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Tosyl azide

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Chemical compound used in organic synthesis
Tosyl azide
Names
Preferred IUPAC name 4-Methylbenzene-1-sulfonyl azide
Other names p-Toluenesulfonyl azide; p-Tosyl azide; p-Toluenesulfonazide; TsN3
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.012.164 Edit this at Wikidata
EC Number
  • 213-381-5
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C7H7N3O2S/c1-6-2-4-7(5-3-6)13(11,12)10-9-8/h2-5H,1H3
SMILES
  • O=S(=O)(#N)c1ccc(cc1)C
Properties
Chemical formula C7H7N3O2S
Molar mass 197.21 g·mol
Appearance Oily colorless liquid
Density 1.286 g/cm
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 , 100 kPa). Infobox references
Chemical compound

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 cycloaddition reactions.

Preparation

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

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

References

  1. ^ 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.
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