diazo compound is diethyldiazene, EtN=NEt. Because of their instability, aliphatic azo compounds pose the risk of explosion. AIBN is produced by converting acetone cyanohydrin to the hydrazine derivative followed by oxidation: 2 (CH3)2C(CN)OH + N2H4 -> [(CH3)2C(CN)]2N2H2 + 2 H2O [(CH3)2C(CN)]2N2H2 + Cl2 -> [(CH3)2C(CN)]2N2 + 2 HCl Safety and regulation Many azo pigments are non-toxic, although some, such as dinitroaniline orange, ortho-nitroaniline orange, or pigment orange 1, 2, and 5 have been found to be mutagenic. Likewise, several case studies have linked azo pigments with basal cell carcinoma. European regulation Certain azo dyes can break down under reductive conditions to release any of a group of defined aromatic amines. Consumer goods which contain listed aromatic amines originating from azo dyes were prohibited from manufacture and sale in European Union countries in September 2003. As only a small number of dyes contained an equally small number of amines, relatively few products were affected. See also Azo coupling References Functional groups