Diethyl cyanomethylphosphonate

Base Information

• Chemical Name: Diethyl cyanomethylphosphonate
• CAS No.: 2537-48-6
• Molecular Formula: C6H12NO3P
• Molecular Weight: 177.14
• Hs Code.: 29310095
• European Community (EC) Number: 219-806-0
• NSC Number: 407826
• DSSTox Substance ID: DTXSID20180015
• Nikkaji Number: J149.878I
• Wikidata: Q72469243
• Mol file: 2537-48-6.mol

Synonyms:Cyanomethanephosphonicacid, diethyl ester (6CI);Phosphonic acid, (cyanomethyl)-, diethyl ester(7CI,8CI,9CI);(Cyanomethyl)phosphonicacid diethyl ester;(Diethoxyphosphinyl)acetonitrile;Diethyl (cyanomethyl)phosphonate;NSC 407826;O,O-Diethyl (cyanomethyl)phosphonate;

Chemical Property of Diethyl cyanomethylphosphonate

Chemical Property:

• Appearance/Colour: clear colorless to light yellow liquid
• Vapor Pressure: 0.000831mmHg at 25°C
• Refractive Index: n20/D 1.434(lit.)
• Boiling Point: 305.2 °C at 760 mmHg
• Flash Point: 117.3 °C
• PSA: 69.13000
• Density: 1.122 g/cm³
• LogP: 1.77608
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Soluble), Methanol (Slightly)
• Water Solubility.: Miscible with water, chloroform, terahydrofuran, ethyl acetate and methylene chloride.
• XLogP3: 0
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 177.05548024
• Heavy Atom Count: 11
• Complexity: 185

Purity/Quality:

≥98.0% ^*data from raw suppliers

Diethyl cyanomethylphosphonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn,C
• Hazard Codes: Xi,Xn,C
• Statements: 38-36/37/38-20/21/22-34-36/38
• Safety Statements: 26-28-36/37/39-23-45-27-36/37-9

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOP(=O)(CC#N)OCC
• Uses: Wittig reagent. 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.

Technology Process of Diethyl cyanomethylphosphonate

There total 9 articles about Diethyl cyanomethylphosphonate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

chloroacetonitrile (107-14-2) + triethyl phosphite (122-52-1) → diethyl 1-cyanomethylphosphonate (2537-48-6)

Guidance literature:

at 150 ℃; for 4h;

Reference yield: 95.0%

cyanomethyl bromide (590-17-0) + triethyl phosphite (122-52-1) → diethyl 1-cyanomethylphosphonate (2537-48-6)

Guidance literature:

for 0.0333333h; microwave irradiation;

DOI:10.1080/10426500008043680

Reference yield: 88.0%

diethyl chlorophosphate (814-49-3) + acetonitrile (75-05-8,26809-02-9) → diethyl 1-cyanomethylphosphonate (2537-48-6)

Guidance literature:

acetonitrile; With lithium hexamethyldisilazane; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

diethyl chlorophosphate; In tetrahydrofuran; at -78 - 0 ℃; for 0.25h;

With hydrogenchloride; In tetrahydrofuran; hexane; Further stages.;

DOI:10.1039/b003371p

upstream raw materials:

chloroacetonitrile

triethyl phosphite

diethyl chlorophosphate

acetonitrile

Downstream raw materials:

phosphonoacetic acid

1-Cyano-2-phenylethylphosphonsaeurediethylester

[3,5,5-Trimethyl-cyclohex-2-en-(E)-ylidene]-acetonitrile

7-hydroxy-3,7-dimethyloctanenitrile

Refernces

• 1、 Lorga, Bogdan,Ricard, Louis,Savignac, Philippe. "Carbanionic displacement reactions at phosphorus. Part III.1 Cyanomethylphosphonate vs. cyanomethylenediphosphonate. Synthesis and solid-state structures". . p. 3311 - 3316. Retrieved 2000.
• 2、 Wu, Ming-Yu,Esteban, Gerard,Brogi, Simone,Shionoya, Masahi,Wang, Li,Campiani, Giuseppe,Unzeta, Mercedes,Inokuchi, Tsutomu,Butini, Stefania,Marco-Contelles, Jose. "Donepezil-like multifunctional agents: Design, synthesis, molecular modeling and biological evaluation". . p. 864 - 879. Retrieved 2016/08/18.
• 3、 -. "Multi-target-oriented protective agent neurocyte". Paragraph 0118; 0119; 0120. . Retrieved 2017/03/28.