1-Diazidocarbamoyl-5-azidotetrazole

1-Diazidocarbamoyl-5-azidotetrazole, often jokingly referred to as azidoazide azide, is a heterocyclic inorganic compound with the formula C2N14. It is a highly reactive and extremely sensitive explosive.

Synthesis
1-Diazidocarbamoyl-5-azidotetrazole was produced by diazotizing triaminoguanidinium chloride with sodium nitrite in ultra-purified water. Another synthesis uses a metathesis reaction between isocyanogen tetrabromide in acetone and aqueous sodium azide. This first forms isocyanogen tetraazide, the "open" isomer of C2N14, which at room temperature quickly undergoes an irreversible cyclization reaction to form a tetrazole ring.
 * Isocyanogen tetraazide closure.png

Properties
The C2N14 molecule is a monocyclic tetrazole with three azide groups. This ring form is in equilibrium with isocyanogen tetraazide, an isomeric acyclic structure that has long been known to cyclize quickly to the tetrazole.

It is one of a family of high energy nitrogen compounds in which the nitrogen atoms do not have strong triple bonds. This instability makes many such compounds liable to explosive decomposition, releasing nitrogen gas.

This tetrazole explosive has a decomposition temperature of 124 °C. It is very sensitive, with an impact sensitivity lower than 0.25 joules. It is, however, less sensitive than nitrogen triiodide. Decomposition can be initiated by only using contact or using a laser beam. For these reasons, it is often erroneously claimed to be the world's most sensitive compound.