ITACONIC ACID MONOMETHYL ESTER

Base Information

• Chemical Name: ITACONIC ACID MONOMETHYL ESTER
• CAS No.: 7338-27-4
• Molecular Formula: C6H8O4
• Molecular Weight: 144.127
• Hs Code.: 2917198090
• European Community (EC) Number: 230-853-6
• NSC Number: 144957
• UNII: 2EJ2DV6SCJ
• DSSTox Substance ID: DTXSID20223618
• Nikkaji Number: J121.434I
• Wikidata: Q83102080
• Mol file: 7338-27-4.mol

Synonyms:4-methoxy-2-methylidene-4-oxo-butanoic acid;4-methoxy-2-methylidene-4-oxobutanoic acid;4-Methyl itaconate;Butanedioic acid, methylene-, 4-methyl ester;Monomethyl Itaconate;beta-Methyl Itaconate;4-Methyl Methylenesuccinate;Itaconic Acid Monomethyl Ester;

Chemical Property of ITACONIC ACID MONOMETHYL ESTER

Chemical Property:

• Vapor Pressure: 0.000663mmHg at 25°C
• Melting Point: 72°C
• Refractive Index: 1.455
• Boiling Point: 149 °C / 10mmHg
• PKA: 3.59±0.10(Predicted)
• Flash Point: 122.1°C
• PSA: 63.60000
• Density: 1.195g/cm³
• LogP: 0.19030
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: soluble in Methanol
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 144.04225873
• Heavy Atom Count: 10
• Complexity: 171

Purity/Quality:

98%,99%, ^*data from raw suppliers

ItaconicAcidMonomethylEster ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

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

Technology Process of ITACONIC ACID MONOMETHYL ESTER

There total 6 articles about ITACONIC ACID MONOMETHYL ESTER 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: 99.0%

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

Guidance literature:

toluene-4-sulfonamide; at 40 ℃; for 48h;

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:

methanol (67-56-1) + itaconic acid anhydride (2170-03-8) → 4-methoxy-2-methylene-4-oxobutanoic acid (7338-27-4) + Dimethyl itakonate (617-52-7)

Guidance literature:

With sulfuric acid; In dichloromethane; at 20 ℃;

DOI:10.1002/chem.201800907

upstream raw materials:

methanol

2-methylenesuccinic acid

itaconic acid anhydride

Downstream raw materials:

1-benzyl-4-methyl itaconate

3-[benzyl(2-iodophenyl)carbamoyl]but-3-enoic acid methyl ester

2-(2-azidoethyl)-N-benzyl-N-(2-iodophenyl)acrylamide

N-benzyl-4-hydroxy-N-(2-iodophenyl)-2-methylenebutanamide

Refernces

• 1、 Garnsey, Michelle R.,Slutskyy, Yuriy,Jamison, Christopher R.,Zhao, Peng,Lee, Juyeol,Rhee, Young Ho,Overman, Larry E.. "Short Enantioselective Total Syntheses of Cheloviolenes A and B and Dendrillolide C via Convergent Fragment Coupling Using a Tertiary Carbon Radical". . p. 6958 - 6976. Retrieved 2018.
• 2、 Ju, An-Qi,Li, Meng-Juan,Luo, Miao,Ge, Ming-Qiao. "Poly(acrylonitrile-co-3-aminocarbonyl-3-butenoic acid methyl ester): A better precursor material for carbon fiber than acrylonitrile terpolymer". . p. 1275 - 1278. Retrieved 2014.
• 3、 Hornink, Milene Macedo,Lopes, Alice Uva,Andrade, Leandro Helgueira. "Biobased Spiroimides from Itaconic Acid and Formamides: Molecular Targets for a Novel Synthetic Application of Renewable Chemicals". supporting information. p. 296 - 308. Retrieved 2020/11/09.
• 4、 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.