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

Occurrence

Has apparently not been reported to occur in nature.

Uses

Dimethyl Citraconate is a useful synthetic intermediate. It has been used in the synthesis of natural products chaetomellic acid A anhydride and 1,7(Z)- nonadecadiene-2,3-dicarboxylic acid. It is also used to prepare acyclic alkanes by reduction using homogeneous catalysts or biocatalysts.

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 
• 917-54-4 methyllithium 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 186581-53-3 diazomethane 
• 498-24-8 Mesaconic acid 
• 21307-96-0 methyl 2-methylsuccinate 
• 75-16-1 methylmagnesium bromide 
• 74-88-4 methyl iodide 

Downstream Products

• 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 
• 1604-11-1 (S)-dimethyl 2-methylsuccinate 
• 5754-18-7 4-methyl-1,2-dihydropyridazine-3,6-dione 
• 83005-08-7 2-amino-2-methyl-succinamic acid 
• 498-23-7 citraconic acid 
• 71028-76-7 2-methyl-but-2-enedioic acid 1-methyl ester 
• 3641-51-8 2-(R)-methylsuccinic acid 

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 convenient procedure for bis-esterification of cyclic anhydrides

Aromatic and aliphatic cyclic anhydrides are chemoselectively and conveniently transformed to the corresponding diesters by the use of DBU and appropriate alkyl/allyl halides. This bis-esterification reaction has been exemplified mostly with dimethyl esters. But in some cases, mixed dialkyl esters are also prepared.