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347817

Sigma-Aldrich

Trifluoromethanesulfonic acid

ReagentPlus®, ≥99%

Synonym(s):

Triflic acid

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About This Item

Linear Formula:
CF3SO3H
CAS Number:
1493-13-6
Molecular Weight:
150.08
Beilstein:
1812100
EC Number:
216-087-5
MDL number:
MFCD00007514
UNSPSC Code:
12352106
PubChem Substance ID:
24861529
NACRES:
NA.22

vapor density

5.2 (vs air)

Quality Level

200

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

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Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H290,H302,H314,H335

Hazard Classifications

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

Target Organs

Respiratory system

WGK

WGK 1

Flash Point(F)

Pensky-Martens closed cup

Flash Point(C)

Pensky-Martens closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Triflic acid-catalysed cyclisation of unsaturated alcohols
Coulombel L and Dunach E
Green Chemistry, 6(10), 499-501 (2004)
Triflic acid-catalyzed additions of 2-alkoxycarbonyl allylboronates to aldehydes. Study of scope and mechanistic investigation of the reaction stereochemistry
Elford TG, et al.
The Journal of Organic Chemistry, 72(4), 1276-1284 (2007)
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.
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