20964-31-2

Upstream product

• 99-65-0 meta-dinitrobenzene 
• 13331-27-6 m-nitrobenzene boronic acid 
• 97-02-9 2,4-Dinitroanilin 
• 610-31-1 1,2,4-trinitrobenzene 
• 585-79-5 m-nitrobromobenzene 

Downstream Products

• 860682-14-0 N,N-bis-(3-nitro-phenyl)-benzamide 
• 105391-34-2 3,3'-dinitrotriphenylamine 
• 861525-32-8 bis-(5-amino-2-bromo-phenyl)-methane 
• 500294-00-8 bis-(3-acetylamino-phenyl)-methane 
• 861613-57-2 bis-(5-acetylamino-2-bromo-phenyl)-methane 
• 860681-27-2 N,N-bis-(3-amino-phenyl)-benzamide 
• 219853-08-4 (3,3'-bisamino)diphenylamine 
• 19471-12-6 3,3'-methylenedianiline 

Relevant academic research and scientific papers

The use of hydroxylamine hydrochloride in the Chan-Lam reaction: A simple access to symmetric diarylamines

A CuBr-catalyzed coupling reaction of hydroxylamine hydrochloride and arylboronic acids is described, providing a simple and efficient methodology for the synthesis of symmetric diaryl amines. The reaction shows good functional group tolerance. Georg Thie

The Reaction of Nitrobenzenes with Sodium Borohydride; a Novel Reductive Coupling to Diphenylamine Derivatives

The reduction of mono-, di-, and trinitro-substituted benzenes by NaBH4 in hydroxylic solvents gives very different products depending on structure and reaction conditions.In addition to known reactions, such as formation of azoxybenzene and azobenzene derivatives, displacement of nitro groups by hydrogen, and ring reduction, a novel coupling reaction with loss of one nitro group was observed.From 1,3-dinitrobenzene and 1,3,5-trinitrobenzene, diphenylamine derivatives were obtained in reactions that are clean and of preparative value when the nitro compound is present in exess.From 1,2-dinitrobenzene the diphenylhydroxylamine derivative was obtained in a much slower, but equally clean reaction.Possible mechanisms are discussed, and an aromatic ipso radical substitution of a nitro group by a phenylnitroxide intermediate is proposed.