is a halogenated derivative of acetyl chloride, featuring two bromine atoms and one chlorine atom attached to the carbonyl group.

Uses

Used in Chemical Synthesis:
Dibromoacetyl chloride is used as an intermediate in the synthesis of Bromochloroacetamide (B740048), a haloacetemide byproduct. dibromoacetyl chloride is relevant in the context of water purification, as it is formed during the use of nitrogenous disinfection agents at water purification plants in European and Asian countries. The production and monitoring of such byproducts are essential for ensuring the safety and quality of water supplies.

InChI:InChI=1/C2HBr2ClO/c3-1(4)2(5)6/h1H

Upstream product

• 631-64-1 dibromoacetic acid 

Downstream Products

• 100116-29-8 1-dibromoacetyl-4-phenyl-piperazine 
• 26346-88-3 Dibromo-acetic acid phenyl ester 
• 93017-46-0 α,α'-Bis-(ethyl-dibromacetyl-amino)-p-xylol 
• 97638-29-4 2-Chlor-α,α'-bis-(ethyl-dibromacetyl-amino)-p-xylol 
• 54304-86-8 8-Fluoro-1-(dibromomethyl)-6-(o-chlorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine 
• 1361557-26-7 4-oxo-cyclohexyl dibromoacetate 

Relevant articles and documents

Microsomal oxidation of tribromoethylene and reactions of tribromoethylene oxide.

Halogenated olefins are of interest because of their widespread use in industry and their potential toxicity to humans. Epoxides are among the enzymatic oxidation products and have been studied in regard to their toxicity. Most of the attention has been given to chlorinated epoxides, and we have previously studied the reactions of the mono-, di-, tri-, and tetrachloroethylene oxides. To further test some hypotheses concerning the reactivity of these compounds, we prepared tribromoethylene (TBE) oxide and compared it to trichloroethylene (TCE) oxide and other chlorinated epoxides. TBE oxide reacted with H(2)O about 3 times faster than did TCE oxide. Several hydrolysis products of TBE oxide were the same as formed from TCE oxide, i.e., glyoxylic acid, CO, and HCO(2)H. Br(2)CHCO(2)H was formed from TBE oxide; the yield was higher than for Cl(2)CHCO(2)H formed in the hydrolysis of TCE oxide. The yield of tribromoacetaldehyde was 0.4% in aqueous buffer (pH 7.4). In rat liver microsomal incubations containing TBE and NADPH, Br(2)CHCO(2)H was a major product, and tribromoacetaldehyde was a minor product. These results are consistent with schemes previously developed for halogenated epoxides, with migration of bromine being more favorable than for chlorine. Reaction of TBE oxide with lysine yielded relatively more N-dihaloacetyllysine and less N-formyllysine than in the case of TCE oxide. This same pattern was observed in the products of the reaction of TBE oxide with the lysine residues in bovine serum albumin. We conclude that the proposed scheme of hydrolysis of halogenated epoxides follows the expected halide order and that this can be used to rationalize patterns of hydrolysis and reactivity of other halogenated epoxides.