Tetraazidomethane, , is a colorless, highly explosive liquid. Its chemical structure consists of a carbon atom covalently bonded to four azide

functional group In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the re ...

Synthesis

It was first prepared by Klaus Banert in 2006 by reaction of

trichloroacetonitrile Trichloroacetonitrile is an organic compound with the formula CCl3CN. It is a colourless liquid, although commercial samples often are brownish. It is used commercially as a precursor to the fungicide etridiazole. It is prepared by dehydration o ...

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. Tetraazidomethane synthesis 01

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. Silicon tetraazide is also a known compound.

Reactions

Banert has reported that tetraazidomethane participates in a number of reactions including

hydrolysis Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution, elimination, and solvation reactions in which water is the nucleophile. Biological hydrolys ...

cycloaddition reaction In organic chemistry, a cycloaddition is a chemical reaction in which "two or more unsaturated molecules (or parts of the same molecule) combine with the formation of a cyclic adduct in which there is a net reduction of the bond multiplicity". T ...

s with

alkene In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond. Alkene is often used as synonym of olefin, that is, any hydrocarbon containing one or more double bonds.H. Stephen Stoker (2015): General, Organic, an ...

s and alkynes, and reaction with

phosphine Phosphine (IUPAC name: phosphane) is a colorless, flammable, highly toxic compound with the chemical formula , classed as a pnictogen hydride. Pure phosphine is odorless, but technical grade samples have a highly unpleasant odor like rotting ...

s to form

phosphazene Phosphazenes refer to classes of organophosphorus compounds featuring phosphorus(V) with a double bond between P and N. One class of phosphazenes have the formula . These phosphazenes are also known as iminophosphoranes and phosphine imides. They a ...

References

{{Azides Organoazides Explosive chemicals