Methanesulfonyl azide
Chemical compound
From Wikipedia, the free encyclopedia
Methanesulfonyl azide is the azide of methanesulfonic acid. It is used as a reagent for the production of diazo compounds.
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| Names | |
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| Other names
Mesyl azide | |
| Identifiers | |
3D model (JSmol) |
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CompTox Dashboard (EPA) |
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| Properties | |
| CH3N3O2S | |
| Molar mass | 121.12 g·molâ1 |
| Melting point | 18 °C (64 °F; 291 K) |
| Boiling point | 120 °C (248 °F; 393 K) decomposes |
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
Methanesulfonyl azide can be prepared from methanesulfonyl chloride by reaction with sodium azide in ethanol[1] or methanol,[2] Preparation in situ is also possible, for example in acetonitrile, and is advantageous to avoid explosion hazards.[3]
Properties
Methanesulfonyl azide melts at 18 °C and decomposes from 120 °C.[1] Like many other azides, it is explosive.[3] At low temperature, methanesulfonyl azide crystallizes in the triclinic crystal system in the space group P1 with the lattice parameters a = 5.6240 à ; b = 5.9498 à , c = 7.6329 à , α = 72.216°, β = 70.897°, and γ = 88.601°, and two molecules per unit cell.[1]
Mesyl azide is an antidote for hydrogen sulfide poisoning in mice.[4]
Reactions
Methanesulfonyl azide is part of the sulfonyl azides, a family of reagents for diazo transfer. Within the family, methanesulfonyl azide has particularly simple, inexpensive production and a straightforward purification of the reaction mixture.[2]
The photolysis of methanesulfonyl azide in a matrix of argon or neon yields a short-lived nitrene.[1] If methanesulfonyl azide is irradiated in the presence of a hydrocarbon, methanesulfonyl amide is formed, as well as N-substituted derivatives by reaction with the hydrocarbon.[5]