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358-23-6 - Trifluoromethanesulfonic anhydride, 98% - Triflic anhydride - A11767 - Alfa Aesar

A11767 Trifluoromethanesulfonic anhydride, 98%

Numéro de CAS
Triflic anhydride

Conditionnement Prix ($) Quantité Disponibilité
10g 50,50
25g 104,00
50g 179,00
100g 326,00
250g 458,00
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Trifluoromethanesulfonic anhydride, 98%


Propriétés chimiques

Poids moleculaire
Point de fusion
Point d'ébullition
Indice de réfraction
Moisture Sensitive
Miscible with dichloromethane. Immiscible with hydrocarbons.


Trifluoromethanesulfonic anhydride is used to convert phenols and imine into triflic ester and NTf group. It is a strong electrophile used for the introduction of triflyl group in chemical synthesis. It serves as a reagent in the preparation of alkyl and vinyl triflates, and for the stereoselective synthesis of mannosazide methyl uronate donors. It acts as a catalyst for glycosylation with anomeric hydroxy sugars to prepare polysaccharides.


Moisture sensitive. Incompatible with water, strong bases, strong oxidizing agents, acids and alcohols.

Références bibliographiques

For examples of preparation of alkyl and aryl triflates, and use of the latter in the Stille coupling reaction, see: Org. Synth. Coll., 6, 324 (1988); 9, 553 (1998). Alkyl triflates undergo solvolysis reactions between five and seven powers of ten times more rapidly than the corresponding halides or tosylates: J. Am. Chem. Soc., 97, 6478 (1975); Angew. Chem. Int. Ed., 9, 521 (1970). For a review of the chemistry of triflate esters, see: Synthesis, 85 (1982).

Enolizable carbonyl compounds in the presence of base can be converted to vinyl (enol) triflates: Synthesis, 85 (1982); Org. Synth. Coll., 6, 757 (1988). For conditions employing preferred base, 2,6-Di-tert-butyl-4-methyl­pyridine, L14143, see: Org. Synth. Coll., 8, 97, 126 (1993). Enol triflates behave as a source of vinyl cations. For reviews, see: Angew. Chem. Int. Ed., 17, 333 (1978); Acc. Chem. Res., 11, 107 (1978); 15, 348 (1982); 21, 147 (1988).

For formation of keteniminium triflates, see N,N-Dimethyl­acetamide, A10924.

The Ritter reaction is normally most successful with tertiary alcohols. In contrast, a useful variation allows conversion of primary or secondary alcohols to amides in good yield: Tetrahedron Lett., 30, 581 (1989):

For use in the Vilsmeier formylation of less active substrates, see N,N-Dimethyl­formamide, A13547.

Triflic anhydride has also been found to promote the nitration of arenes, even deactivated ones, under mild conditions: Synthesis, 1087 (1992).

For a review of chemical transformations induced by the reagent, see: Tetrahedron, 56, 3077 (2000). For a brief feature on uses in synthesis, see: Synlett, 390 (2004).

Dadgar, M.; Kalkhorani, N. M. Efficient and practical one-pot route to synthesise quinazolin4 (3H)-ones using trifluoromethanesulfonic anhydride and 2-chloropyridine. J. Chem. Res. 2015, 39 (2), 120-122.

Huang, P. Q.; Lang, Q. W.; Wang, A. E.; Zheng, J. F. Direct reductive coupling of secondary amides: chemoselective formation of vicinal diamines and vicinal amino alcohols. Chem. Commun. 2015, 51 (6), 1096-1099.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H314-H318

Causes severe skin burns and eye damage. Causes serious eye damage.

Mentions de prudence: P260u-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501a

IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Autres références

Classe de danger
Groupe d'emballage
Code tarifaire harmonisé


Consulté récemment

Produits chimiques

Sciences de la vie

Métaux et matériaux


Analytique et matériel de laboratoire