105-75-9

Basic information

• Product Name: Dibutyl fumarate
• Synonyms: Dibutyl (E)-but-2-enedioate;Fumaric acid dibutyl;Dibutyl fumarate,90%;Dibutyl fuMarate, 90% 100GR;(E)-dibutylbutenedioate;Bisomer DBF;Butyl fumarate;butylfumarate
• CAS NO: 105-75-9
• Molecular Formula: C₁₂H₂₀O₄
• Molecular Weight: 228.28
• EINECS: 203-327-9
• Product Categories: Fatty Acid Esters (Plasticizer);Functional Materials;Plasticizer
• Mol File: 105-75-9.mol
• Article Data: 21

Chemical Properties

• Melting Point: -18 °C
• Boiling Point: 141 °C (8 mmHg)
• Flash Point: 90°C
• Appearance: Clear colourless liquid
• Density: 0.98
• Vapor Pressure: 0.00388mmHg at 25°C
• Refractive Index: 1.4455-1.4475
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Insoluble in water
• Water Solubility: 11.09mg/L at 20℃
• CAS DataBase Reference: Dibutyl fumarate(CAS DataBase Reference)
• NIST Chemistry Reference: Dibutyl fumarate(105-75-9)
• EPA Substance Registry System: Dibutyl fumarate(105-75-9)

Safety Data

• Statements: 36/37/38
• Safety Statements: 24/25-36/37/39-26
• RTECS: LT1225000
• Hazardous Substances Data: 105-75-9(Hazardous Substances Data)

Usage

Description

Dibutyl fumarate is a clear, colorless liquid that serves as a versatile compound with various applications across different industries. It is a transisomer of Di-Bu maleate (DBM) and is known for its ability to enhance contact sensitization to certain substances.

Uses

Used in Plastic Industry:
Dibutyl fumarate is used as a plasticizer for industrial applications, where it helps to increase the flexibility, workability, and durability of plastics. Its addition to the manufacturing process enhances the overall performance of the final plastic product.
Used in Chemical Synthesis:
Dibutyl fumarate is used as a comonomer in the production of polystyrene, a widely used plastic material. Its incorporation into the polymerization process contributes to the development of polystyrene with specific properties tailored for various applications.
Used in Pharmaceutical Research:
As a transisomer of Di-Bu maleate (DBM), dibutyl fumarate has potential applications in pharmaceutical research, particularly in the study of contact sensitization. It has been found to enhance contact sensitization to substances like fluorescein isothiocyanate in mice, which could have implications for the development of new drugs and therapies.

Flammability and Explosibility

Nonflammable

Safety Profile

Poison by intraperitoneal route. Mildly toxic by ingestion and skin contact. An eye, skn, and mucous membrane irritant. Combustible when exposed to heat or flame; can react with oxidizing materials. To fight fire, use foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and fumes.

InChI:InChI=1/C12H20O4/c1-3-5-9-15-11(13)7-8-12(14)16-10-6-4-2/h7-8H,3-6,9-10H2,1-2H3/b8-7+

Upstream product

• 108-31-6 maleic anhydride 
• 71-36-3 butan-1-ol 
• 105-76-0 Dibutyl maleate 
• 110-17-8 (2E)-but-2-enedioic acid 
• 463-49-0 1,2-propanediene 
• 24761-88-4 1-butyl diazoacetate 
• 201230-82-2 carbon monoxide 
• 74-86-2 acetylene 
• 623-91-6 diethyl Fumarate 
• 592-84-7 n-butyl formate 
• 109-65-9 1-bromo-butane 
• 141-32-2 acrylic acid n-butyl ester 
• 1509-68-8 fumaric acid ammonium salt 
• 298-12-4 Glyoxilic acid 

Downstream Products

• 63842-87-5 butoxy-succinic acid dibutyl ester 
• 2155-60-4 di-n-butyl itaconate 
• 145039-38-9 Di-n-butyl 2-(4-Amino-3-tert-butyl-5-methylphenylthio)succinate 
• 110878-61-0 Di-n-butyl-2-(N,N-dibenzylaminoxy)succinate 
• 1380216-11-4 dibutyl 2-(3-(phenylimino)-2-oxoindolin-1-yl)-succinate 
• 1417416-02-4 dibutyl 2-(tosylamino)succinate 
• 6295-06-3 butyl glyoxalate 
• 141-03-7 dibutyl succinate 
• 2273-09-8 1,3,4-Triphenyl-4,5-dihydro-1H-1,2,4-triazol-5-one 

Relevant articles and documents

Single-Site Molybdenum Catalyst for the Synthesis of Fumarate

The catalysts with well-defined mononuclear active sites are expected to develop more active catalytic systems for the key chemical transformations. But the rational design of catalyst with stable mononuclear Mo site is still a crucial challenge because of its oligomerization tendency under reaction condition. Herein, Molybdenum catalyst (Mo-8-HQ) with single Mo sites was designed via the pyridine nitrogen and oxygen in hydroxyl of 8-hydroxyquinoline coordinated with Mo atom. The crystal catalyst was stabilized by π-π stacking interaction and hydrogen bonds to form isolated Mo specie. The single-site molybdenum catalyst exhibited excellent catalytic performance in didehydroxylation reactions with high selectively of dibutyl fumarate (86 %) product at mild reaction condition. Deuterium isotopic studies demonstrated that the mechanism feature of didehydroxylation reaction catalyzed by Mo-8-HQ was through concerted cleavage of two C?O bonds process, which could be accelerated by single-site molybdenum catalysts with electron-rich Mo centers.

Ruthenium-catalysed oxidative coupling of vinyl derivatives and application in tandem hydrogenation

The first ruthenium-catalyzed oxidative homo- and cross-coupling of exclusive vinyl derivatives giving highly valued 1,3-diene building blocks is reported. The catalytic system is based on readily available reagents and it mainly delivers the E,E isomer. This methodology also enables the synthesis of adipic acid ester derivatives in a one-pot fashion after in situ ruthenium-catalyzed hydrogenation.

POLYGLYOXYLATES, MANUFACTURE AND USE THEREOF

Self-immolative polymers degrade by an end-to-end depolymerisation mechanism in response to the cleavage of a stabilizing end-cap from the polymer terminus. Examples include homopolymers, mixed polymers including block copolymers, suitable for a variety of applications. A polyglyoxylate can be end-capped or capped with a linker as in a block copolymer.