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347817 Sigma-Aldrich

Trifluoromethanesulfonic acid

ReagentPlus®, ≥99%

Synonym: Triflic acid

  • CAS Number 1493-13-6

  • Linear Formula CF3SO3H

  • Molecular Weight 150.08

  •  Beilstein/REAXYS Number 1812100

  •  EC Number 216-087-5

  •  MDL number MFCD00007514

  •  PubChem Substance ID 24861529

  •  NACRES NA.22

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Properties

Related Categories Acids, Acids & Bases, Chemical Synthesis, Organic Acids, Synthetic Reagents More...
vapor density   5.2 (vs air)
vapor pressure   8 mmHg ( 25 °C)
product line   ReagentPlus®
assay   ≥99%
refractive index   n20/D 1.327 (lit.)
bp   162 °C (lit.)
density   1.696 g/mL at 25 °C (lit.)
storage temp.   room temp
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

Packaging

100, 500 g in glass bottle

5, 25 g in ampule

Legal Information

ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Target organs 
Respiratory system
RIDADR 
UN 3265 8 / PGII
WGK Germany 
WGK 1
Flash Point(F) 
332.1 °F - Pensky-Martens closed cup
Flash Point(C) 
> 166.7 °C - Pensky-Martens closed cup

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

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Peer-Reviewed Papers
15

References

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