6656-59-3

Basic information

• Product Name: Benzoic acid 3-bromo-2-oxopropyl ester
• Synonyms: Benzoic acid 3-bromo-2-oxopropyl ester
• CAS NO: 6656-59-3
• Molecular Formula: C₁₀H₉BrO₃
• Molecular Weight: 257.0807
• Mol File: 6656-59-3.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 365.4°Cat760mmHg
• Flash Point: 174.8°C
• Appearance: /
• Density: 1.506g/cm³
• Vapor Pressure: 1.57E-05mmHg at 25°C
• Refractive Index: 1.558
• CAS DataBase Reference: Benzoic acid 3-bromo-2-oxopropyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid 3-bromo-2-oxopropyl ester(6656-59-3)
• EPA Substance Registry System: Benzoic acid 3-bromo-2-oxopropyl ester(6656-59-3)

Safety Data

• Hazardous Substances Data: 6656-59-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H9BrO3/c11-6-9(12)7-14-10(13)8-4-2-1-3-5-8/h1-5H,6-7H2

Upstream product

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Relevant articles and documents

Bioactivation of 6,7-dimethyl-2,4-di-1-pyrrolidinyl-7H-pyrrolo[2,3- d]pyrimidine (U-89843) to reactive intermediates that bind covalently to macromolecules and produce genotoxicity

U-89843 is a novel pyrrolo[2,3-d]pyrimidine antioxidant with prophylactic activity in animal models of lung inflammation. During preclinical safety evaluation, U-89843 was found to give a positive response in the in vitro unscheduled DNA synthesis (UDS) assay, an assay which measures DNA repair following chemically-induced DNA damage in metabolically competent rat hepatocytes. Incubation of [14C]U-89843 with liver microsomes resulted in covalent binding of radioactive material to macromolecules by a process that was NADPH-dependent. U-89843 has been shown to undergo C-6 methylhydroxylation to give U-97924, in rat both in vivo and in vitro, in a reaction catalyzed by cytochrome P450 2C11. Synthetical U-97924 is chemically reactive and undergoes dimerization in aqueous solution. The dimerization of U-97924 was significantly inhibited by addition of nucleophiles such as methanol, glutathione, and N-acetylcysteine. Characterization of the corresponding methanol, glutathione, and N-acetylcysteine adducts of U-97924 supported the hypothesis of a reaction pathway involving reactive iminium species formed via dehydration of U-97924. The metabolism-dependent irreversible covalent binding of radioactive material to liver microsomal protein and DNA also is dramatically reduced in the presence of reduced glutathione (GSH). A trifluoromethyl analog of U-89843 was prepared in an effort to block the corresponding metabolic hydroxylation pathway. This new compound (U-107634) was found to be negative in the in vitro UDS assay, and its metabolic susceptibility toward hydroxylation at the C-6 methyl group was eliminated. These observations suggest that the positive in vitro UDS results of U-89843 are mediated by the bioactivation of U-89843, leading to reactive electrophilic intermediates derived from the (hydroxymethyl)pyrrole metabolite U-97924.