Dimethyl 2-phenylbutanedioate

Base Information

• Chemical Name: Dimethyl 2-phenylbutanedioate
• CAS No.: 15463-92-0
• Molecular Formula: C12H14O4
• Molecular Weight: 222.241
• Hs Code.: 2917399090
• DSSTox Substance ID: DTXSID60342554
• Nikkaji Number: J47.511D
• Mol file: 15463-92-0.mol

Synonyms:dimethyl 2-phenylbutanedioate;15463-92-0;Butanedioic acid, phenyl-, dimethyl ester;Dimethyl phenylsuccinate;Succinic acid, phenyl-, dimethyl ester;Dimethyl 2-phenylsuccinate;dimethyl2-phenylbutanedioate;CBiol_000817;CBiol_000839;Dimethyl 2-phenylsuccinate #;2-Phenylsuccinic acid dimethyl;SCHEMBL6390962;DTXSID60342554;ICCB4_000113;ICCB4_000135;ICCB6_000213;2-(Phenyl)succinic acid dimethyl ester;SB49693;2-phenyl-butanedioic acid dimethyl ester;PHENYLSUCCINIC ACID DIMETHYL ESTER;BCB03_000005;BS-27531

Chemical Property of Dimethyl 2-phenylbutanedioate

Chemical Property:

• Melting Point: 54.5-55.5 °C
• Boiling Point: 301.7±22.0 °C(Predicted)
• PSA: 52.60000
• Density: 1.133±0.06 g/cm3(Predicted)
• LogP: 1.50630
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 222.08920892
• Heavy Atom Count: 16
• Complexity: 243

Purity/Quality:

99% ^*data from raw suppliers

Dimethyl2-phenylbutanedioate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)CC(C1=CC=CC=C1)C(=O)OC

Technology Process of Dimethyl 2-phenylbutanedioate

There total 87 articles about Dimethyl 2-phenylbutanedioate 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: 88.0%

methanol (67-56-1) + carbon monoxide (201230-82-2) + phenylacetylene (536-74-3) → dimethyl 2-phenylsuccinate (15463-92-0) + methyl cinnamate (103-26-4,1754-62-7)

Guidance literature:

With 1,3-bis(tert-butyl(pyridin-2-yl)phosphanyl)propane; palladium(II) acetylacetonate; toluene-4-sulfonic acid; at 120 ℃; for 20h; under 30003 Torr; Reagent/catalyst; Sealed tube;

DOI:10.1021/jacs.8b05852

Reference yield: 45.0%

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + methanol (67-56-1) + carbon monoxide (201230-82-2) → dimethyl 2-phenylsuccinate (15463-92-0) + acetophenone (98-86-2)

Guidance literature:

With methanesulfonic acid; air; ammonium chloride; palladium diacetate; NPMoV; at 60 ℃; for 16h; under 15201 Torr;

DOI:10.1021/jo0255779

Reference yield: 41.0%

Methyl cinnamate (103-26-4,1754-62-7) → 3-phenylpropanoic acid methyl ester (103-25-3) + dimethyl 2-phenylsuccinate (15463-92-0)

Guidance literature:

With methyl chloroformate; In acetonitrile; -1.9 V (mercury cathode, SCE), Et₄NClO₄;

DOI:10.1021/jo00165a013

upstream raw materials:

methanol

2-phenylsuccinic acid

diethyl ether

dimethyl cis-but-2-ene-1,4-dioate

Downstream raw materials:

3,4-diphenyl-but-3-enoic acid

4-oxo-2-phenyl-butyric acid

2-phenylsuccinaldehyde

2,N-diphenyl-succinamic acid

Refernces

• 1、 Ji, Xiaolei,Shen, Chaoren,Tian, Xinxin,Dong, Kaiwu. "Palladium-Catalyzed Asymmetric Hydroesterification of α-Aryl Acrylic Acids to Chiral Substituted Succinates". supporting information. p. 8645 - 8649. Retrieved 2021/10/25.
• 2、 Dixit, Manish K.,Dubey, Mrigendra,Kalam, Abul,Kumar, Yeeshu,Mahendar, Chinthakuntla,Sharma, Vinay K.,Shukla, Jay. "Investigation of the Mechanism Behind Conductive Fluorescent and Multistimuli-responsive Li+-enriched Metallogel Formation". . p. 3020 - 3028. Retrieved 2020/09/04.