Tetraazidomethane

Tetraazidomethane
Tetraazidomethane
Tetraazidomethane
Tetraazidomethane
Tetraazidomethane
Names
Preferred IUPAC name
Tetraazidomethane
Identifiers
CAS Number
  • 869384-16-7 ☒N
3D model (JSmol)
  • Interactive image
ChemSpider
  • 17219283 checkY
PubChem CID
  • 16059578
CompTox Dashboard (EPA)
  • DTXSID20581604 Edit this at Wikidata
InChI
  • InChI=1S/CN12/c2-10-6-1(7-11-3,8-12-4)9-13-5 checkY
    Key: PGNZIEKVQCKOBT-UHFFFAOYSA-N checkY
  • InChI=1/CN12/c2-10-6-1(7-11-3,8-12-4)9-13-5
    Key: PGNZIEKVQCKOBT-UHFFFAOYAX
  • [N-]=[N+]=N\C(\N=[N+]=[N-])(\N=[N+]=[N-])\N=[N+]=[N-]
Properties
Chemical formula
 C(N3)4
Molar mass 180.095 g·mol−1
Appearance Colorless liquid
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
Chemical compound

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

References

  1. ^ 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
  2. ^ "Tetraazidomethane: Chemistry with a Bang", Chemical & Engineering News, Dec. 18, 2006, 46.
  • v
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Salts and covalent derivatives of the azide ion
HN3 He
LiN3 Be(N3)2 B(N3)3 CH3N3
C(N3)4
CO(N3)2 		NH4N3
N3NO
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(N3)5 Se(N3)4 BrN3 Kr
RbN3 Sr(N3)2 Y(N3)3 Zr(N3)4 Nb Mo Tc Ru(N3)63− Rh(N3)63− Pd(N3)2 AgN3 Cd(N3)2 In Sn Sb(N3)5 Te(N3)4 IN3 Xe(N3)2
CsN3 Ba(N3)2 * Lu(N3)3 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 ** Lr Rf Db Sg Bh Hs Mt Ds Rg Cn Nh Fl Mc Lv Ts Og
 
* La(N3)3 Ce(N3)3
Ce(N3)4 		Pr Nd Pm Sm(N3)3 Eu(N3)2
Eu(N3)3 		Gd(N3)3 Tb Dy(N3)3 Ho(N3)3 Er Tm Yb(N3)3
** Ac(N3)3 Th(N3)4 Pa UO2(N3)2 Np Pu Am Cm Bk Cf Es Fm Md No