Methyl azide

Methyl azide
Skeletal formula of methyl azide
Ball-and-stick model of the methyl azide molecule
Space-filling model of the methyl azide molecule
Names
Preferred IUPAC name
Azidomethane
Identifiers
3D model (JSmol)
ChemSpider
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).
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Infobox references

Methyl azide is a covalent molecule related to hydrazoic acid and other alkyl azides.

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

  1. ↑ Dimroth, O.; Wislicenus, W. (1905). "Ueber das Methylazid". Berichte der Deutschen Chemischen Gesellschaft. 38 (2): 1573–1576. doi:10.1002/cber.19050380254.
  2. ↑ 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.
  3. ↑ 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.
  4. ↑ Urben, P. G., ed. (2006). Bretherick's Handbook of Reactive Chemical Hazards (7th ed.). Elsevier. ISBN 9780123725639.
  • Graner, G.; Hirota, E.; Iijima, T.; Kuchitsu, K.; Ramsay, D. A.; Vogt, J.; Vogt, N. "CH3N3 Methyl azide". In Kuchitsu, K. 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.
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