Trifluoromethanesulfonyl azide

Solubility soluble in most organic solvents, e.g. hexane, de-calin, dichloromethane, THF, dioxane, acetone, MeCN, DMF, DMSO, MeOH. 

Analysis of Reagent Purity IR, Raman, F-NMR, MS, UV other analysis gas electron diffraction.  

Preparative Methods from Tf20 and NaNs in H20/CH2Cl2, Tf20 andNaNs in H20/catalystBu4NHS04/hexane, TfF and NaNs in MeOH, or TfCl and NaNs in MeCN.  

Purification distillation at reduced pressure (CAUTION ). Handling, Storage, and Precautions prepared in situ as a solution in dichloromethane, hexane, MeCN, or CICH2CH2CI. Solutions in dichloromethane are stable at -14°C for several weeks solutions in hexane are stable at4 °C for several days. Neat TfNs is stable up to 100 °C.  

CAUTION Preparation of TfNs in the absence of an organic solvent should be avoided as it may lead to an explosion. Reactions involving neat TfNs should always be handled behind a safety shield. 

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Another nitrogen-containing tnflate derivative, trifluoromethanesulfonyl azide, is prepared by the reaction of triflic anhydride with aqueous sodium azide [775] and is used as an efficient reagent for the synthesis of alkylazides from alkylammes (equation 58)... 

To reduce the danger of an explosion in this reaction, trifluoromethanesulfonyl azide can be generated in methylene chloride in situ and used for subsequent transformations without isolation [775]... 

Deprotonation of the quinazolinium salt 148 with NaH or KH gave the dienamine 149 which cycloadds to methylsulfonyl azide or trifluoromethanesulfonyl azide included in the reaction to afford a mixture of two sulfonyl-imino-substituted benzodiazepine derivatives 150 and 151 after a ring expansion mediated by the expulsion of N2 (Scheme 88) <2000EJ01577>. 

Charette, A. B., Wurz, R. P., Ollevier, T. Trifluoromethanesulfonyl Azide A Powerful Reagent for the Preparation of a-Nitro-a-diazocarbonyl Derivatives. J. Org. Chem. 2000, 65, 9252-9254. 

Hakimelahi, G.H., and Just, G., Two simple methods for the synthesis of trialkyl a-aminophospho-noacetates. Trifluoromethanesulfonyl azide as an azide-transfer agent, Synth. Commun., 10, 429, 1980. 

Trifluoromethanesulfonyl azide, prepared in situ from trifluoromethanesulfonyl chloride and sodium azide in dimethylformamide, is reported to azidate phospho-noacetic esters and p-dicarbonyl compounds in the presence of triethylamine,309 whereas the same, but preformed, reagent gives the diazo compounds with a-nitro328 and a-cyano329 carbonyl compounds in the presence of pyridine. The reason for this dichotomy is not clear but because the former reaction was carried out under typical diazo transfer conditions the products may have been misidentified.330... 

A repetition of the reaction of triethyl phosphonoacetate with trifluoromethanesulfonyl azide gave exclusively the diazo transfer product rather than the azide as reported in reference 309. Charette, A. B. Marcoux, D. Department de Chimie, University de Montreal, Montreal, Canada. Personal communication, 2007. 

The synthesis of S-N-azido derivatives of N-acetylneuraminic acid has been accomplished by both enzymatic and chemical methods. In particular, SchmidP and Wong described the introduction of the azido group from known sialosyl donors 11a and 11b respectively by using trifluoromethanesulfonyl azide (triflic azide, TfNs) as the diazo transferring reagent (Scheme 3). 

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