Model studies for azo dye carcinogenesis

Abstract

The isomeric 2′-,3′-, and 4′-hydroxymethyl-4-dimethylaminoazobenzenes have been prepared. The corresponding chloromethyl compounds have been isolated from reactions of the 3′- and 4′-isomers with thionyl chloride, but rapid formation of the indazole ring system precluded the isolation of a chloromethyl derivative from the 2′-isomer. The 3′- and 4′-chloromethyl and iodomethyl derivatives reacted with DNA in vitro.