Trifluoromethanesulfonic acid, 98+%, Thermo Scientific Chemicals
Trifluoromethanesulfonic acid, 98+%, Thermo Scientific Chemicals
Thermo Scientific Chemicals

Trifluoromethanesulfonic acid, 98+%, Thermo Scientific Chemicals

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Catalog number A10173.30
also known as A10173-30
Price (USD)/ Each
294.65
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327.00 
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Quantity:
250 g
Request bulk or custom format
Price (USD)/ Each
294.65
Online exclusive
327.00 
Save 32.35 (10%)
Add to cart
Trifluoromethanesulfonic acid, 98+%, Thermo Scientific Chemicals
Catalog numberA10173.30
Price (USD)/ Each
294.65
Online exclusive
327.00 
Save 32.35 (10%)
-
Add to cart
Chemical Identifiers
CAS1493-13-6
IUPAC Nametrifluoromethanesulfonic acid
Molecular FormulaCHF3O3S
InChI KeyITMCEJHCFYSIIV-UHFFFAOYSA-N
SMILESOS(=O)(=O)C(F)(F)F
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SpecificationsSpecification SheetSpecification Sheet
FormFuming liquid
CommentMay darken on storage
Assay (unspecified)≥98.0%
Appearance (Color)Clear colorless to yellow
Trifluoromethanesulfonic acid acts as a catalyst for esterification reactions and an acidic titrant in nonaqueous acid-base titration. It is useful in protonations due to the presence of conjugate base triflate is non nucleophilic. It serves as a deglycosylation agent for glycoproteins. In addition, it is a precursor and a catalyst in organic chemistry. It reacts with acyl halides to prepare mixed triflate anhydrides, which are strong acylating agents used in Friedel-Crafts reactions. It acts as a key starting material for the preparation of ethers and olefins by reacting with alcohols as well as to prepare trifluoromethanesulfonic anhydride by dehydration reaction.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications
Trifluoromethanesulfonic acid acts as a catalyst for esterification reactions and an acidic titrant in nonaqueous acid-base titration. It is useful in protonations due to the presence of conjugate base triflate is non nucleophilic. It serves as a deglycosylation agent for glycoproteins. In addition, it is a precursor and a catalyst in organic chemistry. It reacts with acyl halides to prepare mixed triflate anhydrides, which are strong acylating agents used in Friedel-Crafts reactions. It acts as a key starting material for the preparation of ethers and olefins by reacting with alcohols as well as to prepare trifluoromethanesulfonic anhydride by dehydration reaction.

Solubility
Miscible with water, dimethyl sulfoxide, dimethyl formamide and acetonitrile.

Notes
Hygroscopic. Incompatible with strong oxidizing agents, strong bases, water and metals.
RUO – Research Use Only

General References:

  1. One of the strongest available monoprotic acids. For a review of the chemistry of triflic acid and its derivatives, see: Chem. Rev., 77, 69 (1977).
  2. Simple triflic esters, readily prepared by reaction with alcohols, are powerful alkylating agents and must be handled with extreme care because of their irritating effect on the lungs. For a review, see: Synthesis, 85 (1982).
  3. For use in direct electrophilic amination of arenes, see Trimethyl silyl azide, L00173. Effects direct oxy-functionalization of aromatics in combination with bis(TMS) peroxide: J. Org. Chem., 54, 1204 (1989); or sodium perborate: Synlett, 39 (1991).
  4. Adds to both internal and terminal alkynes to give vinyl triflates: J. Am. Chem. Soc., 91, 4600 (1969); Org. Synth. Coll., 9, 472 (1998). Reaction in the presence of a nitrile provides a route to sterically hindered 2,4,6-trisubstituted pyrimidines: Synthesis, 881 (1990):
  5. Murashige, R.; Ohtsuka, Y.; Sagisawa, K.; Shiraishi, M. Versatile synthesis of 3, 4-dihydroisoquinolin-1 (2H)-one derivatives via intra-molecular Friedel-Crafts reaction with trifluoromethanesulfonic acid. Tetrahedron Lett. 2015, 56 (23), 3410-3412.
  6. Imai, S.; Kikui, H.; Moriyama, K.; Togo, H. One-pot preparation of 2, 5-disubstituted and 2, 4, 5-trisubstituted oxazoles from aromatic ketones with molecular iodine, oxone, and trifluoromethanesulfonic acid in nitriles. Tetrahedron 2015, 71 (33), 5267-5274.