| Identification | Back Directory | [Name]
Methane sulfonyl azide | [CAS]
1516-70-7 | [Synonyms]
Methane sulfonyl azide
N-diazomethanesulfonamide
Methanesulfonic acid azide | [Molecular Formula]
CH3N3O2S | [MDL Number]
MFCD17013585 | [MOL File]
1516-70-7.mol |
| Chemical Properties | Back Directory | [Melting point ]
91-92 °C | [Boiling point ]
59-60 °C(Press: 17 Torr) | [density ]
1.4361 g/cm3 | [refractive index ]
1.4675 | [solubility ]
sol Et2O, MeOH, MeCN; sparingly sol 95% EtOH, cold H2O. | [Appearance]
low-melting white solid or clear, colorless oil | [InChI]
InChI=1S/CH3N3O2S/c1-7(5,6)4-3-2/h1H3 | [InChIKey]
BHQIGUWUNPQBJY-UHFFFAOYSA-N | [SMILES]
CS(N=[N+]=[N-])(=O)=O |
| Hazard Information | Back Directory | [Uses]
Methane sulfonyl azide is used as a diazo transfer reagent for activated methylene,[1] methine,[1,2] and methyl[3] groups; functionalization of double
and triple bonds. | [Preparation]
Preparative Methods of Methane sulfonyl azide: reaction of Methanesulfonyl Chloride with Sodium Azide in MeOH(EtOH)/H2O[1,3] or
acetone[2] (55-61 or 96% yields, respectively). By substituting acetone for methanol, the formation of
MeSO2OMe is avoided and the reagent is obtained in >95% purity. | [storage]
Methane sulfonyl azide should be stored in the cold and the dark. Explosive when heated above
130 °C. No experimentalists have reported any difficulty handling MsN3, but proper caution should be used,
as with all azide reagents. Use in a fume hood. | [Purification Methods]
Purification of Methane sulfonyl azide: crystallization from ether in dry-ice/acetone or from 95% EtOH at -75 °C; distillation in vacuo. | [References]
1. (a) Taber, D. F.; Ruckle, R. E.; Hennessy, M. J. JOC 1986, 51, 4077. (b) Taber, D. F.; Hennessy, M. J.; Lovey, J. P.
JOC 1992, 57, 436.
2. Danheiser, R. L.; Miller, R. F.; Brisbois, R. G.; Park, S. Z. JOC 1990, 55, 1959.
3. Shatzmiller, S.; Bercovici, S. LA 1992, 877. |
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SynAsst Chemical.
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