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A11767 Trifluoromethanesulfonic anhydride, 98%

CAS Number
358-23-6
Synonyms
Triflic anhydride

Stock No. Size Price ($) Quantity Availability
A11767-09 10g 52.80
A11767-14 25g 107.00
A11767-18 50g 187.00
A11767-22 100g 342.00
A11767-30 250g 480.00
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Trifluoromethanesulfonic anhydride, 98%

MDL
MFCD00000408
EINECS
206-616-8

Chemical Properties

Formula
C2F6O5S2
Formula Weight
282.13
Melting point
-80°
Boiling Point
81-83°
Density
1.720
Refractive Index
1.3210
Storage & Sensitivity
Moisture Sensitive. Ambient temperatures.
Solubility
Miscible with dichloromethane. Immiscible with hydrocarbons.

Applications

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.

Notes

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

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).

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.

GHS Hazard and Precautionary Statements

Hazard Statements: H290-H302-H314-H335

May be corrosive to metals. Harmful if swallowed. Causes severe skin burns and eye damage. May cause respiratory irritation.

Precautionary Statements: P234-P260-P264b-P270-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P390-P501c

Keep only in original container. Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Rinse mouth. Do NOT induce vomiting. Wash contaminated clothing before reuse. Absorb spillage to prevent material damage. Dispose of contents/ container to an approved waste disposal plant

Other References

Beilstein
1813600
Hazard Class
8
Packing Group
I
Harmonized Tariff Code
2904.99
TSCA
Yes
RTECS
PB2772000

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