1-Diazidocarbamoyl-5-azidotetrazole, often jokingly referred to asazidoazide azide,^[5] is aheterocyclicinorganic compound with the formula C₂N₁₄.^[6] It is a highly reactive andextremely sensitiveexplosive.

1-Diazidocarbamoyl-5-azidotetrazole

Names
Preferred IUPAC name N-(5-Azido-1H-tetrazol-1-yl)carbonimidoyl diazide
Other names 1-Diazidocarbamoyl-5-azidotetrazole 5-Azido-1-diazidocarbamoyltetrazole N-(5-Azido-1H-tetrazol-1-yl)carbonimidic diazide
Identifiers
CAS Number	1306278-47-6[1] N
3D model (JSmol)	Interactive image
Abbreviations	AA
ChemSpider	30649737
PubChemCID	101796054
CompTox Dashboard(EPA)	DTXSID901336271
InChI InChI=1S/C2N14/c3-11-6-1(7-12-4)10-16-2(8-13-5)9-14-15-16 Key: ROKXTJDNIZBVDB-UHFFFAOYSA-N
SMILES N(=[N+]=[N-])C1=NN=NN1N=C(N=[N+]=[N-])N=[N+]=[N-]
Properties
Chemical formula	C2N14
Molar mass	220.120 g·mol−1
Density	1.723 g·cm−3[2]
Melting point	78 °C (172 °F; 351 K)
Boiling point	Violent explosion at 110 °C
Solubility	Soluble indiethyl ether,acetone, hydrocarbons, chlorinated hydrocarbons[3]
Structure[4]
Crystal structure	orthorhombic
Space group	Pbcn
Lattice constant	a = 18.1289,b = 8.2128,c = 11.4021
Lattice volume (V)	1697.6
Formula units (Z)	8
Thermochemistry
Std enthalpy of formation(ΔfH⦵298)	357 kcal·mol−1[5] (1495 kJ·mol−1)[2]
Explosive data
Shock sensitivity	<0.25 J
Friction sensitivity	<1 N
Detonation velocity	8960 m·s−1
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	will unpredictably and violently detonate – part of the nitrogen highly energetic compounds family.
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). Infobox references

1-Diazidocarbamoyl-5-azidotetrazole was produced bydiazotizing triaminoguanidinium chloride withsodium nitrite in ultra-purifiedwater.^[6] Another synthesis uses ametathesis reaction betweenisocyanogen tetrabromide inacetone and aqueoussodium azide.^[3] This first forms isocyanogen tetraazide, the "open" isomer of C₂N₁₄, which at room temperature quickly undergoes an irreversible cyclization reaction to form atetrazole ring.^[7]

The C₂N₁₄ molecule is a monocyclic tetrazole with threeazide groups. This ring form is inequilibrium with isocyanogen tetraazide, anisomeric acyclic structure that has long been known to cyclize quickly to the tetrazole.^[7]

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, releasingnitrogen 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 thannitrogen triiodide. Decomposition can be initiated by only using contact or using a laser beam.^[8] For these reasons, it is often erroneously claimed to be the world's most sensitive compound.^[9][5]

•   The dictionary definition ofazidoazide azide at Wiktionary

• Synthesis video onYouTube
• Discussion between discoverer and hobby chemists about the synthesis video onYouTube