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Merck

158534

Trifluoromethanesulfonic acid

reagent grade, 98%, liquid

Synonym(s):

TFMSA, Triflic acid

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About This Item

Linear Formula:
CF3SO3H
CAS Number:
1493-13-6
Molecular Weight:
150.08
NACRES:
NA.21
PubChem Substance ID:
24849764
UNSPSC Code:
12352100
EC Number:
216-087-5
MDL number:
MFCD00007514
Beilstein/REAXYS Number:
1812100
Assay:
98%
Form:
liquid
Grade:
reagent grade

Key Documents

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Product Name

Trifluoromethanesulfonic acid, reagent grade, 98%

InChI key

ITMCEJHCFYSIIV-UHFFFAOYSA-N

InChI

1S/CHF3O3S/c2-1(3,4)8(5,6)7/h(H,5,6,7)

SMILES string

OS(=O)(=O)C(F)(F)F

grade

reagent grade

vapor density

5.2 (vs air)

vapor pressure

8 mmHg ( 25 °C)

assay

98%

form

liquid

refractive index

n20/D 1.327 (lit.)

Quality Level

200

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

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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

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

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKDB2762
MKDB1363
MKDB2972
WXBF8064V
MKCZ2923

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Tetrahedron, 49, 5351-5351 (1993)
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)
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)
Aromatic nitration with nitric acid and trifluoromethanesulfonic acid.
Coon CL, et al.
The Journal of Organic Chemistry, 38(25), 4243-4248 (1973)
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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