Methyl azide
Methyl azide is a covalent molecule related to hydrazoic acid and other alkyl azides.
| |||
Names | |||
---|---|---|---|
Preferred IUPAC name
Azidomethane | |||
Identifiers | |||
3D model (JSmol) |
|||
ChemSpider | |||
PubChem CID |
|||
CompTox Dashboard (EPA) |
|||
| |||
| |||
Properties | |||
CH3N3 | |||
Molar mass | 57.05 | ||
Appearance | white powder | ||
slightly soluble | |||
Solubility | alkane, ether | ||
Explosive data | |||
Shock sensitivity | High | ||
Friction sensitivity | High | ||
Hazards | |||
Main hazards | Highly explosive | ||
Related compounds | |||
Related compounds |
Hydrazoic acid, Chlorine azide, Ethyl azide | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |||
Infobox references | |||
It can be prepared by a methylation of sodium azide. The first synthesis was reported in 1905.[1] It decomposes in a first-order reaction:[2]
- CH3N3 → CH3N + N2
Methyl azide might be a potential precursor in the synthesis of prebiotic molecules via nonequilibrium reactions on interstellar ices initiated by energetic galactic cosmic rays (GCR) and photons.[3]
Safety precautions
Methyl azide is stable at ambient temperature but may explode when heated.[4] Presence of mercury increases the sensitivity to shock and spark. Incompatible with (dimethyl malonate + sodium methylate); mercury; methanol; sodium azide; dimethyl sulfate; sodium hydroxide; hydrogen azide. When heated to decomposition it emits toxic fumes of NOx.
References
- Dimroth, O.; Wislicenus, W. (1905). "Ueber das Methylazid" (PDF). Berichte der Deutschen Chemischen Gesellschaft. 38 (2): 1573–1576. doi:10.1002/cber.19050380254.
- O'Dell, M. S.; Darwent, B. (1970). "Thermal decomposition of methyl azide". Canadian Journal of Chemistry. 48 (7): 1140–1147. doi:10.1139/v70-187.
- Quinto-Hernandez, A.; Wodtke, A. M.; Bennett, C. J.; Kim, Y. S.; Kaiser, R. I. (2011). "On the Interaction of Methyl Azide (CH3N3) Ices with Ionizing Radiation: Formation of Methanimine (CH2NH), Hydrogen Cyanide (HCN), and Hydrogen Isocyanide (HNC)". The Journal of Physical Chemistry A. 115 (3): 250–264. doi:10.1021/jp103028v. PMID 21162584.
- Urben, P. G., ed. (2006). Bretherick's Handbook of Reactive Chemical Hazards (7th ed.). Elsevier. ISBN 9780123725639.
External links
- Graner, G.; Hirota, E.; Iijima, T.; Kuchitsu, K.; Ramsay, D. A.; Vogt, J.; Vogt, N. "CH3N3 Methyl azide". In Kuchitsu, K. (ed.). Group II Molecules and Radicals: Numerical Data and Functional Relationships in Science and Technology. 25 B. doi:10.1007/10653318_320.
- "Methyl azide". NIST Webbook. National Institute for Standards and Technology.
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 |