Trifluoromethanesulfonic anhydride, 98%
|UN#:||UN3265||Hazard Class:||8||Packing Group:||II|
|Alternate Name:||Triflic anhydride|
Pricing and Availability
|Formula weight:||282.13||Refractive Index:||1.3210|
|Melting point:||-80°||Sensitivity:||Moisture Sensitive|
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).
|Harmonized Tariff Code:||2904.90|
GHS Hazard and Precautionary Statements
Causes severe skin burns and eye damage. Causes serious eye damage.
Do not breathe dust/fume/gas/mist/vapours/spray. 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.
Risk & Safety
|Reacts violently with water. Causes burns.|
|Keep container dry. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Never add water to this product. Wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show the label where possible). This material and/or its container must be disposed of as hazardous waste.|