Diethyl (3-cyanophenyl)phosphonate

Base Information

• Chemical Name: Diethyl (3-cyanophenyl)phosphonate
• CAS No.: 85915-09-9
• Molecular Formula: C11H14 N O3 P
• Molecular Weight: 239.211
• Hs Code.: 2931900090
• DSSTox Substance ID: DTXSID90517819
• Wikidata: Q82380024
• Mol file: 85915-09-9.mol

Synonyms:85915-09-9;Diethyl (3-cyanophenyl)phosphonate;Diethyl 3-cyanophenylphosphonate;(3-CYANO-PHENYL)-PHOSPHONIC ACID DIETHYL ESTER;SCHEMBL12254803;DTXSID90517819;MFCD09029594;AKOS015962718;SY311966;(3-CYANO-PHENYL)-PHOSPHONICACIDDIETHYLESTER;J-520293

Chemical Property of Diethyl (3-cyanophenyl)phosphonate

Chemical Property:

• PSA: 69.13000
• LogP: 2.44968
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 239.07113031
• Heavy Atom Count: 16
• Complexity: 300

Purity/Quality:

99%min ^*data from raw suppliers

(3-CYANO-PHENYL)-PHOSPHONIC ACID DIETHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOP(=O)(C1=CC=CC(=C1)C#N)OCC

Technology Process of Diethyl (3-cyanophenyl)phosphonate

There total 8 articles about Diethyl (3-cyanophenyl)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: 85.0%

3-cyanobromobenzene (6952-59-6) + phosphonic acid diethyl ester (762-04-9) → 3-Cyanphenylphosphonsaeurediethylester (85915-09-9)

Guidance literature:

With dicyclohexylmethylamine; triphenylphosphine; palladium diacetate; In ethanol; at 76 ℃; for 16h;

DOI:10.1055/s-2005-862372

Reference yield: 85.0%

4-cyanophenyl sulfurofluoridate + phosphonic acid diethyl ester (762-04-9) → 3-Cyanphenylphosphonsaeurediethylester (85915-09-9)

Guidance literature:

With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 80 ℃; for 5h; Sealed tube;

DOI:10.1039/d1cc00769f

Reference yield: 78.0%

3-cyanophenyl-4-methylbenzene-1-sulfonate (49584-07-8) + phosphonic acid diethyl ester (762-04-9) → 3-Cyanphenylphosphonsaeurediethylester (85915-09-9)

Guidance literature:

With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; 2-(di-tert-butylphosphaneyl)-4-methoxy-N,N-dimethylaniline; N-ethyl-N,N-diisopropylamine; In toluene; at 110 ℃; for 30h; Inert atmosphere; Schlenk technique;

DOI:10.1134/S1070363220040258

upstream raw materials:

benzonitrile

phosphonic acid diethyl ester

3-cyanobromobenzene

triethyl phosphate

Refernces

• 1、 Li, Chun-jing. "Nickel-Catalyzed Phosphorylation of Tosylates". . p. 725 - 730. Retrieved 2020/06/30.
• 2、 Khrizanforov,Strekalova,Kholin,Khrizanforova,Kadirov,Gryaznova,Budnikova. "Novel approach to metal-induced oxidative phosphorylation of aromatic compounds". . p. 133 - 141. Retrieved 2016/11/03.