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

A10218 Diethyl cyanomethylphosphonate, 98+%

CAS Number
2537-48-6
Synonyms
Cyanomethylphosphonic acid diethyl ester
Diethyl phosphonoacetonitrile

Size Price ($) Quantity Availability
25g 82.71
100g 262.65
500g 991.89
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Diethyl cyanomethylphosphonate, 98+%

MDL
MFCD00001893
EINECS
219-806-0

Chemical Properties

Formula
C6H12NO3P
Formula Weight
177.14
Boiling Point
132-135°/1.2mm
Flash Point
>110°(230°F)
Density
1.094
Refractive Index
1.4330
Solubility
Miscible with water, chloroform, terahydrofuran, ethyl acetate and methylene chloride.

Applications

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.

Notes

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

Literature 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.

GHS Hazard and Precautionary Statements

Hazard Statements: H331-H302-H312-H315-H319

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

Precautionary Statements: 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.

Other References

Beilstein
1772981
Hazard Class
6.1
Packing Group
III
Harmonized Tariff Code
2931.90
TSCA
No

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