Skip to Content
MilliporeSigma
All Photos(1)

Documents

158534

Sigma-Aldrich

Trifluoromethanesulfonic acid

reagent grade, 98%

Synonym(s):

TFMSA, Triflic acid

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Linear Formula:
CF3SO3H
CAS Number:
1493-13-6
Molecular Weight:
150.08
Beilstein/REAXYS Number:
1812100
EC Number:
216-087-5
MDL number:
MFCD00007514
UNSPSC Code:
12352100
PubChem Substance ID:
24849764
NACRES:
NA.21

grade

reagent grade

Quality Level

200

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

Looking for similar products? Visit Product Comparison Guide

Related Categories

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

accessory

Product No.
Description
Pricing

pictograms

CorrosionExclamation mark
GHS05,GHS07

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Sorry, we don't have COAs for this product available online at this time.

If you need assistance, please contact Customer Support.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 5

1 of 5

Camatril™ Velours nitrile flock lined gloves size L

Z677450

Camatril™ Velours nitrile flock lined gloves

1,1,1-Trifluoroacetone 97%

Sigma-Aldrich

T62804

1,1,1-Trifluoroacetone

Trifluoromethanesulfonyl chloride ≥99%

Sigma-Aldrich

164798

Trifluoromethanesulfonyl chloride

Acetic acid SAJ first grade, ≥99.0%

Sigma-Aldrich

01-0290

Acetic acid

4,4′-Bis(chloromethyl)-1,1′-biphenyl 95%

Sigma-Aldrich

448753

4,4′-Bis(chloromethyl)-1,1′-biphenyl

Tetrahedron, 49, 5351-5351 (1993)
Polylactones, 8. Mechanism of the cationic polymerization of L, L-dilactide.
Kricheldorf HR and Dunsing R.
Macromolecular Chemistry and Physics, 187(7), 1611-1625 (1986)
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)
Shota Kinoshita et al.
Journal of the American Chemical Society, 137(15), 5061-5065 (2015-04-01)
In this study, a single cyclic tetrasiloxane containing propylammonium trifluoromethanesulfonate and methyl side-chain groups (Am-CyTS) was selectively prepared by the hydrolytic condensation of 3-aminopropyldiethoxymethylsilane using aqueous superacid trifluoromethanesulfonic acid. The (1)H NMR spectrum of Am-CyTS in D2O exhibited a single
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)
View All Related Papers

Articles

Friedel–Crafts Acylation

The Friedel–Crafts acylation is the reaction of an arene with acyl chlorides or anhydrides using a strong Lewis acid catalyst. This reaction proceeds via electrophilic aromatic substitution to form monoacylated products.

Protocols

Protocols for the Fmoc SPPS of Cysteine-containing Peptides

Overcome challenges in synthesis and disulfide bond formation with protocols for Fmoc solid-phase peptide synthesis of peptides with cysteine and methionine.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service