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A10218 Diethyl cyanomethylphosphonate, 98+%

Numéro de CAS
Cyanomethylphosphonic acid diethyl ester
Diethyl phosphonoacetonitrile

Stock No. Conditionnement Prix ($) Quantité Disponibilité
A10218-14 25g 85,70
A10218-22 100g 271,00
A10218-36 500g 1012,00
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Diethyl cyanomethylphosphonate, 98+%


Propriétés chimiques

Poids moleculaire
Point d'ébullition
Point d'éclair
Indice de réfraction
Storage & Sensitivity
Ambient temperatures.
Miscible with water, chloroform, terahydrofuran, ethyl acetate and methylene chloride.


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.


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

Références bibliographiques

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.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H302-H312-H315-H319-H332-H335

Harmful if swallowed. Harmful in contact with skin. Causes skin irritation. Causes serious eye irritation. Harmful if inhaled. May cause respiratory irritation.

Mentions de prudence: P261-P264b-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P312-P330-P332+P313-P337+P313-P362-P501c

Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Rinse mouth. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant

Autres références

Classe de danger
Groupe d'emballage
Code tarifaire harmonisé


Consulté récemment

Produits chimiques

Sciences de la vie

Métaux et matériaux


Analytique et matériel de laboratoire