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Trifluoromethanesulfonyl azide

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Trifluoromethanesulfonyl azide
Names
Preferred IUPAC name Trifluoromethanesulfonyl azide
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/CF3N3O2S/c2-1(3,4)10(8,9)7-6-5Key: NQPHMXWPDCSHTE-UHFFFAOYSA-N
  • InChI=1/CF3N3O2S/c2-1(3,4)10(8,9)7-6-5Key: NQPHMXWPDCSHTE-UHFFFAOYAT
SMILES
  • FC(F)(F)S(=O)(=O)N==
Properties
Chemical formula CF3SO2N3
Molar mass 175.09 g·mol
Melting point 80-81 °C
Solubility in water insoluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Trifluoromethanesulfonyl azide or triflyl azide CF3SO2N3 is an organic azide used as a reagent in organic synthesis.

Preparation

Trifluoromethanesulfonyl azide is prepared by treating trifluoromethanesulfonic anhydride with sodium azide, traditionally in dichloromethane. However, the use of dichloromethane is avoided since it can generate highly explosive azido-chloromethane and diazidomethane. The reaction may also instead be conducted in toluene, acetonitrile, or pyridine.

Tf2O + NaN3 → TfN3 + NaOTf (Tf = CF3SO2)

An alternative route starts from imidazole-1-sulfonyl azide.

Reactions

Trifluoromethanesulfonyl azide generally converts amines to azides.

See also

References

  1. ^ C. J. Cavender & V. J. Shiner (1972). "Trifluoromethanesulfonyl azide. Its reaction with alkyl amines to form alkyl azides". The Journal of Organic Chemistry. 37 (22): 3567–3569. doi:10.1021/jo00795a052.
  2. Bernet, Bruno; Vasella, Andrea; Liu, Qi; Tor, Yitzhak (2009). "Trifluoromethanesulfonyl Azide". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rn00114.pub2. ISBN 978-0-471-93623-7.
  3. Titz, A.; Radic, Z.; Schwardt, O.; Ernst, B. Tetrahedron Lett. (2006), 47, 2383.
  4. R.-B. Yan, F. Yang, Y. Wu, L.-H. Zhang and X.-S. Ye (2005). "An efficient and improved procedure for preparation of triflyl azide and application in catalytic diazotransfer reaction". Tetrahedron Letters. 46 (52): 8993–8995. doi:10.1016/j.tetlet.2005.10.103.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  5. E. D. Goddard-Borger & R. V. Stick (2007). "An Efficient, Inexpensive, and Shelf-Stable Diazotransfer Reagent:  Imidazole-1-sulfonyl Azide Hydrochloride". Organic Letters. 9 (19): 3797–3800. doi:10.1021/ol701581g. PMID 17713918.
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