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81927-55-1 - Benzyl 2,2,2-trichloroacetimidate, 98% - 2,2,2-Trichloroacetimidic acid benzyl ester - A12387 - Alfa Aesar

A12387 Benzyl 2,2,2-trichloroacetimidate, 98%

Número CAS
81927-55-1
Nombre Alternativo
2,2,2-Trichloroacetimidic acid benzyl ester

Tamaño Precio ($) Cantidad Disponibilidad
5g 27,30
25g 88,00
50g 164,00
250g 684,00
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Benzyl 2,2,2-trichloroacetimidate, 98%

MDL
MFCD00000805
EINECS
617-271-1

Propiedades químicas

Fórmula
C9H8Cl3NO
Peso molecular
252.53
Punto de ebullición
110-114°/0.5mm
Punto de inflamabilidad
>110°(230°F)
Densidad
1.356
Índice de refracción
1.5450
Sensibilidad
Moisture Sensitive
Solubilidad
Miscible with cyclohexane/dichloromethane.

Aplicaciones

Benzyl 2,2,2-trichloroacetimidate is used for the acid-catalyzed benzylation of hydroxy groups. It acts as reagent during the synthesis of funiculosin dimethyl ether and (S)-3-(benzyloxy)-2-methylpropanal. It can also be used for mild esterification of carboxylic acids in the presence of a catalytic amount of BF3 etherate.

Notas

Moisture and light sensitive. Incompatible with strong oxidizing agents and strong acids.

Referencias documentales

Mild, selective benzylating agent. Formation of benzyl ethers from alcohols at room temperature is catalyzed by triflic acid; isopropylidene and benzylidene protecting groups are unaffected: J. Chem. Soc., Perkin 1., 2247 (1985). TMS triflate has also been recommended as a catalyst, avoiding racemization of sensitive substrates: Tetrahedron, 43, 1619 (1993). For use in the preparation of benzyl ethers of ß-hydroxy esters, see: Synthesis, 568 (1987).

The reagent can also be used for mild esterification of carboxylic acids in the presence of a catalytic amount of BF3 etherate: Synthesis, 168 (1997). For conversion of N-Boc groups to N-Cbz, catalyzed by triflic acid, see: J. Org. Chem., 55, 5170 (1990). See also Appendix 6.

Chen, T.; Altmann, K. H. Directed Hydrogenations and an Ireland-Claisen Rearrangement Linked to Evans-Tishchenko Chemistry: The Highly Efficient Total Synthesis of the Marine Cyclodepsipeptide Doliculide. Chem. Eur. J 2015, 21 (23), 8403-8407.

Miller, D. C.; Carbain, B.; Beale, G. S.; Alhasan, S. F.; Reeves, H. L.; Baisch, U.; Newell, D. R.; Golding, B. T.; Griffin, R. J. Regioselective sulfamoylation at low temperature enables concise syntheses of putative small molecule inhibitors of sulfatases. Org. Biomol. Chem. 2015, 13 (18), 5279-5284 .

Indicaciones de peligro y de precaución del GHS

Indicaciones de peligro (UE): H302-H315-H319-H335

Harmful if swallowed. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Indicaciones de precaución: P261-P280a-P305+P351+P338-P304+P340-P405-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Otras referencias

Beilstein
2525375
Código de tarifa arancelaria unificado
2925.29
TSCA
No

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