Dietil cianometilfosfonato, 96 %, Thermo Scientific Chemicals

Name: Dietil cianometilfosfonato, 96 %, Thermo Scientific Chemicals
SKU: A10218.14

CAS: 2537-48-6 | C6H12NO3P | 177.14 g/mol

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25 g

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Número de catálogo A10218.14

también denominado A10218-14

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25 g

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Identificadores químicos

CAS2537-48-6

IUPAC Namediethyl (cyanomethyl)phosphonate

Molecular FormulaC6H12NO3P

InChI KeyKWMBADTWRIGGGG-UHFFFAOYSA-N

SMILESCCOP(=O)(CC#N)OCC

Especificaciones Specification Sheet

Hoja de especificaciones

Appearance (Color)Clear colorless to pale yellow

FormLiquid

Assay (GC)≥95.0%

Refractive Index1.4290-1.4350 @ 20?C

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.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Aplicaciones
El fosfonato cianometilo dietílico se utiliza como intermedio en la reacción de Horner-Emmons para la síntesis de nitrilos sustituidos y sus derivados de amida y heterocíclicos. Se considera un reactivo de Wittig modificado que se utiliza en la preparación de nitrilos alfa, beta-insaturados de cetonas o aldehídos como el 3-hidroxi-3-metilbutanol. Reacciona con epóxidos y nitronas para preparar ciclopropanos y aziridinas sustituidas por cianuro respectivamente. Participa activamente en la síntesis de alcanonitrilos alfa-arilados a través de la reacción con yoduros de arilo en presencia de CuI.

Solubilidad
Miscible con agua, cloroformo, terahidrofurano, acetato de etilo y cloruro de metileno.

Notas
Incompatible con ácidos, bases, agentes oxidantes y agentes reductores.

RUO – Research Use Only

General References:

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.