Skip to Content
Merck
CN

158534

Trifluoromethanesulfonic acid

reagent grade, 98%, liquid

Synonym(s):

TFMSA, Triflic acid

Sign In to View Organizational & Contract Pricing

Select a Size

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:
12352100
PubChem Substance ID:
24849764
NACRES:
NA.21

Key Documents

View All Documentation
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

Product Name

Trifluoromethanesulfonic acid, reagent grade, 98%

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.)

pH

0.11

bp

162 °C (lit.)

solubility

water: soluble 1.600 g/L at 20 °C

density

1.696 g/mL at 25 °C (lit.)

functional group

fluoro
triflate

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

Deglycosylation agent
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.

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

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKCZ2923
MKCV8787
MKCW0675
MKCV6010
WXBF4735V

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

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

Visit the Document Library

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.
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
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)
View All Related Papers

Articles

Friedel–Crafts Acylation

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

傅-克酰基化反应

傅-克酰基化反应是一种芳烃与酰氯或酸酐使用强路易斯酸催化剂的反应。该反应通过亲电芳族取代进行，形成单酰化产物。

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