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Merck
CN

176176

Trifluoromethanesulfonic anhydride

99%

Synonym(s):

Triflic anhydride

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About This Item

Linear Formula:
(CF3SO2)2O
CAS Number:
358-23-6
Molecular Weight:
282.14
UNSPSC Code:
12352101
NACRES:
NA.22
PubChem Substance ID:
24850557
EC Number:
206-616-8
Beilstein/REAXYS Number:
1813600
MDL number:
MFCD00000408

Key Documents

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Product Name

Trifluoromethanesulfonic anhydride, 99%

InChI key

WJKHJLXJJJATHN-UHFFFAOYSA-N

InChI

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

SMILES string

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

vapor density

5.2 (vs air)

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

Quality Level

200

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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 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.

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.

signalword

Danger

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

5.1B - Oxidizing hazardous materials

wgk

WGK 3

flash_point_f

not determinedboils before flash

flash_point_c

not determinedboils before flash

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
0000519959
0000519960
0000519958
0000514107
0000514107

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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)
Controlled star poly (2-oxazoline) s: Synthesis, characterization
Laetitia P,et al.
European Polymer Journal, 122, 109323-109323 (2020)
[11 C] phenytoin revisited: synthesis by [11 C] CO carbonylation and first evaluation as a P-gp tracer in rats
Joost V,et al.
EJNMMI Research, 2, 1-11 (2012)
Recent applications of trifluoromethanesulfonic anhydride in organic synthesis
Qixue Q, et al.
Angewandte Chemie (International Edition in English), 135, e202215008-e202215008 (2023)
Trifluoromethanesulfonic anhydride-4-(N, N-dimethylamino) pyridine as a reagent combination for effecting Bischler-Napieraiski cyclisation under mild conditions: application to total syntheses of the Amaryllidaceae alkaloids N-methylcrinasiadine, anhydrolycorinone, hippadine and oxoassoanine
David CR, et al.
Journal of the Chemical Society. Chemical Communications, 1993(24), 2551-2553 (1995)
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