Dimethyl (2-oxo-4-phenylbutyl)phosphonate

Base Information

• Chemical Name: Dimethyl (2-oxo-4-phenylbutyl)phosphonate
• CAS No.: 41162-19-0
• Molecular Formula: C12H17O4P
• Molecular Weight: 256.238
• Hs Code.: 2931900090
• European Community (EC) Number: 682-093-3
• DSSTox Substance ID: DTXSID50370063
• Nikkaji Number: J2.755.107F
• Wikidata: Q72471127
• Mol file: 41162-19-0.mol

Synonyms:Dimethyl (2-oxo-4-phenylbutyl)phosphonate;41162-19-0;Dimethyl 2-Oxo-4-phenylbutylphosphonate;1-dimethoxyphosphoryl-4-phenylbutan-2-one;Phosphonic acid, (2-oxo-4-phenylbutyl)-, dimethyl ester;Dimethyl(2-oxo-4-phenylbutyl)phosphonate;SCHEMBL187684;PhCH2CH2COCH2PO(OMe)2;DTXSID50370063;ONYIBVIIOCEBIV-UHFFFAOYSA-N;AMY24740;BCP21712;MFCD02093040;AKOS016009822;AC-5956;dimethyl-(2-oxo-4-phenylbutyl)phosphonate;dimethyl (2-oxo-4-phenylbutyl)-phosphonate;CS-0150155;FT-0652507;2-Oxo-4-phenylbutylphosphonic acid dimethyl ester;J-520359;(2-oxo-4-phenyl-butyl)-phosphonic acid dimethyl ester

Chemical Property of Dimethyl (2-oxo-4-phenylbutyl)phosphonate

Chemical Property:

• Appearance/Colour: clear yellow liquid
• Vapor Pressure: 1.9E-05mmHg at 25°C
• Melting Point: 120-122 (0.5 MMHG)oC
• Refractive Index: 1.494
• Boiling Point: 362.7 °C at 760 mmHg
• Flash Point: 186.8 °C
• PSA: 62.41000
• Density: 1.152 g/cm³
• LogP: 2.67420
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: Chloroform (Sparingly), Methanol (Slightly)
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 256.08644602
• Heavy Atom Count: 17
• Complexity: 276

Purity/Quality:

99% ^*data from raw suppliers

Dimethyl (2-oxo-4-phenylbutyl)phosphonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COP(=O)(CC(=O)CCC1=CC=CC=C1)OC
• Uses: Dimethyl (2-Oxo-4-phenylbutyl)phosphonate (Bimatoprost Impurity 12) is an impurity of Bimatoprost (B386800), an antiglaucoma agent. Bimatoprost is also a synthetic prostamide; structurally related to prostaglandin F2α.

Technology Process of Dimethyl (2-oxo-4-phenylbutyl)phosphonate

There total 14 articles about Dimethyl (2-oxo-4-phenylbutyl)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: 98.0%

3-phenylpropanoic acid methyl ester (103-25-3) + dimethyl methane phosphonate (756-79-6) → dimethyl(2-oxo-4-phenylbutyl)phosphonate (41162-19-0)

Guidance literature:

dimethyl methane phosphonate; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere;

3-phenylpropanoic acid methyl ester; In tetrahydrofuran; at -78 ℃; for 1h;

Reference yield: 95.0%

ethyl dihydrocinnamate (2021-28-5) + dimethyl methane phosphonate (756-79-6) → dimethyl(2-oxo-4-phenylbutyl)phosphonate (41162-19-0)

Guidance literature:

With n-butyllithium; diisopropylamine; In tetrahydrofuran; at 5 - 20 ℃; Inert atmosphere;

DOI:10.3762/bjoc.13.149

Reference yield: 85.0%

argon + 1-iodo-4-phenylbutan-2-one (352276-27-8) → dimethyl(2-oxo-4-phenylbutyl)phosphonate (41162-19-0)

Guidance literature:

With phosphorous acid trimethyl ester; In acetonitrile;

upstream raw materials:

dimethyl (2-oxopropyl)phosphonate

benzyl chloride

ethyl dihydrocinnamate

dimethyl methane phosphonate

Downstream raw materials:

C₄₄H₈₂O₅Si₃

Refernces

• 1、 Wang, Congcong,Zhang, Yu-Fang,Guo, Shimeng,Zhao, Quan,Zeng, Yanping,Xie, Zhicheng,Xie, Xin,Lu, Boxun,Hu, Youhong. "GPR52 Antagonist Reduces Huntingtin Levels and Ameliorates Huntington's Disease-Related Phenotypes". . p. 941 - 957. Retrieved 2020/11/30.
• 2、 Hamada, Yoko,Kawasaki-Takasuka, Tomoko,Yamazaki, Takashi. "Base-promoted isomerization of CF3-containing allylic alcohols to the corresponding saturated ketones under metal-free conditions". supporting information. p. 1507 - 1512. Retrieved 2017/08/14.