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

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

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

Downstream Products

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

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.

Solvolysis of N-Sulfonoxyacetanilides in Aqueous and Alcohol Solutions: Generation of Electrophilic Species

A series of ring-substituted N-sulfonoxyacetanilides (1a-f) were synthesized, and their solvolysis reactions in aqueous and alcohol solvents were studied.These compounds serve as models for the carcinogenic metabolites of polynuclear aromatic amides.Kinetic and product studies yielded evidence for solvolysis via N-O bond cleavage in aqueous solution with generation of tight ion pairs and solvent-separated ion pairs.The tight ion pairs, which cannot be trapped by nucleophiles or reducing agents, give rise to o-sulfonoxyacetanilides, while the solvent-separated ion pairs can be trapped by these reagents to yield ring-substituted compounds and reduction products.The para-substituted N-sulfonoxyacetanilides yield substantial amounts of highly electrophilic p-benzoquinone imine derivatives such as 10 during solvolysis in aqueous media.In ethanol these esters solvolyze exclusively via S-O bond cleavage with apparent production of SO3.This study demonstrates that electrophilic species other than nitrenium ions can be generated during the solvolysis of N-sulfonoxy-N-arylamides.These species may play a role in the in vivo activity of these metabolites.