1,1'-dinitro-3,3'-azo-1,2,4-triazole

I searched without results here for both this chemical's name and that of its precursor, the herbicide aminotriazole (3-amino-1,2,4-triazole), so I assume that this has not been discussed here before.

Amitrol is the name that this herbicide is sold under by Bayer Crop Science.

Patent US4623409 teaches the preparation of this explosive in 2 steps from the herbicide:

a. KMnO4 oxidation to form the 3,3'-azo-1,2,4-triazole intermediate.

b. Nitration to get the explosive.

This work was done by the U.S. DOE. It is claimed to be both a propellant & an explosive. Patent US6156136 (to SRI Intl) discloses a different synthetic method & other information.

Their are a number of additional references via Google that are too numerous to list here. One interesting one covers crystalline polymorphs, an important area when considering the optimization of both the process & the product performance. See Acta Cryst. (1988). C44, 1673-1674. Apparently the polymorphs have distinct colors ('yellow polymorph'), a useful qualitative test to identify which one you might have. Without having seen the references on this, this might indicate cis/trans isomerism at the azo group.



[Edited on 24-7-2008 by Ritter]

1,1'-dinitro-3,3'-azo-1,2,4-triazole (N-DNAT)