Diethyl maleate

Base Information

• Chemical Name: Diethyl maleate
• CAS No.: 141-05-9
• Molecular Formula: C8H12O4
• Molecular Weight: 172.181
• Hs Code.: 29171990
• European Community (EC) Number: 205-451-9
• UNII: G81WQB56OL
• ChEMBL ID: CHEMBL2037000
• DSSTox Substance ID: DTXSID8020464
• Metabolomics Workbench ID: 48268
• Nikkaji Number: J5.802E
• NSC Number: 8394
• Wikidata: Q1646591
• Wikipedia: Diethyl_maleate
• Mol file: 141-05-9.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 Diethyl maleate

Chemical Property:

• Appearance/Colour: colourless liquid
• Vapor Pressure: 1 mm Hg ( 14 °C)
• Melting Point: -10 °C
• Refractive Index: n20/D 1.441(lit.)
• Boiling Point: 214 °C at 760 mmHg
• Flash Point: 93.3 °C
• PSA: 52.60000
• Density: 1.068 g/cm³
• LogP: 0.66880
• Storage Temp.: Store below +30°C.
• Solubility.: 14mg/l
• Water Solubility.: insoluble
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 172.07355886
• Heavy Atom Count: 12
• Complexity: 164

Purity/Quality:

99% ^*data from raw suppliers

Diethyl Maleate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36-43-52/53
• Safety Statements: 26-36/37-37-24-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: UVCB,Other Classes -> Esters,Other
• Canonical SMILES: CCOC(=O)C=CC(=O)OCC
• Isomeric SMILES: CCOC(=O)/C=C\C(=O)OCC
• Uses: Diethyl maleate can be used for the preparation of organophosphorus insecticide malathion. It is unsaturated polyester resins that are used in applications, such as reinforced glass fiber for boats, piping, bathtubs, roof panels, etc., and as protective coatings, finishes, and lacquers. Diethyl Maleate is used as a reagent in the synthesis of several organic compounds including that of polyaspartic acid ester based polyurea coatings. It was found to inhibit MCA and TPA transformed cell growth via modulation of glutathione, mitogen-activated protein kinase and cancer pathways.

Technology Process of Diethyl maleate

There total 314 articles about Diethyl 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: 91.0%

diazoacetic acid ethyl ester (623-73-4) + 2,5-Dimethyl-2,4-hexadiene (764-13-6) → ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate (97-41-6) + diethyl Fumarate (623-91-6) + Diethyl maleate (141-05-9)

Guidance literature:

hexarhodium hexadecacarbonyl; at 60 ℃; for 7h;

DOI:10.1016/S0040-4039(01)90438-1

Reference yield: 57.0%

diazoacetic acid ethyl ester (623-73-4) + cyclohexyl diazoacetate (63254-54-6) → ethyl cyclohexyl maleate + dicyclohexyl cis-butenedioate (621-13-6) + Diethyl maleate (141-05-9)

Guidance literature:

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; at 20 ℃;

DOI:10.1002/chem.200601692

Reference yield: 10.0%

diazoacetic acid ethyl ester (623-73-4) + cyclohexane (110-82-7,25012-93-5) → ethyl 2-cyclohexylacetate (5452-75-5) + Diethyl maleate (141-05-9)

Guidance literature:

With rhodium(II) pivalate; Heating;

DOI:10.1016/S0040-4039(98)00836-3

upstream raw materials:

Triethyl orthoacetate

maleic acid

pyridine

diethyl 2-bromosuccinate

Downstream raw materials:

1-<1,2-bis(carbethoxy)ethyl>aziridine

[(dimethoxyphosphinothioyl)thio]-butanedioic acid, diethyl ester

diphenoxythiophosphorylsulfanyl-succinic acid diethyl ester

3-Nitro-butan-1,2-dicarbonsaeure-diethylester

Refernces

• 1、 Wulfman et al.. "-". . p. 1241,1243. Retrieved 1976.
• 2、 Dzhemilev, U. M.,Fakhretdinov, R. N.,Marvanov, R. M.,Nefedov, O. M.. "REACTION OF ETHYL DIAZOACETATE WITH ALLYLAMINES CATALYZED BY COPPER AND RHODIUM COMPLEXES". . p. 539 - 543. Retrieved 1984.
• 3、 Abeykoon, Brian,Devic, Thomas,Grenèche, Jean-Marc,Fateeva, Alexandra,Sorokin, Alexander B.. "Confinement of Fe-Al-PMOF catalytic sites favours the formation of pyrazoline from ethyl diazoacetate with an unusual sharp increase of selectivity upon recycling". . p. 10308 - 10311. Retrieved 2018.
• 4、 Sato et al.. "-". . p. 1833. Retrieved 1973.
• 5、 Simkhovich, Liliya,Mahammed, Atif,Goldberg, Israel,Gross, Zeev. "Synthesis and Characterization of Germanium, Tin, Phosphorus, Iron, and Rhodium Complexes of Tris(pentafluorophenyl)corrole, and the Utilization of the Iron and Rhodium Corroles as Cyclopropanation Catalysts". . p. 1041 - 1055. Retrieved 2001.
• 6、 Dragutan, Ileana,Dragutan, Valerian,Verpoort, Francis. "Carbenoid transfer in competing reactions catalyzed by ruthenium complexes". . p. 211 - 215. Retrieved 2014.
• 7、 Bertani, Roberta,Biasiolo, Monica,Darini, Katia,Michelin, Rino A,Mozzon, Mirto,Visentin, Fabiano,Zanotto, Livio. "Catalytic transformations of diazo compounds promoted by platinum(0) and dicationic platinum(II) complexes". . p. 32 - 39. Retrieved 2002.
• 8、 Castano, Brunilde,Gallo, Emma,Cole-Hamilton, David J.,Dal Santo, Vladimiro,Psaro, Rinaldo,Caselli, Alessandro. "Continuous flow asymmetric cyclopropanation reactions using Cu(i) complexes of Pc-L* ligands supported on silica as catalysts with carbon dioxide as a carrier". . p. 3202 - 3209. Retrieved 2014.
• 9、 Demerseman, Bernard,Dixneuf, Pierre H.. "Hydrogenation of Alkynes with Water and a Titanium(II) Complex". . p. 665 - 666. Retrieved 1981.
• 10、 Hetterscheid, Dennis G. H.,Hendriksen, Coen,Dzik, Wojciech I.,Smits, Jan M. M.,Van Eck, Ernst R. H.,Rowan, Alan E.,Busico, Vincenzo,Vacatello, Michele,Van Axel Castelli, Valeria,Segre, Annalaura,Jellema, Erica,Bloemberg, Tom G.,De Bruin, Bas. "Rhodium-mediated stereoselective polymerization of "carbenes"". . p. 9746 - 9752. Retrieved 2006.