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Merck
모든 사진(1)

문서

91737

Sigma-Aldrich

Trifluoromethanesulfonic anhydride

purum, ≥98.0% (T)

동의어(들):

Tf2O, 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 코드:
12352101
PubChem Substance ID:
NACRES:
NA.22

vapor density

5.2 (vs air)

Quality Level

vapor pressure

8 mmHg ( 20 °C)

grade

purum

분석

≥98.0% (T)

형태

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

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애플리케이션

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.

기타 정보

Electrophilic trifyl source. Reviews

픽토그램

Flame over circleCorrosionExclamation mark

신호어

Danger

유해 및 위험 성명서

Hazard Classifications

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

표적 기관

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

개인 보호 장비

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


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문서 라이브러리 방문

I. Baraznenok et al.
Tetrahedron, 56, 3077-3077 (2000)
Tf2O as a rapid and efficient promoter for the dehydrative Friedel?Crafts acylation of aromatic compounds with carboxylic acids.
Khodaei MM, et al.
Tetrahedron Letters, 48(24), 4199-4202 (2007)
Synthesis, 85-85 (1982)
Synthesis of pyrimidines by direct condensation of amides and nitriles.
Movassaghi M & Hill MD.
Nature Protocols, 2(8), 2018-2018 (2007)
Mild and efficient deoxygenation of sulfoxides to sulfides with triflic anhydride/potassium iodide reagent system.
Bahrami K, et al.
Synthesis, 2008(16), 2543-2546 (2008)

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