Tetraazidomethane

Tetraazidomethane
Names
	IUPAC name Tetraazidomethane
Identifiers
CAS Number	869384-16-7 ;
3D model (JSmol)	Interactive image;
ChemSpider	17219283 ;
PubChem CID	16059578;
	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 polyazides, 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 surprising reactions including hydrolysis, cycloaddition reactions with alkenes and alkynes, and reaction with phosphines to form phosphazenes.^[1]

References

1 2 "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.

Salts and covalent derivatives of the azide ion
HN₃																	He
LiN₃	Be(N₃)₂											B(N₃)₃	CH₃N₃, C(N₃)₄	N(N₃)₃,H₂N—N₃	O	FN₃	Ne
NaN₃	Mg(N₃)₂											Al(N₃)₃	Si(N₃)₄	P	SO₂(N₃)₂	ClN₃	Ar
KN₃	Ca(N₃)₂	Sc(N₃)₃	Ti(N₃)₄	VO(N₃)₃	Cr(N₃)₃, CrO₂(N₃)₂	Mn(N₃)₂	Fe(N₃)₃	Co(N₃)₂, Co(N₃)₃	Ni(N₃)₂	CuN₃, Cu(N₃)₂	Zn(N₃)₂	Ga(N₃)₃	Ge	As	Se(N₃)₄	BrN₃	Kr
RbN₃	Sr(N₃)₂	Y	Zr(N₃)₄	Nb	Mo	Tc	Ru(N₃)₆³⁻	Rh(N₃)₆³⁻	Pd(N₃)₂	AgN₃	Cd(N₃)₂	In	Sn	Sb	Te	IN₃	Xe(N₃)₂
CsN₃	Ba(N₃)₂		Hf	Ta	W	Re	Os	Ir(N₃)₆³⁻	Pt(N₃)₆²⁻	Au(N₃)₄⁻	Hg₂(N₃)₂, Hg(N₃)₂	TlN₃	Pb(N₃)₂	Bi(N₃)₃	Po	At	Rn
Fr	Ra(N₃)₂		Rf	Db	Sg	Bh	Hs	Mt	Ds	Rg	Cn	Nh	Fl	Mc	Lv	Ts	Og
		↓
		La	Ce(N₃)₃, Ce(N₃)₄	Pr	Nd	Pm	Sm	Eu	Gd(N₃)₃	Tb	Dy	Ho	Er	Tm	Yb	Lu
		Ac	Th	Pa	UO₂(N₃)₂	Np	Pu	Am	Cm	Bk	Cf	Es	Fm	Md	No	Lr

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[Banert-1] 1 2 "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.