Methane sulfonyl azide Property

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

Hazard and Precautionary Statements (GHS)

Methane sulfonyl azide Chemical Properties,Usage,Production

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.