Trifluoromethanesulfonic anhydride

• CAS: 358-23-6
• Catalog Number: ACM358236
• Category: Sulfonylation Reagents
• Molecular Weight: 282.14
• Molecular Formula: C2F6O5S2
• Synonyms: Triflic anhydride
• IUPAC Name: trifluoromethylsulfonyl trifluoromethanesulfonate
• 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.)
• 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: 1
• EC Number: 206-616-8
• Exact Mass: 281.909134g/mol
• Formal Charge: 0
• H-Bond Acceptor: 11
• H-Bond Donor: 0
• Heavy Atom Count: 15
• Monoisotopic Mass: 281.909134g/mol
• Physical State: Liquid
• Rotatable Bond Count: 2
• UNII: 8W034LHG1U
• XLogP3: 1.6