Nitro-p-Cresol

Yellow crystals, slightly soluble in water, soluble in alcohol and ether Combustible 

Toxic by ingestion, inhalation and skin absorption Irritant 

Uses mostly as an intermediate in the dyestuff industry Manufacturers There are a number of manufactures including a few Chinese companies, Sumitomo Chemical Co., Japan, Bayer AG, Atul. Most of them consume the product captively. 

3-Amino-4-methoxy toulene White crystals and soluble in 

Till a few years ago, p-cresidine used to be a very important dye intermediate. However, this was one of the products with an amino (-NH2) group and was in the banned list of 22 azo compounds, by Germany. Though this was not an azo dye intermediate, however, being in the banned category, demand was restricted in Germany and elsewhere. 

---

Dinitro-p-cresol, yel-brn ndls (from ale), mp 112-13° prepd by nitrating 2-nitro-p-cresol in AcOH at 18-25°with HN03, together with other products (Ref 3, p [ 391 ] )... 

Kurebayashi H, Nambaru S, Fukuoka M, Yamaha T, and Tanaka A (2002) Metabolism and excretion of 2-nitro-p-cresol in rats. Archives of Toxicology 76 676-681. 

Derivation 2-Nitro-p-cresol, obtained by the action of nitrous and excess nitric acids uponp-toluidine, is methylated and reduced. 

Beilstein Handbook Reference) 4-Hydroxy-3-nitrotoluene AI3-15389 BRN 1868022 EINECS 204-3106 NSC 5387 2-Nitro-4-cresol 2-Nitro-p-cresol 2-Nitto-4-methylphenol 0-Nitro-p-cresol pCresol, 2-nitro-. Yellow needles mp = 36.5° bp = 125° d = 1.2399 very soluble in Me2CO, CeHe, EtzO, EtOH. 

Amino-p-cresol (OH = l) 68 A solution of 2-nitro-p-cresol (10 g) in water (200 ml) and concentrated ammonia solution (50 ml) is added slowly to one of sodium dithionite (75 g) in water (300 ml). A white, crystalline but flocculent precipitate appears in 5 min, the red color of the solution changing to pale yellow. The whole mixture (unfiltered) is extracted with ether. The extract is dried, treated with charcoal, and evaporated, yielding yellowish-brown crystals (6.8 g, 81%), m.p. 134-135°. 

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. ... 

---