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2537-48-6 - Diethyl cyanomethylphosphonate, 98+% - Cyanomethylphosphonic acid diethyl ester - Diethyl phosphonoacetonitrile - A10218 - Alfa Aesar

A10218 Diethyl cyanomethylphosphonate, 98+%

Número CAS
2537-48-6
Nombre Alternativo
Cyanomethylphosphonic acid diethyl ester
Diethyl phosphonoacetonitrile

Tamaño Precio ($) Cantidad Disponibilidad
25g 81,90
100g 260,00
500g 982,00
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Diethyl cyanomethylphosphonate, 98+%

MDL
MFCD00001893
EINECS
219-806-0

Propiedades químicas

Fórmula
C6H12NO3P
Peso molecular
177.14
Punto de ebullición
132-135°/1.2mm
Punto de inflamabilidad
>110°(230°F)
Densidad
1.094
Índice de refracción
1.4330
Solubilidad
Miscible with water, chloroform, terahydrofuran, ethyl acetate and methylene chloride.

Aplicaciones

Diethyl cyanomethyl phosphonate is used as an intermediate in Horner-Emmons reaction for the synthesis of substituted nitriles and their amide and heterocyclic derivatives. It is known as a modified Wittig reagent used in the preparation of alpha, beta-unsaturated nitriles from ketones or aldehydes like 3-hydroxy-3-methylbutanal. It reacts with epoxides and nitrones to prepare cyano-substituted cyclopropanes and aziridines respectively. It is actively involved in the synthesis of alpha-arylated alkanenitriles via reaction with aryl iodides in presence of CuI.

Notas

Incompatible with acids, bases, oxidizing agents and reducing agents.

Referencias documentales

Horner-Wadsworth-Emmons olefination converts carbonyl compounds to substituted acrylonitriles: J. Am. Chem. Soc., 83, 1733 (1961); J. Org. Chem., 30, 505 (1965). LiOH has been found to be an effective base for this reaction: Tetrahedron Lett., 44, 1333 (2003). See Appendix 1. See also 3-Coumaranone, A10202.

The active methylene group can be monoalkylated under phase transfer conditions with alkyl iodides or allylic or benzylic bromides: Synthesis, 516 (1975). Use of alumina as base leads predominantly to the Knoevenagel product rather than the Wadsworth-Emmons: Tetrahedron, 41, 1259 (1985).

Grun, A.; Balint, E.; Keglevich, G. Solid-Liquid Phase C-Alkylation of Active Methylene Containing Compounds under Microwave Conditions. Catalysts 2015, 5 (2), 634-652.

Dai, Y.; Yu, B. Total synthesis of astrosterioside A, an anti-inflammatory asterosaponin. Chem. Commun. 2015, 51 (72), 13826-13829.

Indicaciones de peligro y de precaución del GHS

Indicaciones de peligro (UE): H331-H302-H312-H315-H319

Toxic if inhaled. Harmful if swallowed. Harmful in contact with skin. Causes skin irritation. Causes serious eye irritation.

Indicaciones de precaución: P261-P280-P305+P351+P338-P304+P340-P311-P362-P301+P312-P312-P405-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/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. Call a POISON CENTER or doctor/physician. Take off contaminated clothing and wash before reuse. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Otras referencias

Beilstein
1772981
Clase de peligro
6.1
Grupo de embalaje
III
Código de tarifa arancelaria unificado
2931.90
TSCA
No

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