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A10173 Trifluoromethanesulfonic acid, 98+%

CAS Number
1493-13-6
Synonyms
Triflic acid

Stock No. Size Price ($) Quantity Availability
A10173-09 10g 23.20
A10173-18 50g 75.20
A10173-30 250g 301.00
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Trifluoromethanesulfonic acid, 98+%

MDL
MFCD00007514
EINECS
216-087-5

Chemical Properties

Formula
CHF3O3S
Formula Weight
150.07
Melting point
-40°
Boiling Point
161-162°
Flash Point
None
Density
1.708
Refractive Index
1.3270
Storage & Sensitivity
Hygroscopic. Store under Nitrogen. Ambient temperatures.
Solubility
Miscible with water, dimethyl sulfoxide, dimethyl formamide and acetonitrile.

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.

Notes

Hygroscopic. Incompatible with strong oxidizing agents, strong bases, water and metals.

Literature References

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).

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).

For use in direct electrophilic amination of arenes, see Trimethyl­silyl­ 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).

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):

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.

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.

GHS Hazard and Precautionary Statements

Hazard Statements: H290-H302-H314-H335

May be corrosive to metals. Harmful if swallowed. Causes severe skin burns and eye damage. May cause respiratory irritation.

Precautionary Statements: P234-P260-P264b-P270-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P390-P501c

Keep only in original container. Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Rinse mouth. Do NOT induce vomiting. Wash contaminated clothing before reuse. Absorb spillage to prevent material damage. Dispose of contents/ container to an approved waste disposal plant

Other References

Merck
14,9676
Beilstein
1812100
Hazard Class
8
Packing Group
II
Harmonized Tariff Code
2904.99
TSCA
Yes
RTECS
PB2771000

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