176176

Trifluoromethanesulfonic anhydride

99%

• Synonym(s): 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: 24850557
• NACRES: NA.22

Properties

• vapor density: 5.2 (vs air)
• Quality Level: 200
• vapor pressure: 8 mmHg ( 20 °C)
• Assay: 99%
• 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

General description

Trifluoromethanesulfonic anhydride, also known as triflic anhydride, is an electrophilic reagent that is an efficient source of trifluoromethyl. It is commonly used in organic chemistry to convert oxygen-containing compounds to triflates and for the electrophilic activation and subsequent conversion of amides, sulfoxides, and phosphorus oxides.

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 as :

• A Reactant in the synthesis of Dipentaerythritol hexatriflate via triflatation method and Azido-diphenyl-acetic acid.
• Catalyst for glycosylation for synthesis of polysaccharides.
• Reagent for stereoselective synthesis of mannosazide methyl uronate donors.
• Activator for direct glycosylation with anomeric hydroxy sugars
• A methylation reagent to synthesize trifluoromethylated compounds by direct introduction of CF₃ group to (hetero)arenes.
• A reagent to prepare substituted tetrazoles from secondary amides using sodium azide.
• A reagent in Bischler−Napieraiski cyclization reaction along with 4-(N,N-dimethylamnino)pyridine.

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