Diethyl (2-cyanoethyl)phosphonate

Base Information

• Chemical Name: Diethyl (2-cyanoethyl)phosphonate
• CAS No.: 10123-62-3
• Molecular Formula: C7H14 N O3 P
• Molecular Weight: 191.167
• Hs Code.: 2931900090
• European Community (EC) Number: 233-327-4
• NSC Number: 74863,43781
• DSSTox Substance ID: DTXSID80143803
• Nikkaji Number: J43.004H
• Wikidata: Q83007804
• Mol file: 10123-62-3.mol

Synonyms:Diethyl (2-cyanoethyl)phosphonate;10123-62-3;3-diethoxyphosphorylpropanenitrile;Diethyl 2-cyanoethanephosphonate;NSC 43781;NSC 74863;Phosphonic acid, (2-cyanoethyl)-, diethyl ester;2-Cyanoethanephosphonic acid diethyl ester;EINECS 233-327-4;Ethanephosphonic acid, 2-cyano-, diethyl ester;beta-(Diethoxyphosphinyl)propionitrile;BRN 1775584;Phosphonic acid, P-(2-cyanoethyl)-, diethyl ester;AI3-16155;diethyl(2-cyanoethyl)phosphonate;4-04-00-03620 (Beilstein Handbook Reference);WLN: NC2PO&O2&O2;.beta.-(Diethoxyphosphinyl)propionitrile;diethyl 2-cyanoethylphosphonate;3-(Diethylphosphono)propionitrile;(2-Cyanoethyl)-phosphonic acid diethyl ester;diethyl cyanoethylphosphonate;NCIOpen2_000815;C7H14NO3P;SCHEMBL491513;DTXSID80143803;C7-H14-N-O3-P;NSC43781;NSC74863;3-(Diethoxyphosphinyl)propiononitrile;BBL100161;NSC-43781;NSC-74863;STL512128;AKOS015916240;O,O-diethyl (2-cyanoethyl)phosphonate;Diethyl (2-cyanoethyl)phosphonate, 95%;AS-68304;LS-65585;CS-0362849;(2-Cyano-ethyl)-phosphonic acid diethyl ester;DIETHYL (2-CYANOETHYL)PHOSPHONATE 95;EN300-1722908;J-000347

Chemical Property of Diethyl (2-cyanoethyl)phosphonate

Chemical Property:

• Vapor Pressure: 0.000928mmHg at 25°C
• Refractive Index: n20/D 1.4380(lit.)
• Boiling Point: 303.5°Cat760mmHg
• Flash Point: 137.3°C
• PSA: 78.36000
• Density: 1.096g/cm³
• LogP: 2.09778
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 191.07113031
• Heavy Atom Count: 12
• Complexity: 198

Purity/Quality:

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

Diethyl (2-cyanoethyl)phosphonate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOP(=O)(CCC#N)OCC
• Uses: Diethyl (2-cyanoethyl)phosphonate, is a useful reactant used in various chemical synthesis such as in synthesis of lipophilic oxoamides with activity against phospholipase A2, Triose phosphate isomerase of muscle inhibitors, and also in base-catalyzed stereospecific anti-Markovnikov addition. Reactant for:Heteroatom-directed alkyl cyanation of alkynesUse as a fluorescent substrate for carbon-phosphorous lyaseMicrowave-assisted cleavage of phosphate, phosphonate, and phorphoramide estersAmination and stereoselective olefination for synthesis of HIV-1 antiviralsReactant for synthesis of: Base-catalyzed stereospecific anti-Markovnikov addition reactantsLipophilic oxoamides with activity against phospholipase A2Triose phosphate isomerase of muscle inhibitors

Technology Process of Diethyl (2-cyanoethyl)phosphonate

There total 19 articles about Diethyl (2-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: 99.0%

acrylonitrile (107-13-1,25014-41-9) + phosphonic acid diethyl ester (762-04-9) → diethyl (2-cyanoethyl)phosphonate (10123-62-3)

Guidance literature:

With 1,3-dicyclohexylimidazolium-2-carboxylate; In tetrahydrofuran; at 21 ℃; for 2h;

DOI:10.1021/jo500108a

Reference yield: 85.0%

3-Chloropropionitrile (542-76-7) + triethyl phosphite (122-52-1) → diethyl (2-cyanoethyl)phosphonate (10123-62-3)

Guidance literature:

for 3h; Heating;

DOI:10.1080/10426500008043648

Reference yield: 74.0%

thiophosphoric acid S-[2-(2-bromo-phenyl)-ethyl] ester O,O'-diethyl ester (934538-82-6) + acrylonitrile (107-13-1,25014-41-9) → diethyl (2-cyanoethyl)phosphonate (10123-62-3)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; for 1h; Heating;

DOI:10.1021/ol0631096

upstream raw materials:

3-Chloropropionitrile

sodium diethyl phosphite

acrylonitrile

phosphonic acid diethyl ester

Downstream raw materials:

3-phosphonopropionic acid

diethyl 3-aminopropan-1-ylphosphonate

α-Amino-γ-diaethylphosphonopropyliden>-α,α-diphosphonsaeure

1-(diethoxyphosphinyl)-3-hexanone

Refernces

• 1、 Fonvielle,Mariano,Therisod. "New inhibitors of rabbit muscle triose-phosphate isomerase". . p. 2906 - 2909. Retrieved 2005.
• 2、 Wozniak, Lucyna A.,Bukowiecka-Matusiak, Malgorzata,Burzynska-Pedziwatr, Izabela,Stec, Wojciech J.. "Stereodefined dinucleoside (3′,5′)-propionamidophosphonates and β-cyanoethylphosphonates and their incorporation into modified oligonucleotides". . p. 2620 - 2623. Retrieved 2009.
• 3、 Salin, Alexey V.,Il’in, Anton V.. "Comparison of catalytic activity of hexamethyltriamino- and tri-n-butylphosphines in the Pudovik reaction". . p. 355 - 356. Retrieved 2019.
• 4、 Villemin, Didier,Racha, Rassem. "ACTIVATION ANIONIQUE DU PHOSPHITE DE DIETHYLE PAR LE FLUORURE DE POTASSIUM DEPOSE SUR ALUMINE, SYNTHESE DE PHOSPHONATES FONCTIONALISES". . p. 1789 - 1790. Retrieved 1986.
• 5、 Bochwic,Michalski. "-". . p. 1035. Retrieved 1951.
• 6、 Ivanov,B.E. et al.. "-". . . Retrieved 1967.
• 7、 Simoni, Daniele,Invidiata, Francesco Paolo,Manferdini, Monica,Lampronti, Ilaria,Rondanin, Riccardo,Roberti, Marinella,Pollini, Gian Piero. "Tetramethylguanidine (TMG)-catalyzed addition of dialkyl phosphites to α,β-unsaturated carbonyl compounds, alkenenitriles, aldehydes, ketones and imines". . p. 7615 - 7618. Retrieved 1998.
• 8、 Huang, Tian-Zeng,Chen, Tieqiao,Saga, Yuta,Han, Li-Biao. "Me3P-catalyzed addition of hydrogen phosphoryl compounds P(O)H to electron-deficient alkenes: 1 to 1 vs 1 to 2 adducts". . p. 7085 - 7093. Retrieved 2017/11/13.