38373-20-5

Basic information

• Product Name: N-(3-bromophenyl)-N-hydroxyacetamide
• Synonyms: Acetamide, N-(3-bromophenyl)-N-hydroxy-; N-(3-Bromophenyl)-N-hydroxyacetamide
• CAS NO: 38373-20-5
• Molecular Formula: C₈H₈BrNO₂
• Molecular Weight: 230.0586
• Mol File: 38373-20-5.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 340.8°C at 760 mmHg
• Flash Point: 159.9°C
• Density: 1.664g/cm³
• Vapor Pressure: 3.24E-05mmHg at 25°C
• Refractive Index: 1.64
• CAS DataBase Reference: N-(3-bromophenyl)-N-hydroxyacetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(3-bromophenyl)-N-hydroxyacetamide(38373-20-5)
• EPA Substance Registry System: N-(3-bromophenyl)-N-hydroxyacetamide(38373-20-5)

Safety Data

• Hazardous Substances Data: 38373-20-5(Hazardous Substances Data)

Upstream product

• 91631-57-1 N-(sulfonatooxy)-3-bromoacetanilide 
• 114838-63-0 C₈H₈BrNO₂ 
• 13125-68-3 1-bromo-3-nitrosobenzene 
• 431-03-8 dimethylglyoxal 
• 24171-78-6 m-bromophenylhydroxylamine 
• 75-36-5 acetyl chloride 

Downstream Products

• 91631-58-2 N-sulfonoxy-m-bromoacetanilide pyridinium salt 
• 81375-86-2 C₈H₇BrNO₂ 
• 114838-66-3 N'-(3-Bromo-phenyl)-N-methyl-N-phenyl-hydrazine 
• 114838-65-2 N'-(3-Bromo-phenyl)-N,N-diethyl-hydrazine 

Relevant articles and documents

Catalyst-free generation of acyl radicals induced by visible light in water to construct C-N bonds

We describe herein a catalyst-free and redox-neutral photochemical strategy for the direct generation of acyl radicals from α-diketones, and its selective conversion of nitrosoarenes to hydroxyamides or amides with AcOH or NaCl as an additive. The reaction was carried out under mild conditions in water with purple LEDs as the light source. A broad scope of substrates was demonstrated. Mechanistic experiments indicate that α-diketones cleave to give acyl radicals, with hydroxyamides being further reduced to amides.

Acid- and Base-Dependent Hydrolysis of N-(Sulfonatooxy)-3-bromoacetanilide: Involvement of N-(3-Bromophenyl)hydroxylamine-O-sulfonate

N-(Sulfonatooxy)-3-bromoacetanilide (1e) undergoes hydrolysis at 80 deg C in the range pH 1.0-8.0 by acid- and base-dependent processes and by an uncatalyzed path.The uncatalyzed reaction exhibits the same characteristics as the uncatalyzed N-O bond-cleavage reactions of the more reactive N-(sulfonatooxy)acetanilides.The pH-dependent pathways involve the hydrolysis of 1e to form N-(3-bromophenyl)hydroxylamine-O-sulfonate (2).This material cannot be directly detected under the conditions of this study, but its existence can be inferred from product study and trapping data.Although 2 undergoes decomposition entirely by heterolytic N-O bond cleavage to yield nitrenium ion intermediate 14, a less reactive analogue of 2, N-(3-bromophenyl)-O-pivaloylhydroxylamine (4), apparently undergoes competitive homolytic and heterolytic N-O bond cleavage to yield both the arylamino radical 17 and the nitrenium ion 14.Both 2 and 4 serve as models for certain suspected carcinogenic metabolites of polycyclic aromatic amines and amides.