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 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.

Hazards

Nearly any stimulus, such as heat, radiation, or physical shock, will cause 1-diazidocarbamoyl-5-azidotetrazole to detonate. It may also detonate unpredictably and for no apparent reason. This is part of the high energy nitrogen compound family as the nitrogen atoms do not have strong triple bonds and so are stuck in a high energy state until detonation and then change into a less energetic state. When an attempt was made to chart its infrared spectrum using Raman spectroscopy, it exploded.
However, at least two chemistry hobbyists have claimed to have produced the compound, using the isocyanogen tetrabromide and sodium azide method, and documented their results online. Preliminary qualitative observations suggested that although still highly sensitive, the compound is much less so than traditionally described, requiring moderate force to trigger a detonation.