Monoethyl maleate

Base Information

• Chemical Name: Monoethyl maleate
• CAS No.: 3990-03-2
• Deprecated CAS: 144472-88-8
• Molecular Formula: C₆H₈O₄
• Molecular Weight: 144.127
• European Community (EC) Number: 273-500-1,223-635-7
• NSC Number: 525207,524101,11206
• UNII: AK5N1DQX7U
• DSSTox Substance ID: DTXSID60892145
• Nikkaji Number: J114.854K
• Wikidata: Q27273964
• Metabolomics Workbench ID: 48905
• Mol file: 3990-03-2.mol

Synonyms:diethyl maleate;diethyl maleic acid diester;diethylmaleate;ethyl hydrogen maleate;ethyl maleate;maleic acid diethyl ester;maleic acid, ethyl ester;monoethyl maleate

Chemical Property of Monoethyl maleate

Chemical Property:

• Refractive Index: 1.4570 to 1.4600
• Boiling Point: 261.6 °C at 760 mmHg
• PKA: 2.69±0.25(Predicted)
• Flash Point: 109.6°C
• PSA: 63.60000
• Density: 1.208 g/cm³
• LogP: 0.19030
• Storage Temp.: Refrigerator
• Solubility.: Chloroform, Ethyl Acetate
• 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: 159

Purity/Quality:

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

(2Z)-2-ButenedioicAcid1-EthylEster,~90% ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: UVCB
• Canonical SMILES: CCOC(=O)C=CC(=O)O
• Isomeric SMILES: CCOC(=O)/C=C\C(=O)O
• Uses: (2Z)-2-Butenedioic Acid 1-Ethyl Ester is a phytochemical isolated from cranberries. (2Z)-2-Butenedioic Acid 1-Ethyl Ester was shown to exhibit potential antiproliferative and antioxidant activities.

Technology Process of Monoethyl maleate

There total 6 articles about Monoethyl 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: 99.0%

maleic anhydride (108-31-6) + ethanol (64-17-5) → malonic acid monoethyl ester (2459-05-4,3249-53-4,3990-03-2)

Guidance literature:

at 60 ℃; for 2h; regioselective reaction;

DOI:10.1021/ol302069h

Reference yield: 94.0%

succinic acid anhydride (108-30-5) + ethanol (64-17-5) → malonic acid monoethyl ester (2459-05-4,3249-53-4,3990-03-2)

Guidance literature:

Heating;

DOI:10.1039/c8ra06354k

Reference yield: 33.0%

diazoacetic acid ethyl ester (623-73-4) + ethyl 2-diazo-3-methyl-3-butenoate (126580-11-8) → malonic acid monoethyl ester (2459-05-4,3249-53-4,3990-03-2) + (E)-4-ethoxy-4-oxobut-2-enoic acid (2459-05-4) + diethyl 2-methylcyclobutene-1,3-dicarboxylate (1198173-63-5)

Guidance literature:

With tetrakis(acetonitrile)copper(I)tetrafluoroborate; In dichloromethane; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1002/anie.200903902

upstream raw materials:

maleic anhydride

ethanol

ethyl iodide

diethyl ether

Downstream raw materials:

maleic anhydride

(Z)-But-2-enedioic acid ethyl ester 2,4,4-trimethyl-3-vinyl-cyclohex-2-enyl ester

(Z)-But-2-enedioic acid 3-benzo[d]imidazo[2,1-b]thiazol-2-yl-phenyl ester ethyl ester

fumaric acid ethyl ester mono chloride

Refernces

• 1、 -. "DRUGS AND COMPOSITIONS FOR THE TREATMENT OF OCULAR DISORDERS". Page/Page column 245; 383. . Retrieved 2018/10/19.
• 2、 Bonneaud, Céline,Decostanzi, Mélanie,Burgess, Julia,Trusiano, Giuseppe,Burgess, Trevor,Bongiovanni, Roberta,Joly-Duhamel, Christine,Friesen, Chadron M.. "Synthesis of α,β-unsaturated esters of perfluoropolyalkylethers (PFPAEs) based on hexafluoropropylene oxide units for photopolymerization". . p. 32664 - 32671. Retrieved 2018/10/15.