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Sigma-Aldrich

Trifluoromethanesulfonic anhydride

99%

Synonym(s):

Triflic anhydride

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About This Item

Linear Formula:
(CF3SO2)2O
CAS Number:
Molecular Weight:
282.14
Beilstein:
1813600
EC Number:
MDL number:
UNSPSC Code:
12352101
PubChem Substance ID:
NACRES:
NA.22

Pricing and availability is not currently available.

vapor density

5.2 (vs air)

Quality Level

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.)

functional group

fluoro
triflate

SMILES string

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

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1 of 4

This Item
W310107240370W310162
grade

analytical standard

grade

FG, Halal, Kosher

grade

-

grade

FG, Fragrance grade, Halal, Kosher, natural

format

neat

format

-

format

-

format

-

application(s)

cleaning products
cosmetics
flavors and fragrances
food and beverages
personal care

application(s)

flavors and fragrances

application(s)

-

application(s)

flavors and fragrances

vapor density

3.5 (vs air)

vapor density

3.5 (vs air)

vapor density

3.5 (vs air)

vapor density

3.5 (vs air)

vapor pressure

0.15 mmHg ( 20 °C)

vapor pressure

0.15 mmHg ( 20 °C)

vapor pressure

0.15 mmHg ( 20 °C)

vapor pressure

0.15 mmHg ( 20 °C)

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. [1]

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.[2]
  • 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.[3]
  • A reagent to prepare substituted tetrazoles from secondary amides using sodium azide.[4]
  • A reagent in Bischler−Napieraiski cyclization reaction along with 4-(N,N-dimethylamnino)pyridine.[5]

Signal Word

Danger

Hazard Statements

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 determinedboils before flash

Flash Point(C)

not determinedboils before flash

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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    The conversion of secondary amides to tetrazoles with trifluoromethanesulfonic anhydride and sodium azide
    Thomas EW
    Synthesis, 1993(08), 767-768 (1993)
    Chimica Oggi, 22, 48-48 (2004)
    Trifluoromethanesulfonic Anhydride as a Low-Cost and Versatile Trifluoromethylation Reagent
    Ouyang Y, et al.
    Angewandte Chemie (International Edition in English), 57(23), 6926-6929 (2018)
    Synthesis, 735-735 (1993)
    Aldrichimica Acta, 16, 15-15 (1983)

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