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

azide In chemistry, azide (, ) is a linear, polyatomic anion with the formula and structure . It is the conjugate base of hydrazoic acid . Organic azides are organic compounds with the formula , containing the azide functional group. The dominant ...

functional group In organic chemistry, a functional group is any substituent or moiety (chemistry), moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions r ...

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 of ...

with

sodium azide Sodium azide is an inorganic compound with the formula . This colorless salt is the gas-forming component in some car airbag systems. It is used for the preparation of other azide compounds. It is highly soluble in water and is acutely poisonou ...

."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 reaction, substitution, elimination reaction, elimination, and solvation reactions in which water ...

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, or olefin, is a hydrocarbon containing a carbon–carbon double bond. The double bond may be internal or at the terminal position. Terminal alkenes are also known as Alpha-olefin, α-olefins. The Internationa ...

s and

alkyne \ce \ce Acetylene \ce \ce \ce Propyne \ce \ce \ce \ce 1-Butyne In organic chemistry, an alkyne is an unsaturated hydrocarbon containing at least one carbon—carbon triple bond. The simplest acyclic alkynes with only one triple bond and n ...

s, 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 various 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 ...

s. :

References

{{Azides Organoazides Explosive chemicals