420. o-Aminoazotoluene

Nomenclature

CAS number: 97-56-3
2-Methyl-4-[2-(2-methylphenyl)diazenyl]benzenamine; 2-methyl-4-[(2-methylphenyl)azo]benzenamine; C.I. Solvent Yellow 3; 4-(o-tolylazo)-o-toluidine; 4′-amino-2,3′-dimethylazobenzene; 5-(o-tolylazo)-2-aminotoluene; toluazotoluidine; C.I. 11160.
C14H15N3; mol wt 225.29.
C 74.64%, H 6.71%, N 18.65%.

Description and references

Prepd from o-toluidine, NaNO2, and HCl: Shulman, US 2538431 (1951 to Pfister Chem. Works); Colour Index vol. 4 (3rd ed., 1971) p 4017. Crystal and molecular structure: S. Kurosaki et al., Acta Crystallogr. 32B, 3160 (1976) DOI. Carcinogenic activity: Maini, Stich, J. Natl. Cancer Inst. 26, 1413 (1961) PubMed. See also: H. J. Conn's Biological Stains, R. D. Lillie, Ed. (Williams & Wilkins, Baltimore, 9th ed., 1977) p 87.

Chemical structure

Properties

Golden crystals, mp 101-102°. Practically insoluble in water. Sol in alc, ether, chloroform, acetone, ethyl acetate, benzene, ligroin, linseed oil, oleic acid, stearic acid. Very sol in cellosolve. Absorption max (50% alcoholic 1N HCl): 326, 490 nm (ε 19000, 2500), Sawicki, J. Org. Chem. 21, 605 (1956) DOI.

Caution

This substance is reasonably anticipated to be a human carcinogen: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-12.

Use

Coloring oils, fats and waxes; manuf of pigments. Chemical intermediate for the production of dyes.