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358-23-6 - Trifluoromethanesulfonic anhydride, 98% - Triflic anhydride - A11767 - Alfa Aesar

A11767 Trifluoromethanesulfonic anhydride, 98%

Número CAS
358-23-6
Nombre Alternativo
Triflic anhydride

Tamaño Precio ($) Cantidad Disponibilidad
10g 49,75
25g 98,47
50g 155,70
100g 290,70
250g 400,82
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Trifluoromethanesulfonic anhydride, 98%

MDL
MFCD00000408
EINECS
206-616-8

Propiedades químicas

Fórmula
C2F6O5S2
Peso molecular
282.13
Punto de fusión
-80°
Punto de ebullición
81-83°
Densidad
1.720
Índice de refracción
1.3210
Sensibilidad
Moisture Sensitive
Solubilidad
Miscible with dichloromethane. Immiscible with hydrocarbons.

Aplicaciones

Trifluoromethanesulfonic anhydride is used to convert phenols and imine into triflic ester and NTf group. It is a strong electrophile used for the introduction of triflyl group in chemical synthesis. It serves as a reagent in the preparation of alkyl and vinyl triflates, and for the stereoselective synthesis of mannosazide methyl uronate donors. It acts as a catalyst for glycosylation with anomeric hydroxy sugars to prepare polysaccharides.

Notas

Moisture sensitive. Incompatible with water, strong bases, strong oxidizing agents, acids and alcohols.

Referencias documentales

For examples of preparation of alkyl and aryl triflates, and use of the latter in the Stille coupling reaction, see: Org. Synth. Coll., 6, 324 (1988); 9, 553 (1998). Alkyl triflates undergo solvolysis reactions between five and seven powers of ten times more rapidly than the corresponding halides or tosylates: J. Am. Chem. Soc., 97, 6478 (1975); Angew. Chem. Int. Ed., 9, 521 (1970). For a review of the chemistry of triflate esters, see: Synthesis, 85 (1982).

Enolizable carbonyl compounds in the presence of base can be converted to vinyl (enol) triflates: Synthesis, 85 (1982); Org. Synth. Coll., 6, 757 (1988). For conditions employing preferred base, 2,6-Di-tert-butyl-4-methyl­pyridine, L14143, see: Org. Synth. Coll., 8, 97, 126 (1993). Enol triflates behave as a source of vinyl cations. For reviews, see: Angew. Chem. Int. Ed., 17, 333 (1978); Acc. Chem. Res., 11, 107 (1978); 15, 348 (1982); 21, 147 (1988).

For formation of keteniminium triflates, see N,N-Dimethyl­acetamide, A10924.

The Ritter reaction is normally most successful with tertiary alcohols. In contrast, a useful variation allows conversion of primary or secondary alcohols to amides in good yield: Tetrahedron Lett., 30, 581 (1989):

For use in the Vilsmeier formylation of less active substrates, see N,N-Dimethyl­formamide, A13547.

Triflic anhydride has also been found to promote the nitration of arenes, even deactivated ones, under mild conditions: Synthesis, 1087 (1992).

For a review of chemical transformations induced by the reagent, see: Tetrahedron, 56, 3077 (2000). For a brief feature on uses in synthesis, see: Synlett, 390 (2004).

Dadgar, M.; Kalkhorani, N. M. Efficient and practical one-pot route to synthesise quinazolin4 (3H)-ones using trifluoromethanesulfonic anhydride and 2-chloropyridine. J. Chem. Res. 2015, 39 (2), 120-122.

Huang, P. Q.; Lang, Q. W.; Wang, A. E.; Zheng, J. F. Direct reductive coupling of secondary amides: chemoselective formation of vicinal diamines and vicinal amino alcohols. Chem. Commun. 2015, 51 (6), 1096-1099.

Indicaciones de peligro y de precaución del GHS

Indicaciones de peligro (UE): H314-H318

Causes severe skin burns and eye damage. Causes serious eye damage.

Indicaciones de precaución: P260-P280-P303+P361+P353-P305+P351+P338-P301+P330+P331-P304+P340-P310-P363-P405-P501a

Do not breathe dust/fume/gas/mist/vapours/spray. 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 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. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Immediately call a POISON CENTER or doctor/physician. Wash contaminated clothing before reuse. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Otras referencias

Beilstein
1813600
Clase de peligro
8
Grupo de embalaje
II
Código de tarifa arancelaria unificado
2904.90
TSCA
Yes
RTECS
PB2772000

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