Tetraazidomethane

Chembox new
Name = Tetraazidomethane
ImageFileL1 = tetraazidomethane.png ImageSizeL1 = 120px
ImageNameL1 = Tetraazidomethane
ImageFileR1 = tetraazidomethane 3D.png ImageSizeR1 = 120px
ImageNameR1 = Tetraazidomethane
IUPACName = Tetraazidomethane
Section1 = Chembox Identifiers
CASNo = 869384-16-7
SMILES = [N-] = [N+] =NC(N= [N+] = [N-] )(N= [N+] = [N-] )N= [N+] = [N-]
Section2 = Chembox Properties
Formula = CN₁₂
MolarMass = 180.09 g/mol
Density =
BoilingPt = ~165 °C ("estimate")

Tetraazidomethane is a colorless, highly explosive liquid. Its chemical structure consists of a carbon atom substituted with four azide functional groups. It was first prepared by Klaus Banert in 2006 by reaction of trichloroacetonitrile with sodium azide."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]

Uses

As with other polyazides, tetraazidomethane has interest as a high-energy-density material with potential uses in explosives, propellants, or fireworks. ["Tetraazidomethane: Chemistry with a Bang", "Chemical & Engineering News", Dec. 18, 2006, 46.]

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.

References