stringtranslate.com

Tosyl azide

Tosyl azide is a reagent used in organic synthesis.[1]

Uses

Tosyl azide is used for the introduction of azide and diazo functional groups.[1] It is also used as a nitrene source and as a substrate for [3+2] cycloaddition reactions.[1]

Preparation

Tosyl azide can be prepared by the reaction of tosyl chloride with sodium azide in aqueous acetone.[2]

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.[1]

See also

References

  1. ^ a b c d e Heydt, H.; Regitz, M.; Mapp, A. K.; Chen, B. (2008). "P-Toluenesulfonyl Azide". p -Toluenesulfonyl Azide. Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rt141.pub2. ISBN 978-0-471-93623-7.
  2. ^ Curphey, T. J. (1981). "Preparation of p-Toluenesulfonyl Azide. A Cautionary Note". Organic Preparations and Procedures International. 13 (2): 112–115. doi:10.1080/00304948109356105.