158534

Trifluoromethanesulfonic acid

reagent grade, 98%

• Synonym(s): TFMSA, Triflic acid
• 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

Properties

• 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

Description

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 HNO_3, 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

Safety Information

• pictograms: GHS05,GHS07
• signalword: Danger
• hcodes: H290,H302,H314,H335
• pcodes: P234 - P261 - P280 - P301 + P312 - P303 + P361 + P353 - P305 + P351 + P338
• 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