1-Diazidocarbamoyl-5-azidotetrazole

1-Diazidocarbamoyl-5-azidotetrazole, often informally referred to as azidoazide azide, is a heterocyclic inorganic compound with the formula C2N14. It is an 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, while quickly cyclizes under standard conditions to form a tetrazole ring.
Properties.
The C2N14 molecule is a monocyclic tetrazole with three azide groups with a molecular weight of 220.16 g.mol⁻¹. It has a molecular equilibrium between a closed and an open form, isocyanogen tetraazide which has been known since 1961, the latter being quickly cyclized to the cyclic tetrazole form (C2N14) at room temperature.
Despite rumours and videos carrying exaggerated informations over this compound and despite rectifications, C2N14 is not the world's most sensitive compound ; there are other contact explosives such as nitrogen triiodide which are much more sensitive. It is however very sensitive, which impact sensitivity lower than 0,25 Joules, and of friction sensitivity less than 1 Newton.
Indeed, this tetrazole explosive has a decomposition temperature of 124°C and can be initiated on contact or using a laser beam. This is part of the high energy nitrogen compound family as the nitrogen atoms do not have strong triple bonds and are thus in a less-stable conformation until the decomposition which releases nitrogen gas.