Tetraazidomethane

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

Tetraazidomethane

Tetraazidomethane Tetraazidomethane
Names
IUPAC name Tetraazidomethane
Identifiers
CAS Number	869384-16-7^N
3D model (JSmol)	Interactive image
ChemSpider	17219283^Y
PubChem CID	16059578
CompTox Dashboard (EPA)	DTXSID20581604
InChI InChI=1S/CN12/c2-10-6-1(7-11-3,8-12-4)9-13-5^Y Key: PGNZIEKVQCKOBT-UHFFFAOYSA-N^Y 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).
N verify (what is ^YN ?)
Infobox references

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. "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.

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)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)6^3−	Rh(N3)6^3−	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)6^3−	Pt(N3)6^2−	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