Diethyl fumarate

Base Information

• Chemical Name: Diethyl fumarate
• CAS No.: 623-91-6
• Molecular Formula: C8H12O4
• Molecular Weight: 172.181
• Hs Code.: 29171990
• European Community (EC) Number: 210-819-7
• NSC Number: 20954
• UNII: 5WBU5A3E8A
• DSSTox Substance ID: DTXSID7027253
• Nikkaji Number: J43.455H,J520.492E
• Wikidata: Q27159582
• Metabolomics Workbench ID: 130683
• ChEMBL ID: CHEMBL3187857
• Mol file: 623-91-6.mol

Synonyms:diethyl fumarate;fumaric acid, diethyl ester

Chemical Property of Diethyl fumarate

Chemical Property:

• Appearance/Colour: colourless liquid
• Vapor Pressure: 0.159mmHg at 25°C
• Melting Point: 1-2 °C(lit.)
• Refractive Index: n20/D 1.44(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.: 3.1g/l
• Water Solubility.: immiscible
• 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 fumarate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Esters, Other
• Canonical SMILES: CCOC(=O)C=CC(=O)OCC
• Isomeric SMILES: CCOC(=O)/C=C/C(=O)OCC
• Uses: It is used as a pesticide or comonomer for the production of polystyrene. Diethyl fumarate is unsaturated polyester resins are used in applications, such as reinforced glass fiber for boats, piping, bathtubs, roof panels, etc., and as protective coatings, finishes, and lacquers. Diethyl Fumarate is a reagent in the preparation of chiral hydroisoindolines via Diels-Alder cycloaddition which are potent, brain-penetrant, human neurokinin-1 receptor antagonists.

Technology Process of Diethyl fumarate

There total 280 articles about Diethyl fumarate 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%

diethyl meso-2,3-dibromosuccinate (1114-31-4) → diethyl Fumarate (623-91-6)

Guidance literature:

With N-benzyl-1,4-dihydronicotinamide; In acetonitrile; at 49.9 ℃; for 2h;

DOI:10.1246/bcsj.58.1847

Reference yield: 93.0%

diazoacetic acid ethyl ester (623-73-4) → diethyl Fumarate (623-91-6)

Guidance literature:

With 2-(di-tert-butylphosphino)-1,1'-biphenylgold(I) chloride; silver(I) triflimide; 1-(dimethoxymethyl)-2-ethynylbenzene; In dichloromethane; at 28 ℃; for 18h; Inert atmosphere;

DOI:10.1002/anie.201303016

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

upstream raw materials:

diazoacetic acid ethyl ester

Diethyl maleate

sodium diethylmalonate

diethyl meso-2,3-dibromosuccinate

Downstream raw materials:

trans-1,2-bis(ethoxycarbonyl)-4-cyclohexene

diethyl 2-ethylidenesuccinate

diethyl isopropylidenesuccinate

diethyl 2-(diethoxyphosphoryl)succinate

Refernces

• 1、 Liu, Michael T. H.,Doyle, Michael P.,Loh, Kuo-Liang,Anand, Surinder M.. "Catalysis of Olefin Isomerization by Tight Ion Pairs". . p. 323 - 324. Retrieved 1987.
• 2、 Bradsher,Stone. "-". . p. 519. Retrieved 1968.
• 3、 Torikai et al.. "-". . p. 339. Retrieved 1975.
• 4、 Tsuji,Nogi. "-". . p. 2641. Retrieved 1966.
• 5、 Cai, Zhenping,Chen, Rujia,Jiang, Lilong,Li, Fukun,Li, Xuehui,Long, Jinxing,Zhang, Hao. "One-pot production of diethyl maleate via catalytic conversion of raw lignocellulosic biomass". supporting information. p. 10116 - 10122. Retrieved 2021/12/24.
• 6、 Cheng, Shun-Cheung,Cheung, Wai-Man,Chong, Man-Chun,Ko, Chi-Chiu,Leung, Wa-Hung,Sung, Herman H.-Y.,Williams, Ian D.. "Synthesis, structure and reactivity of iridium complexes containing a bis-cyclometalated tridentate C^N^C ligand". . p. 8512 - 8523. Retrieved 2021/06/28.