617-54-9

Basic information

• Product Name: CITRACONIC ACID DIMETHYL ESTER
• Synonyms: 2-Butenedioic acid, 2-methyl-, dimethyl ester (Z)-;2-methyl-,dimethylester,(z)-2-butenedioicaci;2-Methyl-but-2-enedioic acid dimethyl ester, Z;cis-2-methyl-2-butenedioicacid,dimethylester;cis-2-methyl-but-2-enoicaciddimethylester;Dimethyl (2Z)-2-methyl-2-butenedioate;Dimethyl methyl maleate;dimethylmethylmaleate
• CAS NO: 617-54-9
• Molecular Formula: C₇H₁₀O₄
• Molecular Weight: 158.15
• Mol File: 617-54-9.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 211 °C
• Appearance: /
• Density: 1,11 g/cm3
• Refractive Index: 1.4460-1.4490
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: CITRACONIC ACID DIMETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: CITRACONIC ACID DIMETHYL ESTER(617-54-9)
• EPA Substance Registry System: CITRACONIC ACID DIMETHYL ESTER(617-54-9)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36
• RTECS: GE6700000
• Hazardous Substances Data: 617-54-9(Hazardous Substances Data)

Usage

Description

Citraconic Acid Dimethyl Ester, also known as Dimethyl Citraconate, is an organic compound that serves as a valuable synthetic intermediate in the chemical industry. It is characterized by its ester functional group and is derived from citraconic acid. CITRACONIC ACID DIMETHYL ESTER is not found in nature and is synthesized for various applications due to its unique chemical properties.

Uses

Used in Chemical Synthesis:
Citraconic Acid Dimethyl Ester is used as a synthetic intermediate for the production of various natural products. It plays a crucial role in the synthesis of chaetomellic acid A anhydride and 1,7(Z)-nonadecadiene-2,3-dicarboxylic acid, which are important compounds in the pharmaceutical and chemical industries.
Used in the Preparation of Acyclic Alkanes:
Citraconic Acid Dimethyl Ester is also utilized in the preparation of acyclic alkanes through reduction reactions. This process can be carried out using homogeneous catalysts or biocatalysts, making it a versatile compound for the production of alkanes, which are essential components in various chemical and industrial applications.

Preparation

By the reaction of methanol with citraconic anhydride in the presence of a catalyst.

Synthesis Reference(s)

Journal of the American Chemical Society, 94, p. 9269, 1972 DOI: 10.1021/ja00781a071

Upstream product

• 67-56-1 methanol 
• 498-23-7 citraconic acid 
• 616-02-4 citraconic acid anhydride 
• 186581-53-3 diazomethane 
• 498-24-8 Mesaconic acid 
• 74-88-4 methyl iodide 
• 21307-96-0 methyl 2-methylsuccinate 
• 75-16-1 methylmagnesium bromide 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 917-54-4 methyllithium 

Downstream Products

• 40704-11-8 3-methyl-1H-pyrazole-4-carboxylic acid 
• 25306-99-4 dimethyl 2-(methoxymethyl)succinate 
• 99-14-9 tricarallylic acid 
• 85460-74-8 di(2,3,6-trimethyl-4-hydroxyphenyl) disulfide 
• 107697-36-9 2-(4-Hydroxy-2,3,5-trimethyl-phenylsulfanyl)-2-methyl-succinic acid dimethyl ester 
• 129625-11-2 2-Isoquinolin-1-yl-3-methyl-5-phenyl-3H-pyrrole-3,4-dicarboxylic acid dimethyl ester 
• 129625-09-8 5-(1-isoquinoleinyl)-3-methyl-5-hydroxy-5-phenyl-4,5-dihydro-3H-pyrrole-cis-3,4-dicarboxylate de dimethyle 
• 100857-82-7 dimethyl 2-methyl-2,3-dibromosuccinate, d,l-threo isomer 
• 22644-27-5 (R)-methylsuccinic acid dimethyl ester 
• 498-23-7 citraconic acid 
• 71028-76-7 2-methyl-but-2-enedioic acid 1-methyl ester 
• 3641-51-8 2-(R)-methylsuccinic acid 
• 83509-04-0 (R)-2-methylsuccinate-1-monomethyl ester 
• 23268-03-3 (R)-2-methyl-succinic acid 4-methyl ester 

Relevant articles and documents

A Br?nsted acidic, ionic liquid containing, heteropolyacid functionalized polysiloxane network as a highly selective catalyst for the esterification of dicarboxylic acids

A Br?nsted acidic, ionic liquid containing, heteropolyanion functionalized polysiloxane network was formed by self-condensation of dodecatungstophosphoric acid and a zwitterionic organosilane precursor containing both imidazolinium and sulfonate groups. The resulting hybrid material POS-HPA-IL was investigated as a catalyst for the selective esterification of dicarboxylic acids.

Asymmetric hydrogenation of maleic acid diesters and anhydrides

Asymmetric hydrogenation of maleic and fumaric acid derivatives with iridium catalysts based on N,P ligands provides an efficient route to chiral enantioenriched succinates. A new catalyst derived from a 2,6-difluorophenyl- substituted pyridine-phosphinite ligand was developed and enables the conversion of a wide range of 2-alkyl and 2-arylmaleic acid diesters into the corresponding succinates in high enantiomeric purity. Mixtures of cis/trans substrates can be hydrogenated in an enantioconvergent fashion with high enantioselectivity, and further enhances the scope of this transformation. The products are valuable chiral building blocks with a structural motif found in many bioactive compounds, such as metalloproteinase inhibitors. An attractive enantioselective route to 2-alkyl- and 2-aryl-substituted succinic acid derivatives is opened up by the asymmetric hydrogenation of maleic and fumaric acid derivatives, using the new catalyst [Ir(cod)L]BArF, derived from a 2,6-difluorophenyl-substituted pyridine-phosphinite ligand. The products are valuable chiral building blocks having a structural motif found in many bioactive compounds. cod=1,5-cyclooctadiene.

A three-enzyme system involving an ene-reductase for generating valuable chiral building blocks

The use of ene-reductase (ERED) enzymes for the asymmetric reduction of olefins offers a green, renewable alternative to metal-catalysed asymmetric reduction. We report herein the first example of an ERED-catalysed enantiospecific reduction carried out at large scale using a carbonyl reductase (CRED) enzyme in the cofactor recycle. This reaction has been paired with a hydrolase-mediated regioselective ester hydrolysis to generate a valuable chiral building block using a straightforward one-pot process. Copyright