Tetraazidomethane

Tetraazidomethane

Names
IUPAC name Tetraazidomethane
Identifiers
CAS Number	869384-16-7
3D model (JSmol)	Interactive image
ChemSpider	17219283
PubChem CID	16059578
CompTox Dashboard (EPA)	DTXSID20581604
InChI InChI=1S/CN12/c2-10-6-1(7-11-3,8-12-4)9-13-5 Key: PGNZIEKVQCKOBT-UHFFFAOYSA-N 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	CN12
Molar mass	180.09 g/mol
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).

Tetraazidomethane is a colorless, highly explosive liquid. Its chemical structure consists of a carbon atom substituted with four azide functional groups.

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 surprising reactions including hydrolysis, cycloaddition reactions with alkenes and alkynes, and reaction with phosphines to form phosphazenes.^[1]

References