Tetraazidomethane

"CN12" redirects here. For cranial nerve 12, see hypoglossal nerve.

Tetraazidomethane, C(N₃)₄, is a colorless, highly explosive liquid. Its chemical structure consists of a carbon atom covalently bonded to four azide functional groups.

Tetraazidomethane

Tetraazidomethane Tetraazidomethane
Names
Preferred IUPAC name Tetraazidomethane
Identifiers
CAS Number	869384-16-7 N
3D model (JSmol)	Interactive image
ChemSpider	17219283 Y
PubChem CID	16059578
CompTox Dashboard (EPA)	DTXSID20581604
InChI InChI=1S/CN12/c2-10-6-1(7-11-3,8-12-4)9-13-5 Y Key: PGNZIEKVQCKOBT-UHFFFAOYSA-N Y InChI=1/CN12/c2-10-6-1(7-11-3,8-12-4)9-13-5 Key: PGNZIEKVQCKOBT-UHFFFAOYAX
SMILES [N-]=[N+]=N\C(\N=[N+]=[N-])(\N=[N+]=[N-])\N=[N+]=[N-]
Properties
Chemical formula	C(N3)4
Molar mass	180.095 g·mol−1
Appearance	Colorless liquid
Boiling point	~165 °C (estimate)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Tetraazidomethane with central carbon in black, and 4 tetrahedral branches of 3 nitrogens, yellow as double bonds.

Synthesis

It was first prepared by Klaus Banert in 2006 by reaction of trichloroacetonitrile with sodium azide.^[1]

Uses

As with other polyazides, tetraazidomethane has interest as a high-energy-density material with potential uses in explosives, propellants, or fireworks.^[2] Silicon tetraazide is also a known compound.

Reactions

Banert has reported that tetraazidomethane participates in a number of reactions including hydrolysis, cycloaddition reactions with alkenes and alkynes, and reaction with phosphines to form phosphazenes.^[1]