[A11767] CAS 358-23-6 | Trifluoromethanesulfonic anhydride, 98%

CAS : 358-23-6
UN# : UN3098
MDL : MFCD00000408
Hazard Class : 5.1
EINECS : 206-616-8
Packing Group : II

Other name :

Triflic anhydride

Chemical Properties

Formula : C2F6O5S2
Formula weight : 282.13
Melting Point : -80°
Boiling Point : 81-83°
Density : 1.720
Refractive Index : 1.3210
Sensitivity : Moisture Sensitive. Ambient temperatures.
Form : Liquid
Solubility : Miscible with dichloromethane. Immiscible with hydrocarbons.

Literature 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).

Notes

Moisture sensitive. Incompatible with water, strong bases, strong oxidizing agents, acids and alcohols.Other References:Beilstein: 1813600UN#: UN3098

Grade Specifications

Grade Specifications

Hazard Statements : H314-H318Causes severe skin burns and eye damage.Causes serious eye damage.
Precautionary Statements : P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501aDo 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.