Tetraazidomethane

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

Not to be confused with Cranial nerve 12.
Tetraazidomethane
Tetraazidomethane
Tetraazidomethane
Names
IUPAC name
Tetraazidomethane
Identifiers
3D model (JSmol)
ChemSpider
Properties
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).
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Infobox references

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
  1. "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.
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