Application In Synthesis of 3-Bromo-4-chloronitrobenzene. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 3-Bromo-4-chloronitrobenzene, is researched, Molecular C6H3BrClNO2, CAS is 16588-26-4, about Acid- and base-dependent hydrolysis of N-(sulfonatooxy)-3-bromoacetanilide: involvement of N-(3-bromophenyl)hydroxylamine O-sulfonate. Author is Novak, Michael; Rovin, Lise H.; Pelecanou, Maria; Mulero, Julio J.; Lagerman, Robert K..
The title compound (I) undergoes hydrolysis at 80° and 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 paths involve the hydrolysis of I to form N-(3-bromophenyl)hydroxylamine O-sulfonate (II). II cannot be directly detected under the conditions of this study, but its existence can be inferred from product study and trapping data. Although II undergoes decomposition entirely by heterolytic N-O bond cleavage to yield m-BrC6H4N+H (III), a less reactive analog of II, i.e., N-(3-bromophenyl)-O-pivaloylhydroxylamine (IV), apparently undergoes competitive homolytic and heterolytic N-O bond cleavage to yield both m-NHC6H4Br radical and III. Both II and IV serve as models for certain suspected carcinogenic metabolites of polycyclic aromatic amines and amides.
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