Dibutyl fumarate

Base Information

• Chemical Name: Dibutyl fumarate
• CAS No.: 105-75-9
• Deprecated CAS: 72399-98-5,76736-49-7,76736-49-7
• Molecular Formula: C12H20O4
• Molecular Weight: 228.288
• Hs Code.: 29171900
• European Community (EC) Number: 203-327-9
• UNII: CQM31Z1NU9
• ChEMBL ID: CHEMBL3247950
• DSSTox Substance ID: DTXSID7021865
• Nikkaji Number: J47.522J,J520.498D
• NSC Number: 165581,140
• Wikidata: Q27275660
• Mol file: 105-75-9.mol

Synonyms:2-Butenedioicacid (2E)-, dibutyl ester (9CI);2-Butenedioic acid (E)-, dibutyl ester;Fumaric acid, dibutyl ester (6CI,8CI);Butyl fumarate;Fumaric acid di-n-butyl ester;NSC 140;RC Comonomer DBF;Staflex DBF;

Chemical Property of Dibutyl fumarate

Chemical Property:

• Appearance/Colour: Clear colourless liquid
• Vapor Pressure: 0.00388mmHg at 25°C
• Melting Point: -18 °C
• Refractive Index: 1.4455-1.4475
• Boiling Point: 280 °C at 760 mmHg
• Flash Point: 136.4 °C
• PSA: 52.60000
• Density: 1.004 g/cm³
• LogP: 2.22920
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Insoluble in water
• Water Solubility.: 11.09mg/L at 20℃
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 10
• Exact Mass: 228.13615911
• Heavy Atom Count: 16
• Complexity: 209

Purity/Quality:

99% ^*data from raw suppliers

Dibutyl Fumarate ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 24/25-36/37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Esters, Other
• Canonical SMILES: CCCCOC(=O)C=CC(=O)OCCCC
• Isomeric SMILES: CCCCOC(=O)/C=C/C(=O)OCCCC
• Uses: Dibutyl fumarate is used as a comonomer for the production of polystyrene. Dibutyl Fumarate is a transisomer of Di-Bu maleate (DBM), which is widely used as a plasticizer for industrial application and enhances contact sensitization to fluorescein isothiocyanate in mice.

Technology Process of Dibutyl fumarate

There total 22 articles about Dibutyl 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: 98.0%

maleic anhydride (108-31-6) + butan-1-ol (71-36-3) → dibutyl fumarate (105-75-9,29014-71-9)

Guidance literature:

With sulfuric acid; acetonitrile; at 80 - 85 ℃; for 16 - 18h;

DOI:10.1080/00397911.2013.837485

Reference yield: 94.0%

(2E)-but-2-enedioic acid (110-17-8,26099-09-2) + butan-1-ol (71-36-3) → dibutyl fumarate (105-75-9,29014-71-9)

Guidance literature:

With sulfuric acid; at 120 ℃; for 16h;

DOI:10.1021/ja504727u

Reference yield: 91.0%

acrylic acid n-butyl ester (141-32-2,9003-49-0) → dibutyl fumarate (105-75-9,29014-71-9)

Guidance literature:

polyethylene glycol bound Hoveyda-Grubbs Ru catalyst; In dichloromethane; for 6h; Heating;

DOI:10.1016/j.tetlet.2004.01.036

upstream raw materials:

maleic anhydride

butan-1-ol

Dibutyl maleate

(2E)-but-2-enedioic acid

Downstream raw materials:

butoxy-succinic acid dibutyl ester

di-n-butyl itaconate

Di-n-butyl-2-(N,N-dibenzylaminoxy)succinate

Refernces

• 1、 Pal, Bikash,Lin, Bo-Chao,Dela Cerna, Mark Vincent Carreon,Hsu, Chao-Ping,Lin, Chih-Hsiu. "Face-to-Face Packing of 2,3,9,10-Tetrasubstituted Pentacene Derivatives Revealed through a Solid State [4 + 4] Thermal Cycloaddition and Molecular Dynamic Simulation". . p. 6223 - 6234. Retrieved 2016.
• 2、 -. "Method for preparing succinate by double carbonylation of acetylene". Paragraph 0027-0038. . Retrieved 2019/12/02.