Dimethyl 2-methylenepentanedioate

Base Information

• Chemical Name: Dimethyl 2-methylenepentanedioate
• CAS No.: 5621-44-3
• Molecular Formula: C8H12 O4
• Molecular Weight: 172.181
• DSSTox Substance ID: DTXSID201288491
• Nikkaji Number: J119.735E
• ChEMBL ID: CHEMBL4866827
• Mol file: 5621-44-3.mol

Synonyms:Dimethyl 2-methylenepentanedioate;5621-44-3;dimethyl 2-methylidenepentanedioate;2-METHYLENE-PENTANEDIOIC ACID DIMETHYL ESTER;Pentanedioic acid, 2-methylene-, dimethyl ester;Dimethyl 2-methyleneglutarate;2-Methylenepentanedioic Acid Dimethyl Ester;Glutaric acid, 2-methylene-, dimethyl ester;1,5-DIMETHYL 2-METHYLIDENEPENTANEDIOATE;Methyl methyleneglutarate;Dimethyl2-methylenepentanedioate;SCHEMBL4494873;CHEMBL4866827;DTXSID201288491;1,5-Dimethyl 2-methylenepentanedioate;AKOS006285994;MB05430;2-Methyleneglutaric acid, dimethyl ester;WS-00787;FT-0694959;1-Butene-2,4-dicarboxylic acid dimethyl ester

Chemical Property of Dimethyl 2-methylenepentanedioate

Chemical Property:

• Vapor Pressure: 0.5±0.4 mmHg at 25°C
• Boiling Point: 729.3°Cat760mmHg
• Flash Point: 394.9°C
• PSA: 52.60000
• Density: 1.582g/cm³
• LogP: 0.66880
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 172.07355886
• Heavy Atom Count: 12
• Complexity: 195

Purity/Quality:

99% ^*data from raw suppliers

Dimethyl2-methylenepentanedioate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)CCC(=C)C(=O)OC

Technology Process of Dimethyl 2-methylenepentanedioate

There total 18 articles about Dimethyl 2-methylenepentanedioate 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: 91.0%

acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → dimethyl 2-methylenepentanedioate (5621-44-3)

Guidance literature:

(η5-C5Me5)RuH3(PCy3); In tetrahydrofuran; at 80 ℃; for 24h; Product distribution; dimerization of acrylic carbonyl compounds;

DOI:10.1016/S0022-328X(97)00591-3

Reference yield: 82.0%

Benzyl-[1-methyl-pyrrolidin-(2Z)-ylidene]-amine (32263-20-0) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → dimethyl 2-methylenepentanedioate (5621-44-3) + 3-{2-[(Z)-Benzylimino]-1-methyl-pyrrolidin-3-yl}-propionic acid methyl ester (146698-21-7) + 3-[2-[(Z)-Benzylimino]-3-(2-methoxycarbonyl-ethyl)-1-methyl-pyrrolidin-3-yl]-propionic acid methyl ester (146698-22-8)

Guidance literature:

With hydroquinone; at 150 ℃; for 16h;

DOI:10.1016/S0040-4039(00)60579-8

Reference yield: 40.0%

dimethyl cis-1-bromomethylcyclopropane-1,2-dicarboxylate (114644-51-8,114644-56-3) → dimethyl 2-methylenepentanedioate (5621-44-3)

Guidance literature:

vitamin B₁₂s; for 0.5h;

DOI:10.1039/P29880000061

upstream raw materials:

methyl 3-methoxypropionate

1-Methyl-r-1,t-2-cyclopropandicarbonsaeure-dimethylester

acrylic acid methyl ester

Benzyl-[1-methyl-pyrrolidin-(2Z)-ylidene]-amine

Downstream raw materials:

2-methyleneglutaric acid

(E)-γ-methylglutaconic acid

4,4'-Methylenebis(2,6-di-tert-butylphenol)

4,4'-dihydroxy-3,3',5,5'-tetra-tert-butylbiphenyl