P-Chloro-o-nitroaniline

Fig. 1.11 Dissociation ranges of colour indicators for determination of the acidity function H0 in H2S04-H20 mixtures (1) p-nitroaniline, (2) o-nitroaniline, (3) p-chloro-o-nitroaniline, (4) p-nitrodiphenylamine, (5) 2,4-dichloro-6-nitroaniline, (6) p-nitroazobenzene, (7) 2,6-dinitro-4-methylaniline, (8) benzalacetophenone, (9) 6-bromo-2,4-dinitroaniline, (10) anthraquinone, (11) 2,4,6-trinitroaniline. (According to L. P. Hammett and A. J. Deyrup)...

Synonyms Aniline, 4-chloro-2-nitro- Azoene fast red 3GL base Azoene fast red 3GL salt Azofix red 3GL salt Azoic diazo component 9 Benzenamine, 4-chloro-2-nitro- p-Chloro-o-nitroaniline 4-Chloro-2-nitrobenzenamine 4-Chloro-2-nitrobenzeneamine Cl 37040 Cl azoic diazo component 9 Fast red base 3GL special Fast red 3GL base Fast red 3GL salt Naphthanil red 3G base 2-Nitro-4-chloroaniline PCON PCONA Red base 3GL Red 3G base Empirical C6H5CIN2O2 Formula C6H3CINO2NH2... 

The photometric determination of mixtures of aniline, p-nitroaniline and o-nitroaniline was described. Distribution coefficients and separation efficiency of these compounds by LLE in various solvents were compared517. Substituted nitroanilines such as 2-chloro-4-nitroaniline and 2,4-dinitroaniline are intermediates in the manufacture of the dye D C Red No. 36 and were identified as impurities by RP-LC518. A spectrophotometric method was developed for the determination of aniline and m-nitroaniline in a mixture of aniline and nitroaniline isomers by derivatization with 5,7-dichloro-4,6-dinitrobenzofuroxan (244). The relative error of the determination is <5%519. See also Section IV.D.3.b for similar derivatives. 

Fig. 3.61. HPLC-UV chromatogram at 230 nm for the analysis of the aromatic amines listed. (1) 1,4-Diaminobenzene (2) 2-chloro-l,4-diaminobenzene (3) 2,4-diaminotoluene (4) benzidine (5) 4,4 -oxidianiline (6) aniline and 4-nitroaniline (7) o-toluidine (8) 4,4 -methylenedianiline (9) 3,3 -dimethoxibenzidine (10) 3,3 -dimethylbenzidine (11) 4-chloroaniline and 2-amino-4-nitrotoluene (12) 4,4 -thiodianiline (13) p-cresidine (14) 2,4-dimethylaniline (15) 2-naphty-lamine (16) 4-chloro-o-toluidine (17) 4,4 -methylene-di-o-toluidine (18) 2,4,5-trimethylaniline (19) 4-aminobiphenyl (20) 3,3 -dichlorobenzidine (21) 4,4 -methylenbis (2-chloroaniline) and (22) o-aminoazotoluene. Reprinted with permission from M. C. Garrigos et al. [130].

Remarks. Nitro-p-dichlorobenzene can be reduced to p-dicbloroaniline in tbe usual way with iron and a small amount of acid. Tbe chlorine ortbo to tbe nitro group is labile and can be replaced by various substituents, less easily, however, than the chlorine in 2,4-dinitrochlorobenzene, but more easity than that in o-nitrochloro-benzene. The replacement of the chlorine by hydrojyl by the action of aqueous sodium hydroxide is described in the following preparation. Reaction wiUi sodium methylate yields 4-chloro-2-nitroanisole, which is reduced to 4-chloro-2-am sidine (chloramsidine P, or fast red R base). With ammonia under pressure, 4-chloro-2-nitroaniline (fast red 3CL base) is formed. These bases are important starting materials for the preparation of azo dyes, especial pigment and lake coIots, as well as ice colors. 

FAST RED BASE or FAST RED GG BASE or FAST RED IG BASE or FAST RED 2G BASE (100-01-6) p-nitroaniline. FAST RED TR BASE (95-79-4) see 5-chloro-o-toluidine. 

Continuous Preparation of Nitroanilines. The I.G. Farbenindustrie developed a continuous process for the ammonolysis of o-chloronitroben-zene, p-chloronitrobenzene, 2,5-dichloronitrobenzene, and 3,4-dichloronitro-benzene to o-nitro-, p-nitro-, 4-chloro-2-nitro-, and 2-chloro-4-nitroanilines, respectively. The facilities are shown diagrammatically in simplified form in Fig. 8-23. 

Niter. See Potassium nitrate Nitramin. See 2-Amino-5-nitrothiazole Nitramyl. See Isoamyl nitrite 4-Nitraniline. See p-Nitroaniline m-Nitraniline. See m-Nitroaniline o-Nitraniline. See o-Nitroaniline p-Nitraniline. See p-Nitroaniline Nitrapyrin. See 2-Chloro-6-(trichloromethyl) pyridine... 

Anthracene Anthranilic acid Anthraquinone Antimony pentachloride Benzaldehyde Benzidine dihydrochloride 2,2 -Benzidinedisulfonic acid Benzoguanamine Benzotrifluoride Benzoyl chloride N-Benzylamine N-Benzyl-N-ethyl-m-toluidine Bisphenol A Bromine 4-Bromochloro benzene Butyl acetoacetate n-Butylamine t-Butylamine Ceteareth-15 o-Chloroaniline p-Chloroaniline m-Chlorobenzoic acid o-Chlorobenzoic acid p-Chlorobenzoic acid m-Chlorobenzotrifluoride o-Chlorobenzotrifluoride p-Chlorobenzotrifluoride Chloroform 4-Chloro-2-nitroaniline 2-Chloronitrobenzene... 

Figure 2. The ionization ratio measured for a series of indicators plotted against the weight percent of sulfuric acid in the H2O—H2SO4 system. (Reprinted from Ref 12 with permission of the American Chemical Society.) 1 p-Nitroaniline, 2 o-nitroaniline, 3 4-chloro-2-nitroaniline, 4 p-nitrodiphenylamine, 5 2,4-dichloro-6-nitroaniline, 6 p-nitroazobenzene, 7 2,6-dinitro-4-metiiylaniline, 8 2,4-dinitroaniline, 9 A, A -dimethyl-2,4,6-trinitroaniline, 10 benzalacetophenone, 11 8-benzoylnaphthalene, 12 p-benzoyldiphenyl, 13 6-bromo-2,4-dinitroaniline, 14 anthraquinone, 15 2,4,6-trinitroaniline. (Reprinted fi-om Ref 12 with permission fi-om the American Chemical Society.)...

The products produced by interaction of diazonium salts and iodides are unstable and liable to be explosive in the solid state. They are usually the triiodides, but monoiodides have been isolated under specific conditions from diazotised aniline and o-toluidine. Products prepared from diazotised o-, m- or p-nitroanilines, m-chloro-, -methoxy-, or -methyl-aniline are too unstable to isolate, decomposing below 0°C. 

The effect of nuclear chloro and nitro groups, alone, on the yields in the Bechamp reaction has not been studied. However, the reaction proceeds in the expected manner with o- 68 64 and p-nitroaniline 66 >66 and o-59 and p-chloroaniline,67 but fails completely with o-nitrophenol.68... 

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