Identification of a toxic impurity in commercial diphenylamine

Abstract
The impurity in commercial diphenylamine which induces poly‐cystic kidney disease in rats has been identified as N,N,N'‐tri‐phenyl‐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‐phenylene‐diamine. Laboratory studies with highly purified diphenylamine indicated that N,N,N'‐triphenyl‐p‐phenylenediamine can be formed by heating diphenylamine.

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