Methyl 2-oxocyclopentanecarboxylate

Base Information

• Chemical Name: Methyl 2-oxocyclopentanecarboxylate
• CAS No.: 10472-24-9
• Deprecated CAS: 53229-93-9
• Molecular Formula: C7H10O3
• Molecular Weight: 142.155
• Hs Code.: 29183000
• European Community (EC) Number: 233-962-7
• DSSTox Substance ID: DTXSID50884473
• Nikkaji Number: J151.110F
• Mol file: 10472-24-9.mol

Synonyms:10472-24-9;Methyl 2-oxocyclopentanecarboxylate;Methyl 2-cyclopentanonecarboxylate;2-carbmethoxycyclopentanone;methyl 2-oxocyclopentane-1-carboxylate;Methyl cyclopentanone-2-carboxylate;Cyclopentanecarboxylic acid, 2-oxo-, methyl ester;MFCD00001411;2-Methoxycarbonylcyclopentanone;EINECS 233-962-7;2-Oxocyclopentanecarboxylic Acid Methyl Ester;methyl-2-oxocyclopentane carboxylate;methyl-2-oxocyclopentanecarboxylate;methyl-2-oxocyclopentanoate;SCHEMBL25061;2-methoxycarbonylcylopentanone;2-Methoxycarbonyl-cyclopentanone;methyl2-cyclopentanonecarboxylate;DTXSID50884473;methyl-2-oxocylopentanecarboxylate;Methy 2-oxocyclopentanecarboxylate;Methylcyclopentanone-2-carboxylate;BCP23209;methyl 2-oxo-cyclopentanecarboxylate;methyl 2-oxocyclo-pentanecarboxylate;methyl 2-oxocyclopentane carboxylate;methyl 2-oxocyclopentane-carboxylate;STR04302;Methyl-2-oxo-cyclopentanecarboxylate;AC-974;BBL027341;FD9017;STK802142;AKOS005622625;methyl 2-oxo-1-cyclopentanecarboxylate;PB47456;2-oxocyclopentanecarboxylate methyl ester;Methyl 2-oxocyclopentanecarboxylate, 95%;SY006366;AM20070696;CS-0007582;FT-0628724;2-oxo-cyclopentanecarboxylic acid methyl ester;Cyclopentanone-2-carboxylic Acid Methyl Ester;EN300-103267;Q-103266;F9995-1304;Z1255356032

Chemical Property of Methyl 2-oxocyclopentanecarboxylate

Chemical Property:

• Appearance/Colour: clear colorless to slight yellowish liquid
• Vapor Pressure: 0.2mmHg at 25°C
• Melting Point: 123-125 °C
• Refractive Index: n20/D 1.456(lit.)
• Boiling Point: 209.7 °C at 760 mmHg
• PKA: 12.00±0.20(Predicted)
• Flash Point: 84 °C
• PSA: 43.37000
• Density: 1.157 g/cm³
• LogP: 0.52860
• Storage Temp.: 2-8°C
• Solubility.: Chloroform, Ethyl Acetate
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 142.062994177
• Heavy Atom Count: 10
• Complexity: 162

Purity/Quality:

99.5% ^*data from raw suppliers

Methyl2-Cyclopentanonecarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-10
• Safety Statements: 23-24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1CCCC1=O
• Uses: Methyl 2-Cyclopentanonecarboxylate is used in the synthesis of functionalized ketones.

Technology Process of Methyl 2-oxocyclopentanecarboxylate

There total 26 articles about Methyl 2-oxocyclopentanecarboxylate 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: 100.0%

cyclopentanone (120-92-3) + carbonic acid dimethyl ester (616-38-6) → methyl 2-oxocyclopentane-1-carboxylate (10472-24-9,265317-94-0)

Guidance literature:

carbonic acid dimethyl ester; With sodium hydride; In toluene; mineral oil; for 1h; Reflux;

cyclopentanone; In toluene; mineral oil; for 3h; Reflux;

Reference yield: 99.0%

hexanedioic acid dimethyl ester (627-93-0) → methyl 2-oxocyclopentane-1-carboxylate (10472-24-9,265317-94-0)

Guidance literature:

With hydrogenchloride; copper(ll) bromide; lithium diisopropyl amide; In tetrahydrofuran; hexane; 1.) -78 deg C, 30 min; -78 deg C, 15 min, 2.) RT;

DOI:10.1021/jo00155a047

Reference yield: 97.0%

methyl 1-hydroxy-2-oxo-cyclopentanecarboxylate (151930-48-2) → methyl 2-oxocyclopentane-1-carboxylate (10472-24-9,265317-94-0)

Guidance literature:

With samarium diiodide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at 0 ℃;

DOI:10.1016/j.tetlet.2006.09.071

upstream raw materials:

hexanedioic acid dimethyl ester

sodium methylate

acetophenone

diazomethane

Downstream raw materials:

2-m-Methoxybenzyl-2-methoxycarbonylcyclopentanon

Methyl-2-oxo-1-(phenyl-thio)cyclo-pentan-carboxylat

methyl 2-(1-piperidinyl) 1-cyclopentenecarboxylate

methyl cyclopentanone-2-carboxylate diethylketal

Refernces

• 1、 Hong, Xuechuan,Mejía-Oneto, José M.,Padwa, Albert. "Lewis acid-promoted α-hydroxy β-dicarbonyl to α-ketol ester rearrangement". . p. 8387 - 8390. Retrieved 2006.
• 2、 Raftery, Mark J.,Bowie, John H.. "Does the Dieckmann Condensation Occur in the Gas Phase ?". . p. 719 - 722. Retrieved 1988.
• 3、 Mayer,Kubasch. "-". . p. 43. Retrieved 1959.
• 4、 Chen, Pengli,Fu, Yang,Hu, Yanqin,Wang, Shuaifei,Wang, Yakun,Zhang, Conghui,Zhang, Mingwei,Zhao, Ting. "Highly Selective Difluoromethylations of β-Keto Amides with -TMSCF 2Br under Mild Conditions". supporting information. p. 1123 - 1130. Retrieved 2021/06/18.
• 5、 -. "INHIBITORS OF LYSINE BIOSYNTHESIS VIA THE DIAMINOPIMELATE PATHWAY". Paragraph 0271. . Retrieved 2020/01/24.