347817

Trifluoromethanesulfonic acid

ReagentPlus^®, ≥99%

• Synonym(s): Triflic acid
• Linear Formula: CF₃SO₃H
• CAS Number: 1493-13-6
• Molecular Weight: 150.08
• Beilstein: 1812100
• EC Number: 216-087-5
• MDL number: MFCD00007514
• UNSPSC Code: 12352106
• PubChem Substance ID: 24861529
• NACRES: NA.22

Properties

• grade: reagent grade
• Quality Level: 200
• 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.)
• mp: - 40 °C
• solubility: 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

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

Deglycosylation agent

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.

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

Safety Information

• Pictograms: GHS05,GHS07
• Signal Word: Danger
• Hazard Statements: H290,H302,H314,H335
• Precautionary Statements: 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 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