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91737

Sigma-Aldrich

Trifluoromethanesulfonic anhydride

purum, ≥98.0% (T)

Synonym(s):

Tf2O, Triflic anhydride

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About This Item

Linear Formula:
(CF3SO2)2O
CAS Number:
358-23-6
Molecular Weight:
282.14
Beilstein:
1813600
EC Number:
206-616-8
MDL number:
MFCD00000408
UNSPSC Code:
12352101
PubChem Substance ID:
329770073
NACRES:
NA.22

vapor density

5.2 (vs air)

Quality Level

200

vapor pressure

8 mmHg ( 20 °C)

grade

purum

Assay

≥98.0% (T)

form

liquid

refractive index

n20/D 1.321 (lit.)

bp

81-83 °C (lit.)

density

1.677 g/mL at 25 °C (lit.)

SMILES string

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

InChI

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

InChI key

WJKHJLXJJJATHN-UHFFFAOYSA-N

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Application

Catalyst for glycosylation for synthesis of polysaccharides

Reagent for stereoselective synthesis of mannosazide methyl uronate donors

Activator for direct glycosylation with anomeric hydroxy sugars
Trifluoromethanesulfonic anhydride can be used in the preparation of azido sugars such as 6-azido fucose. It can also be used as a promoter for the Friedel-Crafts acylation of aromatic compounds with carboxylic acids in the absence of catalyst.
Tf2O in combination with:
  • Diphenyl sulfoxide, forms an efficient promoter system for the activation of thioglycosides for glycosylation reactions.
  • 2-chloropyridine, can be used for secondary amide activation.
  • Potassium iodide, can effectively mediate the deoxygenation of sulfoxides to form sulfides.
  • Hydrogen peroxide, for the selective oxidation of sulfanes to sulf­oxides in the presence of oxidatively sensitive functional groups.

Tf2O can react with:
  • Ketones in the presence of a base to form vinyl triflates.
  • Magnesium alkoxides to form corresponding symmetrical or unsymmetrical ethers.
  • Sodium azide for the in situ preparation of triflyl azide.

Other Notes

Electrophilic trifyl source. Reviews

Signal Word

Danger

Hazard Statements

H272,H302,H314,H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Ox. Liq. 2 - Skin Corr. 1B - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

not determinedboils before flash

Flash Point(C)

not determinedboils before flash

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Synthesis of pyrimidines by direct condensation of amides and nitriles.
Movassaghi M & Hill MD.
Nature Protocols, 2(8), 2018-2018 (2007)
Synthesis, 85-85 (1982)
H2O2/Tf2O System: An efficient oxidizing reagent for selective oxidation of sulfanes.
Khodaei MM, et al.
Synthesis, 2008(11), 1682-1684 (2008)
Jeroen D C Codée et al.
Organic letters, 5(9), 1519-1522 (2003-04-26)
Diphenylsulfoxide in combination with triflic anhydride provides a very potent thiophilic glycosylation promotor system, capable of activating disarmed thioglycosides. The usefulness of this novel thiophilic activator is illustrated in a successful chemoselective glycosylation sequence in which the donor thioglycoside in
Mild and efficient deoxygenation of sulfoxides to sulfides with triflic anhydride/potassium iodide reagent system.
Bahrami K, et al.
Synthesis, 2008(16), 2543-2546 (2008)
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