6108-58-3

Basic information

• Product Name: HEX-2-ENEDIOIC ACID DIMETHYL ESTER
• Synonyms: HEX-2-ENEDIOIC ACID DIMETHYL ESTER;2-Hexenedioic acid, 1,6-dimethyl ester;2-Hexenedioic acid, 1,6-dimethyl ester: HEX-2-ENEDIOIC ACID DIMETHYL ESTER
• CAS NO: 6108-58-3
• Molecular Formula: C₈H₁₂O₄
• Molecular Weight: 172.17848
• Mol File: 6108-58-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 388.7°C at 760 mmHg
• Flash Point: 188.9°C
• Appearance: /
• Density: 1.343g/cm³
• Vapor Pressure: 3E-06mmHg at 25°C
• Refractive Index: 1.659
• CAS DataBase Reference: HEX-2-ENEDIOIC ACID DIMETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: HEX-2-ENEDIOIC ACID DIMETHYL ESTER(6108-58-3)
• EPA Substance Registry System: HEX-2-ENEDIOIC ACID DIMETHYL ESTER(6108-58-3)

Safety Data

• Hazardous Substances Data: 6108-58-3(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 48, p. 5364, 1983 DOI: 10.1021/jo00174a043

InChI:InChI=1/C15H14Cl2N2O/c1-19(2)12-6-4-11(5-7-12)18-15(20)13-9-10(16)3-8-14(13)17/h3-9H,1-2H3,(H,18,20)

Upstream product

• 292638-85-8 acrylic acid methyl ester 
• 67-56-1 methanol 
• 261900-70-3 D-glucarate-6,3-lactone ethyl ester 
• 25126-93-6 dimethyl trans-3-hexene-1,6-dioate 
• 201230-82-2 carbon monoxide 

Downstream Products

• 105-60-2 caprolactam 

Relevant articles and documents

Hydrogen Gas-Mediated Deoxydehydration/Hydrogenation of Sugar Acids: Catalytic Conversion of Glucarates to Adipates

The development of a system for the operationally simple, scalable conversion of polyhydroxylated biomass into industrially relevant feedstock chemicals is described. This system includes a bimetallic Pd/Re catalyst in combination with hydrogen gas as a terminal reductant and enables the high-yielding reduction of sugar acids. This procedure has been applied to the synthesis of adipate esters, precursors for the production of Nylon-6,6, in excellent yield from biomass-derived sources.

Tail-to-tail dimerization of methyl acrylate in the presence of triphenylarsine ruthenium complexes

Dimerization of methyl acrylate by ruthenium-based homogenous catalysts. The effect of the addition of supporting ligands on selectivity was studied. Conversion and selectivity were significantly affected by using triphenyl arsine. Possible reaction mechanism to achieve the tail to tail product was discussed. Catalytic dimerization of methyl acrylate by homogenous ruthenium catalysts was investigated. The effect of the addition of acidic additives, supporting ligands, polymerization inhibitor, and reaction conditions on the selectivity of dimerization was studied, and possible reaction mechanism was discussed. Conversion and selectivity were significantly affected by using triphenylarsine as supporting ligand. Under mild conditions, conversion up to 98% with good selectivity to tail-to-tail product was achieved.

Ionic Liquids, 3. Synthesis and Utilisation of Protic Imidazolium Salts in Homogeneous Catalysis

Protonation of 1-alkylimidazoles provides halogen-free salts which act as ionic liquids and proton reservoir in proton- and metal-assisted catalytic processes like dimerisation of methyl acrylate and ring closing metathesis, and lead to significant improvements both in activity and selectivity.