Tetraazidomethane

Tetraazidomethane
IUPAC name Tetraazidomethane
Identifiers
CAS number	869384-16-7
PubChem	16059578
ChemSpider	17219283 Y
Jmol-3D images	{{#if:[N-]=[N+]=N\C(\N=[N+]=[N-])(\N=[N+]=[N-])\N=[N+]=[N-]|Image 1
SMILES [N-]=[N+]=N\C(\N=[N+]=[N-])(\N=[N+]=[N-])\N=[N+]=[N-]
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
Properties
Molecular formula	CN12
Molar mass	180.09 g/mol
Boiling point	~165 °C (estimate)
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

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