Methyl azide

Methyl azide
Other names azidomethane
Identifiers
PubChem	79079
ChemSpider	71411 Y
Jmol-3D images	Image 1
SMILES [N-]=[N+]=N\C
InChI InChI=1S/CH3N3/c1-3-4-2/h1H3 Y Key: PBTHJVDBCFJQGG-UHFFFAOYSA-N Y
Properties
Molecular formula	CH3N3
Molar mass	57.05
Explosive data
Shock sensitivity	High
Friction sensitivity	High
Hazards
Main hazards	Harmful, Explosive
Related compounds
Related compounds	Hydrazoic acid, Chlorine azide, Ethyl azide
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Methyl azide CH₃N₃, is a covalent molecule related to hydrazoic acid and other alkyl azides. Methyl azide is a linear molecule. In resonance the central nitrogen is clearly linear (two electron groups), but the nitrogen bonded to H₃C, has three electron groups in H₃C-N=N⁺=N^- ⇔ H₃C-N^--N⁺≡N . ^[1]

It can be prepared by a methylation of sodium azide. The first synthesis was reported in 1905. ^[2] It decomposes in a first-order reaction CH₃N₃ → CH₃N + N₂ ^[3]

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. ^[4]

Safety Precautions

Methyl azide is stable at ambient temperature but may explode when heated. ^[5] 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

1. ^ Pauling, Linus, Brockway, O.; The Adjacent Charge Rule and the Structure of Methyl Azide, Methyl nitrate, and Fluorine nitrate; JACS, 1937, 59 (1), pp 13-20 DOI:10.1021/ja01280a005
2. ^ Dimroth, O. and Wislicenus, W.; Chemische Berichte ; 38, 1573 (1905)
3. ^ O'Dell, M.S. and Darwent B. Thermal decomposition of methyl azideCanadian Journal of Chemistry, 48, 1140 (1970)
4. ^ Alfredo Quinto-Hernandez and Alec M. Wodtke, Department of Chemistry and Biochemistry, University of California, Santa Barbara; Chris J. Bennett, Y. Seol Kim, and Ralf I. Kaiser; Department of Chemistry, University of Hawaii at Manoa; On the Interaction of Methyl Azide (CH3N3) Ices with Ionizing Radiation: Formation of Methanimine (CH2NH), Hydrogen Cyanide (HCN), and Hydrogen Isocyanide (HNC) ; Journal of Physical Chemistry DOI: 10.1021/jp103028v Publication Date (Web): December 17, 2010
5. ^ Bretherick's handbook of reactive chemical hazards; edited by P. G. Urben

• Graner, G., Hirota, E., Iijima, T., Kuchitsu, K., Ramsay,D. A., Vogt, J., Vogt,N.: CH3N3 Methyl azide. Kuchitsu, K. (ed.). SpringerMaterials - The Landolt-Börnstein Database [1] DOI: 10.1007/10653318_320
• NIST Webbook