Diamino-chlorobenzene

SYNS p-CHLORO-o-PHENYLENEDIAMINE 4-CHLORO-o-PHENYLENEDIAMINE 4-CHLORO-l, 2-PHENYLENEDIAMINE 4-Ci-o-PD 1.2-DIAMINO-4-CHLOROBENZENE 3,4-DIAJ.IINOCHLOROBENZENE... 

Diamino-4-chlorobenzene 3,4-Diaminochlorobenzene 3,4-Diamino-1 -chlorobenzene. See 4-Chloro-o-phenylenediamine... 

With secondary amines46) general Scheme 25 still fits well but results are more complicated than with primary amines. Indeed, sometimes SNAr condensations appear. Moreover, it is not possible to avoid completely the formation of disubstituted products (i.e. diamino chlorobenzenes). 

This is a yellow pigment, obtained by condensing 2,5-dichloro-l,4-diamino-benzenedihydrochloride with 3-iminoisoindolinone in chlorobenzene at 140°C ... 

Watanabe T, Ishihara N, Ikeda M. 1976. Toxicity of and biological monitoring for 1,3-diamino-2,4,6-trinitrobenzene and other nitro-amino derivatives of benzene and chlorobenzene. Int Arch Occup Environ Health 37 157-168. 

Preliminary results in the validation of a novel short term test. Mutat. Res., 46, 305-310 Watanabe, T., Ishihara, N. Ikeda, M. (1976) Toxicity of and biological monitoring for 1,3-diamino-2,4,6-trinitrobenzene and other nitro-amino derivatives of benzene and chlorobenzene. Int Arch, occup. environ. Health, 37, 157-168 Yoshimi, N., Sugie, S., Iwata, H., Niwa, K., Mori, H., Hashida, C. Shimizu, H. (1988) The genotoxicity of a variety of aniline derivatives in a DNA repair test with primary cultured rat hepatocytes. Mutat. Res., 206, 183-191... 

To manufacture aniline from chlorobenzene and ammonia, cuprous oxide or diamino cuprous chloride has been used as the catalyst and the reaction is usually carried out in the liquid phase under pressure (7). There are few reports on the reaction in gas phase. Jones (8) found that CuX was active for aniline formation while ZnX led to the formation of dichlorobenzenes. The reaction of benzaldehyde with ammonia over zeolite has never been reported. 

Isoeyanato moaes. The first known member of this class, 2,5-dichloro-3,6-di-isocyanato-l,4-benzoquinone (2), was prepared by treating 2,S-diamino-3,6-dichloro-1,4-benzoquinone (I) with oxalyl chloride in butyl acetate and chlorobenzene. ... 

Similarly to 3,3 -diaminobenzidine, other aromatic o-diamines also react with selenium(rV) in HCl medium. The o-phenylenediamine method [30,31] is more sensitive than the DAB method. The following reagents have been proposed for selenium N-methyl-o--phenylenediamine (e = 1.9-10 at 346 nm) [32], 2-aminodiphenylenediamine [33], 4-nitro-1,2-diaminobenzene [34], 4,5-diamino-2,6-dimercaptopyrimidine [35], l,2-diamino-4-chlorobenzene [36], 4,5,6-triaminopyrimidine [37], 3,4-diaminobenzoic acid [38], and 2,3-diaminonaphthalene [39,40]. 

A soln. of 42 gm. of terephthalie acid dichloride in chlorobenzene dropped with stirring at 90° into a mixture of 85 gm. 2,2 -diamino-4,4 -dimethoxy-5,5 -diacetylaminodiphenyldisulfide, chlorobenzene, and aq. Na-acetate, heated 2 hrs. longer, cooled, filtered, washed, and the terephthaloyl derivative formed boiled 3 hrs. with SnCla in aq. HC1-alcohol — 60 gm. 6,6 -diamino-5,5 -dimethosy-2,2 -(p-phenylene)di-benzothiazole. (F. e. s. P. Petiteolas et al., Bl. 1949,103.)... 

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