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1493-13-6 - Trifluoromethanesulfonic acid, 98+% - Triflic acid - A10173 - Alfa Aesar

A10173 Trifluoromethanesulfonic acid, 98+%

Numéro de CAS
1493-13-6
Synonymes
Triflic acid

Conditionnement Prix ($) Quantité Disponibilité
10g 21,50
50g 71,90
250g 301,00
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Trifluoromethanesulfonic acid, 98+%

MDL
MFCD00007514
EINECS
216-087-5

Propriétés chimiques

Formule
CHF3O3S
Poids moleculaire
150.07
Point de fusion
-40°
Point d'ébullition
161-162°
Point d'éclair
None
Densité
1.708
Indice de réfraction
1.3270
Sensibilité
Hygroscopic
Solubilité
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.

Références bibliographiques

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.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H302-H314-H318-H335

Harmful if swallowed. Causes severe skin burns and eye damage. Causes serious eye damage. May cause respiratory irritation.

Mentions de prudence: P260u-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501a

IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Autres références

Merck
14,9676
Beilstein
1812100
Classe de danger
8
Groupe d'emballage
II
Code tarifaire harmonisé
2904.99
TSCA
Yes
RTECS
PB2771000

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