Tetraazidomethane

Tetraazidomethane
Names
	Preferred IUPAC name Tetraazidomethane
Identifiers
CAS Number	869384-16-7 ;
3D model (JSmol)	Interactive image;
ChemSpider	17219283 ;
PubChem CID	16059578;
CompTox Dashboard (EPA)	DTXSID20581604 ;
	InChI InChI=1S/CN12/c2-10-6-1(7-11-3,8-12-4)9-13-5 Key: PGNZIEKVQCKOBT-UHFFFAOYSA-N ; InChI=1/CN12/c2-10-6-1(7-11-3,8-12-4)9-13-5 Key: PGNZIEKVQCKOBT-UHFFFAOYAX;
	SMILES [N-]=[N+]=N\C(\N=[N+]=[N-])(\N=[N+]=[N-])\N=[N+]=[N-];
Properties
Chemical formula	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

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

Synthesis[]

It was first prepared by Klaus Banert in 2006 by reaction of trichloroacetonitrile with sodium azide.^[1]

Uses[]

As with other , 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 reactions including hydrolysis, cycloaddition reactions with alkenes and alkynes, and reaction with phosphines to form phosphazenes.^[1]

References[]

^ ^a ^b "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
^ "Tetraazidomethane: Chemistry with a Bang", Chemical & Engineering News, Dec. 18, 2006, 46.

[Banert-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.

[1]

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