Methyl azide
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| Preferred IUPAC name
Azidomethane | |||
| Identifiers | |||
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CompTox Dashboard (EPA)
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| Properties | |||
| CH3N3 | |||
| Molar mass | 57.056 g·mol−1 | ||
| Appearance | white powder | ||
| Boiling point | 20–21 °C (68–70 °F; 293–294 K) | ||
| slightly soluble | |||
| Solubility | alkane, ether | ||
| Explosive data | |||
| Shock sensitivity | High | ||
| Friction sensitivity | High | ||
| Hazards | |||
| Occupational safety and health (OHS/OSH): | |||
Main hazards
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Highly explosive | ||
| Related compounds | |||
Related compounds
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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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Methyl azide is an organic compound with the formula CH3N3. It is a white solid and it is the simplest organic azide.
Preparation and properties
[edit]Methyl azide can be prepared by the methylation of sodium azide, for instance with dimethyl sulfate in alkaline solution, followed by passing through a tube of anhydrous calcium chloride or sodium hydroxide to remove contaminating hydrazoic acid.[1] The first synthesis was reported in 1905.[2]
Decomposition to a nitrene is a first-order reaction:
- CH3N3 → CH3N + N2
The product, like its notional tautomer methanimine, polymerizes at room temperature.[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
[edit]Methyl azide is stable at ambient temperature but may explode when heated or disturbed.[1] Presence of mercury increases the sensitivity to shock and spark. It is incompatible with methanol and dimethyl malonate.[5] When heated to decomposition, it emits toxic fumes of NO
x.[citation needed] It can be stored indefinitely in the dark at −80 °C.[1]
References
[edit]- ^ a b c Chae, Junghyun (2008-03-14), "Methyl Azide", in John Wiley & Sons, Ltd (ed.), Encyclopedia of Reagents for Organic Synthesis, Chichester, UK: John Wiley & Sons, Ltd, pp. rn00795, doi:10.1002/047084289x.rn00795, ISBN 978-0-471-93623-7
- ^ Dimroth, O.; Wislicenus, W. (1905). "Ueber das Methylazid". 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
[edit]- Graner, G.; Hirota, E.; Iijima, T.; Kuchitsu, K.; Ramsay, D. A.; Vogt, J.; Vogt, N. (1999). "CH3N3 Methyl azide". In Kuchitsu, K. (ed.). Group II Molecules and Radicals: Numerical Data and Functional Relationships in Science and Technology. Landolt-Börnstein - Group II Molecules and Radicals. Vol. 25 B. p. 1. doi:10.1007/10653318_320. ISBN 3-540-63645-5.
- "Methyl azide". NIST Webbook. National Institute for Standards and Technology.