Tosyl azide explained

Tosyl azide is a reagent used in organic synthesis.

Uses

Tosyl azide is used for the introduction of azide and diazo functional groups. It is also used as a nitrene source and as a substrate for [3+2] cycloaddition reactions.

Preparation

Tosyl azide can be prepared by the reaction of tosyl chloride with sodium azide in aqueous acetone.^[1]

Safety

Tosyl azide is one of the most stable azide compounds but is still regarded as a potential explosive and should be carefully stored, while particular caution is vital for all reactions in which it is heated at or above 100 °C. The initial temperature of the explosive decomposition is about 120 °C.

See also

• Diphenylphosphoryl azide
• Trifluoromethanesulfonyl azide

Notes and References

1. Preparation of p-Toluenesulfonyl Azide. A Cautionary Note . Curphey, T. J. . Organic Preparations and Procedures International . 1981 . 13 . 2 . 112–115 . 10.1080/00304948109356105 .