US EPA

8222300 

Journal Article 

Derivatives of 1:2:4:5-tetrachlorobenzene. Part I. Nitro- and amino-compounds 

Peters, AT; Rowe, FM; Stead, DM 

1943 

Yes 

Journal of the Chemical Society
ISSN: 0368-1769 

233-235 

English 

10.1039/jr9430000233 

https://www.scopus.com/inward/record.uri?eid=2-s2.0-4243359735&doi=10.1039%2fjr9430000233&partnerID=40&md5=4df432753a2dbedcfb7153c350ba0400
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2:3:5:6-Tetrachloro-4-nitroaniline (IV), prepared from 2:3:5:6-tetrachloro- l:4-dinitrobenzene (III) by reduction with sodium hydrosulphite or by amination with alcoholic ammonia, is diazotisable with nitrosylsulphuric acid at 60-70° and then couples to form azo-dyes. 2:3:5:6-Tetrachloro- aniline, -1:4-diamino-benzene, and -4-aminoanisole were also examined as intermediates for azo-dyes. 2:3:5:6-Tetrachloro-4-nitrophenol (V), best prepared by nitrating 2:3:5:6-tetrachlorophenol, was also a by-product of the preparation of (IV) and 2:3:5:6-tetrachloro-4-nitroanisole from (III) by amination and the action of sodium methoxide, respectively. Replacement of chlorine or demethylation occurred when 2:3:5:6-tetrachlorobenzene-diazonium sulphate or its 4-methoxy-derivative was decomposed in aqueous sodium acetate, giving 3:4:6-tri-chlorobenzene-2-diazo-l-oxide or 2:3:5:6-tetrachlorobenzene-4-diazo-l- oxide, respectively.