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

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A11767
Trifluoromethanesulfonic anhydride, 98%

CAS: 358-23-6 MDL: MFCD00000408  EINECS: 206-616-8
UN#:UN3265Hazard Class:8Packing Group:II
Alternate Name: Triflic anhydride

 

Pricing and Availability

Size ($) Price Your Price Quantity Options Availability
10g 48.30 Check Availability Add to Favorites Enter qty and click checkbox
25g 99.70 Check Availability Add to Favorites Enter qty and click checkbox
50g 173.00 Check Availability Add to Favorites Enter qty and click checkbox
100g 323.00 Check Availability Add to Favorites Enter qty and click checkbox
250g 442.00 Check Availability Add to Favorites Enter qty and click checkbox


Chemical Properties

Formula: C2F6O5S2  Density: 1.720
Formula weight: 282.13  Refractive Index: 1.3210
Melting point: -80° Sensitivity: Moisture Sensitive
Boiling point: 81-83° 

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).


Other References

Beilstein: 1813600
UN#: UN3265
Harmonized Tariff Code: 2904.90

GHS Hazard and Precautionary Statements

Hazard Statements : H314-H318

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

Precautionary Statements : P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A

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.

Corrosive

Risk & Safety

Risk Phrases: 14-34
Reacts violently with water. Causes burns.
Safety Phrases: 8-26-30-36/37/39-45-60
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.
Corrosive
TSCA: Yes
RTECS: PB2772000