Tetraazidomethane

"CN12" redirects here. For cranial nerve 12, see hypoglossal nerve.
Tetraazidomethane
Tetraazidomethane
Tetraazidomethane
Tetraazidomethane
Tetraazidomethane
Names
Preferred IUPAC name
Tetraazidomethane
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/CN12/c2-10-6-1(7-11-3,8-12-4)9-13-5 checkY
    Key: PGNZIEKVQCKOBT-UHFFFAOYSA-N checkY
  • InChI=1/CN12/c2-10-6-1(7-11-3,8-12-4)9-13-5
    Key: PGNZIEKVQCKOBT-UHFFFAOYAX
  • [N-]=[N+]=N\C(\N=[N+]=[N-])(\N=[N+]=[N-])\N=[N+]=[N-]
Properties
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 checkY☒N ?)

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.

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]

References

  1. ^ a b "The Exciting Chemistry of Tetraazidomethane", Klaus Banert, Young-Hyuk Joo, Tobias Ruffer, Bernhard Walfort, and Heinrich Lang, Angew. Chem. Int. Ed. 2007, 46, 1168–1171. doi:10.1002/anie.200603960
  2. ^ "Tetraazidomethane: Chemistry with a Bang", Chemical & Engineering News, Dec. 18, 2006, 46.