Identification of a toxic impurity in commercial diphenylamine.
The impurity in commercial diphenylamine which induces polycystic kidney disease in rats has been identified as N,N,N'-triphenyl-p-phenylenediamine. The structure of the compound was confirmed by mass and proton magnetic resonance spectrometry and by comparison with a synthetic standard prepared by the Ullman coupling of iodobenzene and p-phenylenediamine or N,N-diphenyl-p-phenylenediamine. Laboratory studies with highly purified diphenylamine indicated that N,N,N'-triphenyl-p-phenylenediamine can be formed by heating diphenylamine.
D000814:Aniline Compounds / Q000032:analysis*; D000818:Animals; D004159:Diphenylamine / Q000032:analysis*; D004340:Drug Contamination; D010655:Phenylenediamines / Q000302:isolation & purification* / Q000633:toxicity; D051381:Rats
D000814:Aniline Compounds; D010655:Phenylenediamines; C031502:N,N,N'-triphenyl-4-phenylenediamine; D004159:Diphenylamine