Tetraazidomethane

• Kohlenstofftetraazid

Colorless liquid

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Tetraazidomethane is a thermally unstable carbon-nitrogen compound having a nitrogen content of 93.3 %. Formally, it is the Tetraazidoderivat of methane. The high-energy, prone to spontaneous explosive decomposition substance was first made in 2006 by a group at the TU Chemnitz.

Representation and extraction

The synthesis of tetraazidomethane achieved by the reaction of trichloroacetonitrile with sodium azide in acetonitrile.

A second production variant starts from Triazidocarbeniumhexachloroantimonat [C (N3 ) 3] SbCl6, which gives the target compound in a reaction with sodium azide.

Properties

Pure tetraazidomethane is a colorless liquid, which tends to be extremely dangerous to spontaneous explosions. In addition to thermal instability, the compound is extremely sensitive to mechanical stress.

In solution, the link will open up some interesting synthesis reactions, such as hydrolysis to Kohlensäurediazid, cycloaddition reactions with alkenes and alkynes as well as reactions with phosphines. Strong Lewis acid such as antimony pentachloride columns from azide anion to form the corresponding Triazidocarbeniumsalzes [C (N3) 3] [ SbCl5N3 ].

Use

A practical use of free tetraazidomethane is excluded because of the high instability. In formulations, a potential for energetic mixtures is seen.