Trifluoromethanesulfonyl azide

Trifluoromethanesulfonyl azide

Names
Preferred IUPAC name Trifluoromethanesulfonyl azide
Identifiers
CAS Number	3855-45-6^N
3D model (JSmol)	Interactive image
ChemSpider	9161983^Y
PubChem CID	10986786
CompTox Dashboard (EPA)	DTXSID70450816
InChI InChI=1S/CF3N3O2S/c2-1(3,4)10(8,9)7-6-5^Y Key: NQPHMXWPDCSHTE-UHFFFAOYSA-N^Y InChI=1/CF3N3O2S/c2-1(3,4)10(8,9)7-6-5 Key: NQPHMXWPDCSHTE-UHFFFAOYAT
SMILES FC(F)(F)S(=O)(=O)N=[N+]=[N-]
Properties
Chemical formula	CF3SO2N3
Molar mass	175.09 g·mol^−1
Melting point	80-81 °C
Solubility in water	insoluble[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Trifluoromethanesulfonyl azide or triflyl azide CF₃SO₂N₃ is an organic azide used as a reagent in organic synthesis.^[2]

Preparation

Trifluoromethanesulfonyl azide is prepared by treating trifluoromethanesulfonic anhydride with sodium azide, traditionally in dichloromethane.^[1] 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,^[3] acetonitrile, or pyridine.^[4]

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

An alternative route starts from imidazole-1-sulfonyl azide.^[5]

Reactions

Trifluoromethanesulfonyl azide generally converts amines to azides.

See also

• Tosyl azide
• Diphenylphosphoryl azide
• Sulfuryl diazide

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.
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.