Dimethyl maleate

Base Information

• Chemical Name: Dimethyl maleate
• CAS No.: 624-48-6
• Molecular Formula: C6H8O4
• Molecular Weight: 144.127
• Hs Code.: 2917.19
• European Community (EC) Number: 210-848-5
• UNII: K39366X5N0
• ChEMBL ID: CHEMBL2259700
• DSSTox Substance ID: DTXSID4040765
• Nikkaji Number: J45.018I
• NSC Number: 5161
• Wikidata: Q2377169
• Wikipedia: Dimethyl_maleate
• Mol file: 624-48-6.mol

Synonyms:dimethyl maleate;maleic acid, dimethyl ester

Chemical Property of Dimethyl maleate

Chemical Property:

• Appearance/Colour: colourless liquid
• Vapor Pressure: 0.475mmHg at 25°C
• Melting Point: -19 °C
• Refractive Index: 1.442 - 1.443
• Boiling Point: 193 °C at 760 mmHg
• Flash Point: 91.1 °C
• PSA: 52.60000
• Density: 1.124 g/cm³
• LogP: -0.11140
• Storage Temp.: Store below +30°C.
• Solubility.: water: soluble77.9g/L at 20°C
• Water Solubility.: Miscible with water.
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 144.04225873
• Heavy Atom Count: 10
• Complexity: 141

Purity/Quality:

99% ^*data from raw suppliers

Dimethyl maleate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,C
• Statements: 21/22-36/37/38-43-37-34-22
• Safety Statements: 26-36/37-23-45-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Esters, Other
• Canonical SMILES: COC(=O)C=CC(=O)OC
• Isomeric SMILES: COC(=O)/C=C\C(=O)OC
• Uses: Dimethyl maleate is widely used in the plastics and chemical industries and as a vaporization retardant of insecticides. Dimethyl maleate is acts as a dienophile involved in ultrasonic irradiation promoted Diels-Alder reaction with substituted furans. It is widely used as an intermediate and additive for pharmaceuticals, copolymers, pigments, plastics, paints, adhesives and agrochemicals. As an internal modifier, it increases the glass transition temperature of styrene or vinyl chloride polymer. It plays a vital role to improve the hardness and toughness of polymer films such as copolymers of vinyl acetate.

Technology Process of Dimethyl maleate

There total 127 articles about Dimethyl maleate 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%

methanol (67-56-1) + maleic acid (110-16-7,26099-09-2) → dimethyl cis-but-2-ene-1,4-dioate (624-48-6)

Guidance literature:

With boron trifluoride; at 65 ℃; for 0.333333h;

DOI:10.1021/ac049919h

Reference yield: 98.0%

dimethyl acetylenedicarboxylate (762-42-5) → dimethyl cis-but-2-ene-1,4-dioate (624-48-6)

Guidance literature:

With hydrogen; montmorillonit-bipyridinpalladium(II)-acetate; In tetrahydrofuran; Ambient temperature;

Reference yield: 95.0%

maleic anhydride (108-31-6) + tert-butyl methyl ether (1634-04-4) → dimethyl cis-but-2-ene-1,4-dioate (624-48-6)

Guidance literature:

With sulfuric acid; at 10 - 20 ℃; regioselective reaction;

DOI:10.1016/j.tetlet.2011.04.100

upstream raw materials:

methyl diazoacetate

maleic anhydride

methanol

dimethyl 2-bromosuccinate

Downstream raw materials:

4-methoxycarbonyl-pyrazoline-3-carboxylic acid methyl ester

Z-dimethyl 3-phenyl-4,5-dihydroisoxazole-4,5-dicarboxylate

dimethyl 2-acetylsuccinate

4H-spiro[pyrazole-3,9'-thioxanthene]-4,5-dicarboxylic acid dimethyl ester

Refernces

• 1、 Molchanov,Stepakov,Kopf,Zenkevich,Kostikov. "Reactions of methoxycarbonylcarbene with 3-ethyl-2-phenyl- and 2,3-diphenyloxazolidines". . p. 2144 - 2148. Retrieved 2001.
• 2、 Holden, David A.,Gray, J. Bradley,McEwan, Ian. "Bichromophoric Compounds. Photophysics and Photochemistry of (1-Naphthyl)alkyl Esters of Fumaric, Maleic, and Oxalic Acids". . p. 866 - 873. Retrieved 1985.
• 3、 Lemal, David M.,Sang, Dayong,Ramanathan, Sudharsanam. "o-Fluoranil: Stereochemistry and mechanism of its Diels-Alder reactions". . p. 7804 - 7811. Retrieved 2009.
• 4、 -. "Method for preparing diacid diester compound under catalysis of deep eutectic solvent". Paragraph 0055-0058. . Retrieved 2021/05/19.
• 5、 -. "Method for preparing maleate by catalyzing maleic anhydride with ionic liquid". Paragraph 0025; 0030; 0031; 0036. . Retrieved 2020/02/29.