Methyl azide
Chemical compound
From Wikipedia, the free encyclopedia
Methyl azide is an organic compound with the formula CH3N3. It is a white solid and it is the simplest organic azide.
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| Names | |||
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| Preferred IUPAC name
Azidomethane | |||
| Identifiers | |||
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PubChem CID |
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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 |
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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Preparation and properties
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
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]