176176
Trifluoromethanesulfonic anhydride
99%
Synonym(s):
Triflic anhydride
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About This Item
Linear Formula:
(CF3SO2)2O
CAS Number:
Molecular Weight:
282.14
UNSPSC Code:
12352101
NACRES:
NA.22
PubChem Substance ID:
EC Number:
206-616-8
Beilstein/REAXYS Number:
1813600
MDL number:
Assay:
99%
Form:
liquid
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
InChI
1S/C2F6O5S2/c3-1(4,5)14(9,10)13-15(11,12)2(6,7)8
InChI key
WJKHJLXJJJATHN-UHFFFAOYSA-N
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
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.
Catalyst for glycosylation for synthesis of polysaccharides
Reagent for stereoselective synthesis of mannosazide methyl uronate donors
Activator for direct glycosylation with anomeric hydroxy sugars
Reagent for stereoselective synthesis of mannosazide methyl uronate donors
Activator for direct glycosylation with anomeric hydroxy sugars
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signalword
Danger
hcodes
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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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)
Controlled star poly (2-oxazoline) s: Synthesis, characterization
Laetitia P,et al.
European Polymer Journal, 122, 109323-109323 (2020)
The conversion of secondary amides to tetrazoles with trifluoromethanesulfonic anhydride and sodium azide
Thomas EW
Synthesis, 1993(08), 767-768 (1993)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 176176-250G | 04061838752789 |
| 176176-4KG | 04061833688458 |
| 176176-500G | 04061833544822 |
| 176176-10G | 04061838752765 |
| 176176-1KG | 04061838752772 |
| 176176-50G | 04061838752796 |
| 176176-5G | 04061838752802 |
| 176176-PZ | 04061823818766 |