Trifluoromethanesulfonic anhydride

• Catalog No.: A11767
• CAS Number: 358-23-6
• M. F.: C2F6O5S2
• M. W.: 282.1388192
• Purity: 98%

SYNONYMS

• Title: 三氟甲烷磺酸酐
• IUPAC name: trifluoromethanesulfonyl trifluoromethanesulfonate
• IUPAC Traditional name: triflic anhydride
• Synonyms: Triflic anhydride

DATABASE IDS

• EC Number: 206-616-8
• CAS Number: 358-23-6
• Beilstein Number: 1813600
• MDL Number: MFCD00000408

PROPERTIES

• Purity: 98%
• Boiling Point: 81-83°C
• Density: 1.720
• Melting Point: -80°C
• Refractive Index: 1.3210
• GHS Hazard statements: H314-H318
• European Hazard Symbols: Corrosive (C)
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A
• Risk Statements: 14-34
• RTECS: PB2772000
• Safety Statements: 8-26-30-36/37/39-45-60
• Storage Warning: Moisture Sensitive
• TSCA Listed: 是
• Hazard Class: 8
• UN Number: UN3265
• Packing Group: II

REFERENCES

• 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).