CAS 358-23-6 Trifluoromethanesulfonic anhydride

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Trifluoromethanesulfonic anhydride

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Catalog Number

ACM358236

CAS Number

358-23-6

Product Name

Trifluoromethanesulfonic anhydride

Structure

Category

Other Electronic Materials

Synonyms

Triflic anhydride

IUPAC Name

trifluoromethylsulfonyl trifluoromethanesulfonate

Molecular Weight

282.14

Molecular Formula

C2F6O5S2

Canonical SMILES

C(F)(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F

InChI

InChI=1S/C2F6O5S2/c3-1(4,5)14(9,10)13-15(11,12)2(6,7)8

InChI Key

WJKHJLXJJJATHN-UHFFFAOYSA-N

Boiling Point

81-83 °C (lit.)

Purity

99%

Density

1.677 g/mL at 25 °C (lit.)

Application

Trifluoromethanesulfonic anhydride, commonly known as triflic anhydride, serves as a highly effective reagent in various chemical transformations. It is primarily employed in converting phenols and imines into triflic esters and NTf groups, respectively. Due to its strong electrophilic nature, it is particularly valuable in the introduction of the triflyl group during chemical synthesis. This makes it essential in preparing alkyl and vinyl triflates, as well as in the stereoselective synthesis of mannosazide methyl uronate donors. Additionally, triflic anhydride acts as a catalyst in glycosylation reactions with anomeric hydroxy sugars to produce polysaccharides. As an organosulfonic anhydride, it is functionally related to triflic acid and has become a staple in synthetic chemistry due to its ability to facilitate a wide range of downstream transformations.

Complexity

370

Covalently-Bonded Unit Count

EC Number

206-616-8

Exact Mass

281.909134g/mol

Formal Charge

Heavy Atom Count

MeSH Entry Terms

triflic anhydride

Monoisotopic Mass