DIETHYL (2-OXO-2-PHENYLETHYL)PHOSPHONATE

Base Information

• Chemical Name: DIETHYL (2-OXO-2-PHENYLETHYL)PHOSPHONATE
• CAS No.: 3453-00-7
• Molecular Formula: C12H17O4P
• Molecular Weight: 256.238
• Hs Code.: 2931900090
• Mol file: 3453-00-7.mol

Synonyms:Phosphonicacid, (2-oxo-2-phenylethyl)-, diethyl ester (9CI);Phosphonic acid, phenacyl-,diethyl ester (6CI,7CI,8CI);(2-Oxo-2-phenylethyl)phosphonic acid diethylester;Diethyl (2-oxo-2-phenylethyl)phosphonate;Diethyl(2-oxophenethyl)phosphonate;Diethyl 2-oxo-2-phenylethanephosphonate;Diethylbenzoylmethanephosphonate;Diethyl benzoylmethylphosphonate;Diethylphenacylphosphonate;NSC 648426;

Chemical Property of DIETHYL (2-OXO-2-PHENYLETHYL)PHOSPHONATE

Chemical Property:

• Vapor Pressure: 9.01E-06mmHg at 25°C
• Refractive Index: n20/D 1.513(lit.)
• Boiling Point: 373.4 °C at 760 mmHg
• Flash Point: 193.2 °C
• PSA: 62.41000
• Density: 1.144 g/cm³
• LogP: 3.13540

Purity/Quality:

99% ^*data from raw suppliers

Diethyl (2-Oxo-2-phenylethyl)phosphonate >97.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: Reactant involved in:Asymmetric Michael addition of β-oxo phosphonates to nitro olefinsGem-chlorofluorination of keto phosphonates with subsequent functionalization of the productsCyclocondensation reactions to produce arylphosphonatesDiazo transfer reactions for synthesis of diazo-phosphonyl compoundsHorner-Wadsworth-Emmons reactionsInverse-electron-demand Diels-Alder reactions

Technology Process of DIETHYL (2-OXO-2-PHENYLETHYL)PHOSPHONATE

There total 106 articles about DIETHYL (2-OXO-2-PHENYLETHYL)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: 96.0%

diethyl phenylethynylphosphonate (3450-67-7) → diethyl benzoylmethylphosphonate (3453-00-7)

Guidance literature:

With 2-dicyclohexylphosphino-2’,4’,6’-triisopropylbiphenyl gold(I) bis(trifluoromethanesulfonyl)imide; water; In 1,2-dichloro-ethane; at 20 ℃; for 12h; Reagent/catalyst; Solvent; regioselective reaction;

DOI:10.1002/ejoc.201400066

Reference yield: 96.0%

benzoic acid methyl ester (93-58-3,5705-52-2,80226-58-0) + Diethyl methylphosphonate (683-08-9) → diethyl benzoylmethylphosphonate (3453-00-7)

Guidance literature:

benzoic acid methyl ester; Diethyl methylphosphonate; In tetrahydrofuran; at 0 ℃; for 0.5h; Inert atmosphere;

With lithium diisopropyl amide; In tetrahydrofuran; at 0 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/jacs.6b06390

Reference yield: 92.0%

(E)-3-phenylacrylic acid (140-10-3) + phosphonic acid diethyl ester (762-04-9) → diethyl benzoylmethylphosphonate (3453-00-7)

Guidance literature:

With copper(ll) sulfate pentahydrate; oxygen; In acetonitrile; at 60 ℃; for 6h; Reagent/catalyst; Solvent; Temperature;

DOI:10.1016/j.tet.2017.03.026

upstream raw materials:

diethyl ether

sodium diethyl phosphite

α-bromoacetophenone

triethyl phosphite

Downstream raw materials:

diethyl (1-bromo-2-oxo-2-phenylethyl)phosphonate

diethyl (2-amino-2-phenylethyl)phosphonate

2-diazo-2-diphenylphosphinoyl-1-phenyl-ethanone

2-amino-2-phenylethylphosphonic acid

Refernces

• 1、 Xiong, Yu,Wang, Shibin,Chen, Wenxing,Zhang, Jian,Li, Qiheng,Hu, Han-Shi,Zheng, Lirong,Yan, Wensheng,Gu, Lin,Wang, Dingsheng,Li, Yadong. "Construction of Dual-Active-Site Copper Catalyst Containing both Cu-N3 and Cu-N4 Sites". . . Retrieved 2021.
• 2、 Huang, Peipei,Xu, Jiaxi. "Synthesis of 2-oxophosphorindolines: Via the copper-catalyzed intramolecular aromatic C-H insertion of diazophosphonamidates". . p. 63736 - 63748. Retrieved 2016.
• 3、 Maciás-Benítez, Pablo,Sierra-Padilla, Alfonso,Tenorio, Manuel J.,Moreno-Dorado, F. Javier,Guerra, Francisco M.. "Copper-Catalyzed Microwave-Expedited Oxyphosphorylation of Alkynes with Diethyl Phosphite and t-Butyl Hydroperoxide Synthesis of Densely Functionalized Phosphonylated Indenones". . p. 16409 - 16424. Retrieved 2021/11/16.