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347817

Sigma-Aldrich

Trifluoromethanesulfonic acid

ReagentPlus®, ≥99%

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

vapor density

5.2 (vs air)

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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This Item
158534369632T6508
vibrant-m

347817

Trifluoromethanesulfonic acid

vibrant-m

158534

Trifluoromethanesulfonic acid

vibrant-m

369632

Trifluoromethanesulfonic acid-d

vibrant-m

T6508

Trifluoroacetic acid

assay

≥99%

assay

98%

assay

-

assay

99%

bp

162 °C (lit.)

bp

162 °C (lit.)

bp

162 °C (lit.)

bp

72.4 °C (lit.)

vapor density

5.2 (vs air)

vapor density

5.2 (vs air)

vapor density

-

vapor density

3.9 (vs air)

refractive index

n20/D 1.327 (lit.)

refractive index

n20/D 1.327 (lit.)

refractive index

-

refractive index

n20/D 1.3 (lit.)

vapor pressure

8 mmHg ( 25 °C)

vapor pressure

8 mmHg ( 25 °C)

vapor pressure

-

vapor pressure

97.5 mmHg ( 20 °C)

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

Product No.
Description
Pricing

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pictograms

CorrosionExclamation mark

signalword

Danger

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

8A - Combustible, corrosive hazardous materials

wgk_germany

WGK 1

flash_point_f

332.1 °F - Pensky-Martens closed cup

flash_point_c

> 166.7 °C - Pensky-Martens closed cup

ppe

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


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Customers Also Viewed

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)
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)
Electrochemical studies of sulfonates in non-aqueous solvents: Part III. Trifluoromethanesulfonic acid as a strong acid in dipolar aprotic solvents and acetic acid.
Fujinaga T and Sakamoto I.
J. Electroanal. Chem. Interfac. Electrochem., 85(1), 185-201 (1977)

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