Diethyl itaconate

Base Information

• Chemical Name: Diethyl itaconate
• CAS No.: 2409-52-1
• Molecular Formula: C9H14 O4
• Molecular Weight: 186.208
• Hs Code.: 2917190090
• European Community (EC) Number: 607-321-0
• NSC Number: 67389,1794
• UNII: QP6YYJ8SBB
• DSSTox Substance ID: DTXSID5062390
• Nikkaji Number: J13.295K
• Wikidata: Q72486705
• Mol file: 2409-52-1.mol

Synonyms:Diethyl itaconate;2409-52-1;Itaconic acid diethyl ester;Diethyl 2-methylenesuccinate;diethyl 2-methylidenebutanedioate;Butanedioic acid, methylene-, diethyl ester;Succinic acid, methylene-, diethyl ester;QP6YYJ8SBB;1,4-diethyl 2-methylidenebutanedioate;CCRIS 9508;NSC 1794;NSC-1794;Butanedioic acid, 2-methylene-, 1,4-diethyl ester;NSC 67389;NSC-67389;AI3-11186;Itaconic acid diethyl;UNII-QP6YYJ8SBB;Diethyl Itaconate-13C5;SCHEMBL60515;Diethyl 2-methylenesuccinate #;DIETHYL METHYLENESUCCINATE;DTXSID5062390;NSC1794;BCP22464;CAA40952;NSC67389;ITACONIC ACID, DIETHYL ESTER;MFCD00059230;AKOS006227600;AS-59420;Butanedioic acid, 2-methylene, diethyl ester;CS-0205160;FT-0656585;I0204;D91100;(METHYLENE)BUTANEDIOIC ACID DIETHYL ESTER;27615-38-9

Chemical Property of Diethyl itaconate

Chemical Property:

• Vapor Pressure: 0.0752mmHg at 25°C
• Melting Point: 58.5°C
• Refractive Index: 1.4370 to 1.4400
• Boiling Point: 228°Cat760mmHg
• Flash Point: 108°C
• PSA: 52.60000
• Density: 1.04g/cm³
• LogP: 1.05890
• Storage Temp.: 2-8°C
• Solubility.: soluble in Ethanol,Acetone,Ether,Benzene
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 186.08920892
• Heavy Atom Count: 13
• Complexity: 208

Purity/Quality:

97% ^*data from raw suppliers

2-?Methylene-butanedioicacid1,?4-?diethylester ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CC(=C)C(=O)OCC
• Uses: 2-?Methylene-butanedioic acid 1,?4-?diethyl ester has been used in organic reactions such as the Diels-?Alder reaction.

Technology Process of Diethyl itaconate

There total 21 articles about Diethyl itaconate 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%

2-nitromethyl-1,4-diethyl succinate (4753-28-0) → diethylitaconate (2409-52-1)

Guidance literature:

With sodium tetrahydroborate; In methanol; Reagent/catalyst; Reflux;

DOI:10.1016/j.tet.2017.12.002

Reference yield: 96.0%

ethanol (64-17-5) + 2-methylenesuccinic acid (97-65-4,25119-64-6) → 2-methylene-succinic acid 4-ethyl ester (57718-07-7) + diethylitaconate (2409-52-1)

Guidance literature:

With samarium(III) chloride; at 80 ℃; for 17h; chemoselective reaction; sealed tube; Inert atmosphere;

DOI:10.1021/ol200247c

Reference yield: 95.0%

ethanol (64-17-5) + 2-methylenesuccinic acid (97-65-4,25119-64-6) → diethylitaconate (2409-52-1)

Guidance literature:

With sulfuric acid; at 150 ℃; for 4h;

DOI:10.1016/S0040-4020(01)81120-0

upstream raw materials:

ethanol

2-methylenesuccinic acid

diethyl citraconate

sodium ethanolate

Downstream raw materials:

Diethyl 2-methylsuccinate

diethyl oxaloacetate

(2-nitro-ethyl)-succinic acid diethyl ester

butane-1,1,2,3-tetracarboxylic acid tetraethyl ester