Diethyl (1-cyanoethyl)phosphonate

Base Information

• Chemical Name: Diethyl (1-cyanoethyl)phosphonate
• CAS No.: 29668-61-9
• Molecular Formula: C7H14 N O3 P
• Molecular Weight: 191.167
• Hs Code.: 2931900090
• European Community (EC) Number: 626-587-9
• NSC Number: 135193
• DSSTox Substance ID: DTXSID20300175
• Nikkaji Number: J410.642C
• Mol file: 29668-61-9.mol

Synonyms:Diethyl (1-cyanoethyl)phosphonate;29668-61-9;diethyl(1-cyanoethyl)phosphonate;2-diethoxyphosphorylpropanenitrile;Phosphonic acid, P-(1-cyanoethyl)-, diethyl ester;diethyl 1-cyanoethylphosphonate;NSC135193;(1-Cyanoethyl)phosphonic acid diethyl ester;Phosphonic acid, (1-cyanoethyl)-, diethyl ester;SCHEMBL124930;2-(diethylphosphono)propionitrile;2-diethoxyphosphoryl-propionitrile;diethyl(1-cyanoethyl)-phosphonate;DTXSID20300175;UMLWEPGSWQNXQX-UHFFFAOYSA-N;diethyl-(1-cyanoethyl)-phosphonate;MFCD01457302;AKOS015912609;AB09137;AT32504;NSC-135193;Diethyl (1-cyanoethyl)phosphonate, 97%;AS-68306;BENZYL-2,3,4,5,6-D5CHLORIDE;FT-0737593;Phosphonic acid,p-(1-cyanoethyl)-,diethyl ester;A929559;J-017594

Chemical Property of Diethyl (1-cyanoethyl)phosphonate

Chemical Property:

• Vapor Pressure: 0.004mmHg at 25°C
• Refractive Index: n20/D 1.432(lit.)
• Boiling Point: 279.5°Cat760mmHg
• Flash Point: 122.8°C
• PSA: 69.13000
• Density: 1.094g/cm³
• LogP: 2.16458
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 191.07113031
• Heavy Atom Count: 12
• Complexity: 210

Purity/Quality:

98%,99%, ^*data from raw suppliers

Diethyl (1-cyanoethyl)phosphonate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOP(=O)(C(C)C#N)OCC
• Uses: NSC 135193 is an intermediate in the synthesis of 4-(1-Cyanoethyl)-1,2,3,4-tetrahydronaphthalene-1-carbonitrile (C979545), a component of the crude extract resulting from studies on the antifungal activity of Citrullus colocynthis against various plant pathogenic fungi.Oligomeric product in thermal polymerization of acrylonitrile/styrene system.

Technology Process of Diethyl (1-cyanoethyl)phosphonate

There total 5 articles about Diethyl (1-cyanoethyl)phosphonate 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: 94.0%

diethyl chlorophosphate (814-49-3) + propiononitrile (107-12-0) → diethyl (1-cyanoethyl)phosphonate (29668-61-9)

Guidance literature:

propiononitrile; With lithium diisopropyl amide; In tetrahydrofuran; hexane; cyclohexane; at -78 ℃; for 0.25h; Inert atmosphere;

diethyl chlorophosphate; In tetrahydrofuran; hexane; cyclohexane; at -78 - 20 ℃; for 1.16667h; Inert atmosphere;

DOI:10.1021/ja3007929

Reference yield: 74.0%

diethyl 1-cyanomethylphosphonate (2537-48-6) + methyl iodide (74-88-4) → diethyl (1-cyanoethyl)phosphonate (29668-61-9)

Guidance literature:

diethyl 1-cyanomethylphosphonate; With sodium hydride; In 1,2-dimethoxyethane; at -10 ℃; for 0.75h;

methyl iodide; In 1,2-dimethoxyethane; at -10 - 20 ℃; for 17.5h;

DOI:10.1055/s-2000-6315

Reference yield:

triethyl phosphite (122-52-1) + 2-bromopropionitrile (19481-82-4) → diethyl (1-cyanoethyl)phosphonate (29668-61-9)

Guidance literature:

DOI:10.1021/jo00872a043

upstream raw materials:

triethyl phosphite

2-bromopropionitrile

diethyl chlorophosphate

propiononitrile

Downstream raw materials:

(Z)-2,4-Dimethyl-3-phenyl-pent-2-enenitrile

(E)-2,4-Dimethyl-3-phenyl-pent-2-enenitrile

Refernces

• 1、 -. "IRAK DEGRADERS AND USES THEREOF". Paragraph 00920; 002836-002838. . Retrieved 2021/01/23.
• 2、 Sovdat, Tina,Bassolino, Giovanni,Liebel, Matz,Schnedermann, Christoph,Fletcher, Stephen P.,Kukura, Philipp. "Backbone modification of retinal induces protein-like excited state dynamics in solution". supporting information; experimental part. p. 8318 - 8320. Retrieved 2012/06/30.