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158534 Sigma-Aldrich

Trifluoromethanesulfonic acid

reagent grade, 98%

Synonym: TFMSA, 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 24849764

  •  NACRES NA.21

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Properties

Related Categories Acids, Acids & Bases, Chemical Synthesis, Organic Acids, Synthetic Reagents More...
Quality Level   200
grade   reagent grade
vapor density   5.2 (vs air)
vapor pressure   8 mmHg ( 25 °C)
assay   98%
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 HNO3, 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

Packaging

10, 50, 100 g in ampule

Safety & Documentation

Safety Information

Signal word 
Danger-Danger
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

Articles

Friedel–Crafts Acylation

The Friedel–Crafts acylation is the reaction of an arene with acyl chlorides or anhydrides using a strong Lewis acid catalyst. This reaction proceeds via electrophilic aromatic substitution to form m...
Keywords: Acylations, Catalysis, Electrophilic aromatic substitution, Microwave synthesis, Substitutions

Protocols

Fmoc SPPS Protocols for Cysteine Peptides

Peptides containing Cys can exist in either reduced (sulfhydryl) or oxidized inter/intra chain disulfide bonded forms. The synthesis of peptides containing Cys, therefore, presents special challenges...
Keywords: Alkylations, Asymmetric synthesis, Buffers, Centrifugation, Coupling reactions, Cyclizations, Eliminations, Evaporation, Filtration, High performance liquid chromatography, Hormones, Iodinations, Oxidations, Peptide synthesis, Purification, Racemizations, Rearrangements, Reductions, Solid phase peptide synthesis, Solvents, Thiolysis

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The molarity calculator tool provides lab-ready directions describing how to prepare an acid or base solution of specified Molarity (M) or Normality (N) from a concentrated acid or base solution. To ...

Peer-Reviewed Papers
15

References

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