Tosyl azide
Names
Preferred IUPAC name
4-Methylbenzene-1-sulfonyl azide
Other names
p-Toluenesulfonyl azide; p-Tosyl azide; p-Toluenesulfonazide; TsN3
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.012.164
EC Number
  • 213-381-5
UNII
  • InChI=1S/C7H7N3O2S/c1-6-2-4-7(5-3-6)13(11,12)10-9-8/h2-5H,1H3
  • O=S(=O)([N-][N+]#N)c1ccc(cc1)C
Properties[1]
C7H7N3O2S
Molar mass 197.21 g·mol−1
Appearance Oily colorless liquid
Density 1.286 g/cm3
Melting point 21 to 22 °C (70 to 72 °F; 294 to 295 K)
Boiling point 110 to 115 °C (230 to 239 °F; 383 to 388 K) at 0.001 mmHg
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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. 1 2 3 4 5 Heydt, H.; Regitz, M.; Mapp, A. K.; Chen, B. (2008). "P-Toluenesulfonyl Azide". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rt141.pub2. ISBN 978-0471936237.
  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.
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