Dimethyl itaconate

Base Information

• Chemical Name: Dimethyl itaconate
• CAS No.: 617-52-7
• Molecular Formula: C7H10O4
• Molecular Weight: 158.154
• Hs Code.: 29171900
• European Community (EC) Number: 210-519-6
• NSC Number: 9385
• UNII: 11JIB0YI93
• DSSTox Substance ID: DTXSID80210701
• Nikkaji Number: J45.119C
• Wikidata: Q63396620
• ChEMBL ID: CHEMBL4750162
• Mol file: 617-52-7.mol

Synonyms:dimethyl itaconate;dimethylitaconate

Chemical Property of Dimethyl itaconate

Chemical Property:

• Appearance/Colour: white crystalline low melting mass or liquid
• Vapor Pressure: 0.219mmHg at 25°C
• Melting Point: 37-41 °C(lit.)
• Refractive Index: 1.428
• Boiling Point: 207.999 °C at 760 mmHg
• Flash Point: 89.094 °C
• PSA: 52.60000
• Density: 1.084 g/cm³
• LogP: 0.27870
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Water Solubility.: slightly soluble
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 158.05790880
• Heavy Atom Count: 11
• Complexity: 183

Purity/Quality:

98%, ^*data from raw suppliers

Dimethyl itaconate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC(=O)CC(=C)C(=O)OC
• Uses: Dimethyl Itaconate is a chemical reagent used in the synthesis of functionalized 2-isoxazolines used in fragment-based drug discovery. Dimethyl itaconate may be used in functionalization of isotactic poly(propylene). It was used in crosslinking of polyesters: poly(isosorbide itaconate)and poly(isosorbide itaconate-co-succinate). Dimethyl itaconate can be used for the rhodium catalyzed asymmetric hydrogenation of (S)-dimethyl-2-methylsuccinate and (R)-methyl succinic acid dimethyl ester.

Technology Process of Dimethyl itaconate

There total 19 articles about Dimethyl 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: 93.07%

methanol (67-56-1) + 2-methylenesuccinic acid (97-65-4,25119-64-6) → Dimethyl itakonate (617-52-7)

Guidance literature:

With La³⁺SO₄^2-/TiO₂-SiO₂; at 120 ℃; for 7h; Reagent/catalyst; Time; Concentration; Autoclave;

DOI:10.1016/j.molcata.2012.11.008

Reference yield: 90.0%

methanol (67-56-1) + 2-methylenesuccinic acid (97-65-4,25119-64-6) → 4-methoxy-2-methylene-4-oxobutanoic acid (7338-27-4) + Dimethyl itakonate (617-52-7)

Guidance literature:

With thionyl chloride; at 25 - 27 ℃; for 19h;

Reference yield: 85.0%

2-methylenesuccinic acid (97-65-4,25119-64-6) + methyl iodide (74-88-4) → Dimethyl itakonate (617-52-7)

Guidance literature:

2-methylenesuccinic acid; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; for 0.166667h;

methyl iodide; In acetonitrile; at 20 ℃; for 4h;

DOI:10.1080/00397910802238809

upstream raw materials:

2-methylenesuccinic acid

dimethyl sulfate

nitromethane

dimethylfumarate

Downstream raw materials:

mesaconic acid dimethyl ester

methyl 2-methylsuccinate

dimethyl ²H₁-methylfumarate

methyl 1-[(4-methoxyphenyl)methyl]-5-oxopyrrolidine-3-carboxylate

Refernces

• 1、 Ohashi, Yasunori,Kan, Yoshihiko,Watanabe, Takahito,Honda, Yoichi,Watanabe, Takashi. "Redox silencing of the Fenton reaction system by an alkylitaconic acid, ceriporic acid B produced by a selective lignin-degrading fungus, Ceriporiopsis subvermispora". . p. 840 - 847. Retrieved 2007.
• 2、 Enoki, Makiko,Honda, Yoichi,Kuwahara, Masaaki,Watanabe, Takashi. "Chemical synthesis, iron redox interactions and charge transfer complex formation of alkylitaconic acids from Ceriporiopsis subvermispora.". . p. 9 - 20. Retrieved 2002.
• 3、 Boschert, David,Schneider-Chaabane, Alexandra,Himmelsbach, Andreas,Eickenscheidt, Alice,Lienkamp, Karen. "Synthesis and Bioactivity of Polymer-Based Synthetic Mimics of Antimicrobial Peptides (SMAMPs) Made from Asymmetrically Disubstituted Itaconates". . p. 8217 - 8227. Retrieved 2018/05/30.
• 4、 Li, Lu,Liu, Shiwei,Xu, Junming,Yu, Shitao,Liu, Fusheng,Xie, Congxia,Ge, Xiaoping,Ren, Jianyun. "Esterification of itaconic acid using Ln～SO4 2-/TiO2-SiO2 (Ln = La3+, Ce 4+, Sm3+) as catalysts". . p. 24 - 30. Retrieved 2013/04/10.