91737

Trifluoromethanesulfonic anhydride

purum, ≥98.0% (T)

• Synonym(s): Tf₂O, Triflic anhydride
• 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

Properties

• 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

Description

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

Safety Information

• Pictograms: GHS03,GHS05,GHS07
• Signal Word: Danger
• Hazard Statements: H272 - H302 - H314 - H335
• Precautionary Statements: P210 - P220 - P280 - P301 + P312 - P303 + P361 + P353 - P305 + P351 + P338
• Hazard Classifications: Acute Tox. 4 Oral - Eye Dam. 1 - Ox. Liq. 2 - Skin Corr. 1B - STOT SE 3
• Target Organs: Respiratory system
• Storage Class Code: 5.1B - Oxidizing hazardous materials
• WGK: WGK 3
• Flash Point(F): not determined
• Flash Point(C): not determined
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves