Triazenes safety

Azo couplings of diazonium salts with primary or secondary amines give triazenes which are normally hard to get in pure form. It is, however, quite easy to get triazenes with aliphatic or aromatic amines if solid-state techniques are applied that give rise to pure products in quantitative yield [98-100]. The di-methyltriazenes 309 have been quantitatively obtained by very cautious addition of gaseous dimethylamine (exothermic ) [98] (Scheme 47). Extreme care has to be taken for safety reasons ... 

Scheme 48). From there, neutralization leads to the free triazenes 312,314, and 315 with insignificant losses (<1%) [99-100]. The compounds 315 are almost isoenergetic with their tautomers as formed by 1,3-H shift to the other N atom according to DTF calculations at the B3LYP/6-31G level [100]. The precautions during grinding should be followed for safety reasons ... 

SYNS 3.3-DIMETHYHl-(m-TOLYL)TRIAZENE l-(m-METHYLPHENYL)-3,3-DIMETHYLTRIAZENE l-(3-METHYLPHENYL)-3,3-DIMETHYLTRIAZENE SAFETY PROFILE Poison by ingestion and intraperitoneal routes. Moderately toxic by subcutaneous route. Questionable carcinogen with experimental carcinogenic data. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx. 

Safety Note. Because acyclic triazenes are potent biological alkylating agents, it is only prudent to assume that triazolines are also potentially toxic and carcinogenic. Efficient hoods and protective clothing should be used in working with these substances. Alkyl azides are treacherously explosive and should be treated with extreme caution. Wherever possible these compounds should only be handled as solutions. 

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See also in sourсe #XX -- [ , , , , ]

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