Tetraazidomethane
{{redirect|CN12|cranial nerve 12|hypoglossal nerve}}
{{chembox
| Verifiedfields = changed
| verifiedrevid = 470603291
| Name = Tetraazidomethane
| ImageFileL1 = tetraazidomethane.png
| ImageSizeL1 = 120px
| ImageNameL1 = Tetraazidomethane
| ImageFileR1 = Tetraazidomethane-3D-vdW.png
| ImageSizeR1 = 120px
| ImageNameR1 = Tetraazidomethane
| PIN = Tetraazidomethane
|Section1 = {{Chembox Identifiers
| PubChem = 16059578
| InChI = 1/CN12/c2-10-6-1(7-11-3,8-12-4)9-13-5
| InChIKey = PGNZIEKVQCKOBT-UHFFFAOYAX
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/CN12/c2-10-6-1(7-11-3,8-12-4)9-13-5
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = PGNZIEKVQCKOBT-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|changed|??}}
| CASNo = 869384-16-7
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 17219283
| SMILES = [N-]=[N+]=N\C(\N=[N+]=[N-])(\N=[N+]=[N-])\N=[N+]=[N-]
}}
|Section2 = {{Chembox Properties
| Formula = {{chem2|C(N3)4}}
| C=1|N=12
| Appearance = Colorless liquid
| Density =
| BoilingPt = ~165 °C (estimate)
}}
}}
File:Tetraazidomethane-spin.gif
Tetraazidomethane, {{chem2|C(N3)4}}, is a colorless, highly explosive liquid. Its chemical structure consists of a carbon atom covalently bonded to four azide functional groups.
Synthesis
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. 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.
:File:Tetraazidomethane chemistry 01.svg{{clear-left}}