Nitro p-toluidine

Tetronitro-4-methyldiphenylamine or N-(2, 4, 61 -Trinitrophenyl)-2-nitro-p-toluidine, (OaN)sC6Ha.NH.C,H,(NOa). CHS golden-bm plates, mp 217-19°. Can be prepd by heating a mixt of picryl chloride and 3-nitro-p-toluidine to 160° (Ref 2). Its expl props, were not examined... 

Nitroso-R-salt, n82 Nitroterephthalic acid, n31 2-Nitro-p-toluidine, m317 4-Nitro-e>-toluidine, m315... 

The same authors also introduced a r scale of solvent dipolarity/polarizability [84a]. This n scale is so named because it is derived from solvent effects on the n n electronic transitions of a selection of seven positively solvatochromic nitroaromatics of the type D-C6H4-A, where D and A stand for electron-donor e.g. NMe2) and electron-acceptor e.g. NO2) groups, respectively 4-nitroanisole, A,A-diethyl-3-nitroaniline, 4-methoxy-/ -nitrostyrene, 1-ethyl-4-nitrobenzene, A-methyl-2-nitro-p-toluidine, N,N-diethyl-4-nitroaniline, and 4-(dimethylamino)benzophenone. Given a solvatochromic indicator compound, the n value for a solvent S was defined according to Eq. (7-32) ... 

Aromatic amines are often acetylated before nitration. Examples include the nitration of p-acetotoluide and 2-acety]aminonaphthalene, the products being 3-nitro-p-acetotoluide (90%) and l-nitro-2-acetylamino-naphthalene (49%), respectively. The p-tolylsulfonyl derivative is readily formed and hydrolyzed after nitration. On the other hand, if unacetylated and in the presence of a large excess of sulfuric acid, p-toluidine gives mainly 2-nitro-p-toluidine (71%), the arylammon um ion being meta-directing. 

N, JV-Dimethyl-2-nitro-p -toluidine N, JV-Dimethyl-2-nitro-p -anisidine A,jV-E>iethyl-3-nitroaniline A -Dimethyl-d-nitrosoaniline A -Dimethyl-d-nitroaniline A,A-I)iethyl-4-nitroaniline N, A-Diethyl-3-methyl-4-nitro aniline N,N, 3,5-Tetramethyl-4-nitroaniline 4-N,N -Dimethylaminobenzophenone Ethyl 4-Ar,iV-dimethylaminobenzoate 4-(Ar,Ar-Dimethylamino)-/S-nitrostyrene 4-(jV,jV-Dimethylamino)benzaldehyde... 

Conversion of Phenols to Amines. Aniline and some diphenylamine are formed when phenol and NHs solution are heated under pressure in the presence of FeCh, Al(OH)s, or Fe(OH)j. When NH and phenol or ortho-or para-cresols are reacted in the vapor phase over an AljO catalyst, yields of up to 88 per cent of the corresponding amines are obtained. However, these amines are customarily obtained by reducing the parent nitro compound, except in cases where it is difficult to obtain the required nitro isomer. For example, it is considered that the amination of symr xylenol is the best method of preparing sym-xylidine (l-amino-3,5-di-methylbenzene). When sym-xylenol is heated under pressure to 320 C with ammonium chloride, about equal amounts of sj/m-xylidine and sym-dixylylamine (5-imino-bis-l,3-dimethylbenzene) are formed. The ortho-and para-nitrophenols and nitrocresols can be aminat more readily. 2-Nitro-p-cresol [OH(l), N02(2), CHj(4)] and o-nitrophenol have been aminated in aqueous ammonia containing ammonium salts of weak acids to inhibit decomposition. Phosphoric, boric, carbonic, and formic acids were used. In one case it is claimed that 55-65 per cent yields of 2-nitro-p-toluidine (MNPT of commerce) were obtained when 2-nitro-p-cresol, 28 per cent aqueous NHj, and monoammonium phosphate, 1 11.5 0.2 molar ratio, were heated under pressure for 10 hr at 140-150°C and then 5 hr at about 160 C. Earlier workers, employing somewhat similar conditions, claimed excellent yields of MNPT when 1 mole of ammonium formate was used per mole of 2-nitro-p-cresol. ... 

The IT Scale. Proposed in 1977 by the present authors (33h) this scale is based on the solvent-induced shifts of the frequency maxima of the x - ir transitions of seven indicators 4-nitroanisole (VII), N,N-diethyl-3-nitro-aniline (VIII), 4-methoxy-/S-nitrostyrene (IX), l-ethyl-4-nitrobenzene (X), N-methyI-2-nitro-p-toluidine (XI), N,N-diethyl-4-nitroaniline (XII) and 4-di-methylaminobenzophenone (XIII). 

The 13 scale has been amended and expanded through three subsequent studies. In the first of these (76), the solvatochromic comparison method was applied to three HBD indicators, 2-nitroaniline (6), 2-nitro-p-toluidine (7), and 2-nitro-p-anisidine (8), and their corresponding N,N-dimethyl derivatives (6a, 7a, 8a). 

Methyl-2-nitrobenzeneamine 3-Nitro-4-aminotoluene 2-Nitro-4-methylaniline 2-Nitro-p-toluidine p-Toluidine, 2-nitro-... 

Nitro-p-toluidine. See 3-Nitro-p-toluidine 4-Methyl-2-nitroaniline... 

Toluidine reds n. Pigment red 3 (12120). Series of red dyestuffs made by diazotizing 2-nitro-p-toluidine and coupling this with P naphthol under alkaline conditions. By altering the conditions of preparation, reds of different shade, brilliance, strength, etc. are obtained. 

Figure 1.7 Thermal UV profile of (a) 1 1 mixture of organic pigment yellow (2-nitro-p-toluidine coupled with acetoacetanilide and inorganic pigment PY 34 (lead chromate), (b) PB 15.4 copper phthalocyanine (beta form) PG 7 polychlorinated copper phthalocyanine (14-16 chlorine atoms)...

Toluidine red, Cl Pigment Red 3 Colour Index, 1971), is hy volmne one of the 20 largest organic pigments in the world. A fj-naphthol azo pigment q.v.), it is diazotised 2-nitro-p-toluidine coupled with alkaline P-naphthol, and was first synthesised in 1904 by Meister Lucius and Bruning (Herbst and Hunger, 1997 de Keijzer, 1999). It is used extensively in conjunction with molybdate red q.v.). 

Monoazo yellow (2-nitro-p-toluidine coupled with a acetoacetanilide) or (hansa) yellow. They have high tinting strength and a good chemical resistance. 

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