Trifluoromethanesulfonyl azide
{{Chembox
| Verifiedfields = changed
| verifiedrevid = 470614537
| ImageFile = Trifluoromethanesulfonyl azide.png
| ImageSize = 150px
| ImageFileR1 = Trifluoromethanesulfonyl azide Space Fill.png
| ImageSizeR1 = 150px
| ImageFileL1 = Trifluoromethanesulfonyl azide Ball and Stick.png
| ImageSizeL1 = 175px
| PIN = Trifluoromethanesulfonyl azide
| OtherNames =
|Section1={{Chembox Identifiers
| InChI = 1/CF3N3O2S/c2-1(3,4)10(8,9)7-6-5
| InChIKey = NQPHMXWPDCSHTE-UHFFFAOYAT
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/CF3N3O2S/c2-1(3,4)10(8,9)7-6-5
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = NQPHMXWPDCSHTE-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|changed|??}}
| CASNo = 3855-45-6
| PubChem = 10986786
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 9161983
| SMILES = FC(F)(F)S(=O)(=O)N=[N+]=[N-]
}}
|Section2={{Chembox Properties
| Formula = {{chem2|CF3SO2N3}}
| C=1|F=3|S=1|O=2|N=3
| Appearance =
| Density =
| MeltingPt =
| BoilingPt = 80-81 °C
}}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
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Trifluoromethanesulfonyl azide or triflyl azide {{chem2|CF3SO2N3}} is an organic azide used as a reagent in organic synthesis.{{cite book |doi=10.1002/047084289X.rn00114.pub2 |chapter=Trifluoromethanesulfonyl Azide |title=Encyclopedia of Reagents for Organic Synthesis |date=2009 |last1=Bernet |first1=Bruno |last2=Vasella |first2=Andrea |last3=Liu |first3=Qi |last4=Tor |first4=Yitzhak |isbn=978-0-471-93623-7 }}
Preparation
Trifluoromethanesulfonyl azide is prepared by treating trifluoromethanesulfonic anhydride with sodium azide, traditionally in dichloromethane.{{cite journal |author1=C. J. Cavender |author2=V. J. Shiner |name-list-style=amp | title = Trifluoromethanesulfonyl azide. Its reaction with alkyl amines to form alkyl azides | journal = The Journal of Organic Chemistry | volume = 37 | issue = 22 | pages = 3567–3569 | doi = 10.1021/jo00795a052 | year = 1972}} 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,Titz, A.; Radic, Z.; Schwardt, O.; Ernst, B. Tetrahedron Lett. (2006), 47, 2383. acetonitrile, or pyridine.{{cite journal | author = R.-B. Yan, F. Yang, Y. Wu, L.-H. Zhang and X.-S. Ye | title = An efficient and improved procedure for preparation of triflyl azide and application in catalytic diazotransfer reaction | journal = Tetrahedron Letters | volume = 46 | issue = 52 | pages = 8993–8995 | doi = 10.1016/j.tetlet.2005.10.103 | year = 2005}}
:{{chem2|Tf2O + NaN3 → TfN3 + NaOTf}} (Tf = {{chem2|CF3SO2}})
An alternative route starts from imidazole-1-sulfonyl azide.{{cite journal |author1=E. D. Goddard-Borger |author2=R. V. Stick |name-list-style=amp | title = An Efficient, Inexpensive, and Shelf-Stable Diazotransfer Reagent: Imidazole-1-sulfonyl Azide Hydrochloride | journal = Organic Letters | volume = 9 | issue = 19 | pages = 3797–3800 | doi = 10.1021/ol701581g | pmid = 17713918 | year = 2007}}
Reactions
Trifluoromethanesulfonyl azide generally converts amines to azides.