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

A10173 Trifluoromethanesulfonic acid, 98+%

Número CAS
1493-13-6
Nombre Alternativo
Triflic acid

Tamaño Precio ($) Cantidad Disponibilidad
10g 21,50
50g 71,90
250g 301,00
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Trifluoromethanesulfonic acid, 98+%

MDL
MFCD00007514
EINECS
216-087-5

Propiedades químicas

Fórmula
CHF3O3S
Peso molecular
150.07
Punto de fusión
-40°
Punto de ebullición
161-162°
Punto de inflamabilidad
None
Densidad
1.708
Índice de refracción
1.3270
Sensibilidad
Hygroscopic
Solubilidad
Miscible with water, dimethyl sulfoxide, dimethyl formamide and acetonitrile.

Aplicaciones

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.

Notas

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

Referencias documentales

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.

Indicaciones de peligro y de precaución del GHS

Indicaciones de peligro (UE): H302-H314-H318-H335

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

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

Do not breathe dusts or mists. 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.

Otras referencias

Merck
14,9676
Beilstein
1812100
Clase de peligro
8
Grupo de embalaje
II
Código de tarifa arancelaria unificado
2904.99
TSCA
Yes
RTECS
PB2771000

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