347817

Trifluoromethanesulfonic acid

ReagentPlus^®, ≥99%

• Synonym(s): 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: 12352106
• PubChem Substance ID: 24861529
• NACRES: NA.22

Properties

• 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.)
• 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

Description

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

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