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Further Studies on the Carcinogenicity of Dyes Related to 4-Dimethylaminoazobenzene. The Requirement for an Unsubstituted 2-Position^*

( McArdle Memorial Laboratory, Medical School, University of Wisconsin, Madison, Wis., and the Division of Fluorine Chemistry, Illinois State Geological Survey, Urbana, Ill.)

A study of the carcinogenicities of various fluoro and other derivatives of 4-dimethylaminoazobenzene (DAB) in the rat liver has indicated that an unsubstituted 2-position in this dye is necessary for carcinogenic activity.

The following compounds had moderate to strong carcinogenic activity: 3-fluoro-DAB, 3',4'-difluoro-DAB, 2,5,2',5'-tetrafluoro-DAB, 2'-methoxy-DAB, 3'-methoxy-DAB, 4'-methoxy-DAB, and 4'-ethyl-DAB.

The following compounds had only weak carcinogenic activity: 3-methyl-DAB, 2-methyl-4-monomethylaminoazobenzene, and 3',4'-dimethyl-DAB.

The following compounds had no detectable carcinogenic activity: 2,6-difluoro-DAB, 2,6,3',5'-tetrafluoro-DAB, 2,6,2',4',6'-pentafluoro-DAB, 3-hydroxy-DAB, DAB methochloride, 2-acetylamino-5-dimethylaminodiphenylamine, 2-nitro-5-dimethylaminodiphenylamine, 3,4-dinitrodimethylaniline, 4'-amino-4-dimethylaminodiphenylamine, 4'-imino-4-dimethylaminodiphenylimine sulfate, benzo[c]cinnoline, 2-dimethylaminobenzo[c]cinnoline, the dihydrochloride and N-acetyl derivative of N,N-dimethyl-p-phenylene diamine, aniline hydrochloride, N-acetyl m-toluidine, sodium p-dimethylaminobenzene diazonium sulfonate, and 4,4'-bis(dimethylamino)azobenzene.

The syntheses of several new derivatives of DAB are described. These are 3-fluoro-, 2,6-difluoro-,3',4'-difluoro-, 2,5,2',5'-tetrafluoro-, 2,6,3',-5'-tetrafluoro-, 2,6,2',4',6'-pentafluoro-, 3'-methoxy-, 4'-ethyl-, 3',4'-dimethyl-, and 3-hydroxy-DAB.

^* This investigation was supported in part by grant C355 of the National Cancer Institute, U.S. Public Health Service, Institutional Grant 71 from the American Cancer Society, and the Alexander and Margaret Stewart Trust Fund.

Received 12/31/56.