A study on 2-Amino-4-nitrophenol

14/02/2014 10:46

2-Amino-4-nitrophenol which is also known as 4-Nitro-2-Aminophenol and 4-NAP, it is a kind of orange prisms or yellow powders with Molecular Formula:C6H6N2O3 and Molecular Weight: 154.12. It is slightly soluble in water, stable under normal temperatures and pressures. The CAS Registry Number of 2-Amino-4-nitrophenol is 99-57-0 .

2-Amino-4-nitrophenol is produced by the reaction of 2,4-dinitrophenol with sodium sulfide. It was first sythesized by Agfa in 1898. At present, approximately 150 kg of 2-amino-4-nitrophenol are used in hair colouring products in the USA annually, according to industry estimates.

2-Amino-4-nitrophenol(CAS NO:99-57-0) is used as an intermediate in the manufacture of CI MordantBrown 33 and CI Mordant Brown 1, which are used for dyeing leather, nylon, silk, wool andfur. It is also used in some countries as a dye in semi-permanent hair colour products to produce gold-blond shades.

These products are generally shampooed into the hair, lathered and then allowed to remain in contact with the hair and scalp for 30-45 min. For this application, 2-amino-4-nitrophenol is mixed at levels up to 0.5 % with a blend of several other dyes in a shampoo base to produce the final colour or tint. It has also been used in permanent hair colouring products.

4-Amino-2-nitrophenol has been used as an oxidation base in formulations of hair dyes. Technical grade 4-amino-2-nitrophenol induced tumors of the urinary bladder in male rats, and there is some evidence for a similar effect among female rats. Tumors of the urinary bladder are extremely rare among untreated rats.

Preparations of 4- amino-2-nitrophenol have also demonstrated genotoxic potential in a number of short-term tests in bacterial and mammalian cells, in vitro and in vivo. There is some evidence that a purified preparation of 4-amino-2-nitrophenol loses its genotoxic potential, although this has only been investigated in a single study. In support of the concern for the carcinogenicity of 4-amino-2-nitrophenol itself, the purity of the test substance administered in the studies showing the development of bladder tumors was of relatively high purity.

Furthermore, aromatic amines with structural homology to 4-amino-2-nitrophenol have shown evidence of carcinogenicity, some with the urinary bladder as the site of tumor development.

There is evidence for the carcinogenicity of 4-amino-2-nitrophenol, with development of transitional cell carcinomas of the urinary bladder, a rare tumor, observed in male mice. The weight of evidence is supported by observations of a small number of the same rare tumor type in female mice, by mutagenicity in several short-term tests, and by chemical structural analogies with known carcinogens, including several bladder carcinogens.

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