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158534

Sigma-Aldrich

Trifluoromethanesulfonic acid

reagent grade, 98%

Synonym(s):

TFMSA, Triflic acid

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About This Item

Linear Formula:
CF3SO3H
CAS Number:
Molecular Weight:
150.08
Beilstein:
1812100
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.21

grade

reagent grade

Quality Level

vapor density

5.2 (vs air)

vapor pressure

8 mmHg ( 25 °C)

Assay

98%

form

liquid

refractive index

n20/D 1.327 (lit.)

bp

162 °C (lit.)

density

1.696 g/mL at 25 °C (lit.)

SMILES string

OS(=O)(=O)C(F)(F)F

InChI

1S/CHF3O3S/c2-1(3,4)8(5,6)7/h(H,5,6,7)

InChI key

ITMCEJHCFYSIIV-UHFFFAOYSA-N

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General description

Trifluoromethanesulfonic acid is the strongest monoprotic organic acid. It has been synthesized by the oxidation of bis(trifluoromethylthio)mercury with aqueous hydrogen peroxide. It undergoes complete dissociation in basic solvents such as dimethyl sulfoxide, dimethylacetamide and dimethylformamide. Its dissociation in non-aqueous solvents has been studied by conductometry. On mixing trifluoromethanesulfonic acid with HNO3, it forms nitronium trifluoromethane sulfonate, which is an excellent nitrating reagent.

Application

Trifluoromethanesulfonic acid is a versatile reagent, employed as catalyst for the following studies:
  • Friedel-Crafts acylation of aromatic compounds with methyl benzoate.
  • Addition reaction of dialkyl disulfides to terminal alkynes.
  • Synthesis of a single cyclic tetrasiloxane containing propylammonium trifluoromethanesulfonate and methyl side-chain groups (Am-CyTS).
  • Preparation of starting reagents for the synthesis of fluorinated 2,5-substituted 1-ethyl-1H-benzimidazole derivatives.
  • Synthesis of aryl triflates, the lactonization of alkenoic acids, and the formation of E-alkenes.
Trifluoromethanesulfonic acid may be used as an initiator for the cationic polymerization of styrene, hexamethylcyclotrisiloxane and L,L-dilactide.
Deglycosylation agent

Pictograms

CorrosionExclamation mark

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Met. Corr. 1 - Skin Corr. 1B - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 1

Flash Point(F)

>332.1 °F - Pensky-Martens closed cup

Flash Point(C)

> 166.7 °C - Pensky-Martens closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Cationic polymerization of hexamethylcyclotrisiloxane by trifluoromethanesulfonic acid and its derivatives, 2. Reaction involving activated trifluoromethylsulfonates.
Toskas G, et al.
Macromolecular Chemistry and Physics, 196(9), 2715-2735 (1995)
M Arisawa et al.
Organic letters, 3(5), 763-764 (2001-03-22)
[reaction: see text]. Addition of dialkyl disulfides to terminal alkynes is catalyzed by a rhodium-phosphine complex and trifluoromethanesulfonic acid giving (Z)-bis(alkylthio)olefins stereoselectively.
Aromatic nitration with nitric acid and trifluoromethanesulfonic acid.
Coon CL, et al.
The Journal of Organic Chemistry, 38(25), 4243-4248 (1973)
Tetrahedron, 49, 7119-7119 (1993)
Determination of the rate constants of the elementary steps in the cationic polymerization of styrene by trifluoromethanesulfonic acid.
Kunitake T and Takarabe K.
Macromolecules, 12(6), 1061-1067 (1979)

Articles

Friedel-Crafts acylation with Lewis acid catalysts forms monoacylated products via electrophilic aromatic substitution of arenes.

Friedel-Crafts acylation with Lewis acid catalysts forms monoacylated products via electrophilic aromatic substitution of arenes.

Friedel-Crafts acylation with Lewis acid catalysts forms monoacylated products via electrophilic aromatic substitution of arenes.

Friedel-Crafts acylation with Lewis acid catalysts forms monoacylated products via electrophilic aromatic substitution of arenes.

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