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Sigma-Aldrich

Trifluoromethanesulfonic acid

ReagentPlus®, ≥99%

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Synonym(s):
Triflic acid
Linear Formula:
CF3SO3H
CAS Number:
Molecular Weight:
150.08
Beilstein:
1812100
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

vapor density

5.2 (vs air)

Quality Level

vapor pressure

8 mmHg ( 25 °C)

product line

ReagentPlus®

Assay

≥99%

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 a strong organic acid. It can be prepared by reacting bis(trifluoromethylthio)mercury with H2O2. On mixing with HNO3, it affords a nitrating reagent (a nitronium salt). This reagent is useful for the nitration of aromatic compounds. Its dissociation in various organic solvents has been studied.

Application

Trifluoromethanesulfonic acid can be used as a catalyst to prepare:
  • Substituted tetrahydrofurans and tetrahydropyrans by cyclization of corresponding unsaturated alcohols under acidic conditions.
  • Nitriles from corresponding aldehydes by Schmidt reaction.
  • Disubstituted five-membered ring lactones by allylboration reaction between 2-alkoxycarbonyl allylboronates and aldehydes.

It can also be used as a catalyst in the Fischer glycosylation and Friedel-Crafts acylation reactions.
Deglycosylation agent

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

accessory

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Description
Pricing

related product

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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Chemoselective Schmidt reaction mediated by triflic acid: selective synthesis of nitriles from aldehydes
Rokade BV and Prabhu KR
The Journal of Organic Chemistry, 77(12), 5364-5370 (2012)
Use of trifluoromethanesulfonic acid in fischer glycosylations.
Wessel HP.
Journal of Carbohydrate Chemistry, 7(1), 263-269 (1988)
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)
Trifluoromethanesulfonic acid and derivatives.
Howells RD and Cown JDM.
Chemical Reviews, 77(1), 69-92 (1977)

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