111266-16-1

Basic information

• Product Name: (S)-2-METHYLSUCCINIC ACID 1-METHYL ESTER
• Synonyms: (S)-2-METHYLSUCCINIC ACID 1-METHYL ESTER;(S)-4-methoxy-3-methyl-4-oxobutanoic acid
• CAS NO: 111266-16-1
• Molecular Formula: C₆H₁₀O₄
• Molecular Weight: 146.1412
• Mol File: 111266-16-1.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 248.8±23.0 °C(Predicted)
• Appearance: /
• Density: 1.159±0.06 g/cm3(Predicted)
• PKA: 4.44±0.19(Predicted)
• CAS DataBase Reference: (S)-2-METHYLSUCCINIC ACID 1-METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-METHYLSUCCINIC ACID 1-METHYL ESTER(111266-16-1)
• EPA Substance Registry System: (S)-2-METHYLSUCCINIC ACID 1-METHYL ESTER(111266-16-1)

Safety Data

• Hazardous Substances Data: 111266-16-1(Hazardous Substances Data)

Usage

General Description

(S)-2-Methylsuccinic acid 1-methyl ester is a chemical compound with the molecular formula C6H10O4. It is an ester of (S)-2-methylsuccinic acid, which is a naturally occurring compound found in a variety of fruits and vegetables. This chemical is primarily used in the pharmaceutical and research industries as a building block for the synthesis of various compounds. It is also used in the production of fragrances and flavors. In addition, (S)-2-Methylsuccinic acid 1-methyl ester has potential applications in agriculture and as a chiral auxiliary in organic synthesis. It is a colorless to pale yellow liquid with a fruity odor and is considered to be relatively stable under normal conditions.

Upstream product

• 3377-31-9 methyl itaconate 
• 1604-11-1 (S)-dimethyl 2-methylsuccinate 
• 67-56-1 methanol 
• 4100-80-5 2-methylsuccinic anhydride 
• 21307-96-0 methyl 2-methylsuccinate 
• 71-23-8 propan-1-ol 
• 32980-25-9 2-methylsuccinic acid 1-methyl ester 
• 20459-96-5 methyl (S)-2-methylpent-4-enoate 

Downstream Products

• 4454-18-6 (S,S)-2,5-dimethyl-adipic acid 
• 19550-58-4 (R,R)-2,5-dimethyl-adipic acid dimethyl ester 
• 1604-11-1 (S)-dimethyl 2-methylsuccinate 

Relevant articles and documents

Highly enantioselective rhodium-catalyzed hydrogenation of 2-(2-methoxy-2-oxoethyl)acrylic acid - A convenient access of enantiomerically pure isoprenoid building blocks

Asymmetric catalytic hydrogenation of 2-(2-methoxy-2-oxoethyl)acrylic acid (5) to give (2S)-4-methoxy-2-methyl-4-oxobutanoic acid [(S)-6] was studied. An enantiomeric excess of 99.7% ee was achieved with a catalyst formed in situ from [Rh(COD)2]BF4 and the chiral phosphite L2 in 1,2-dichloroethane as solvent. In addition, enzyme-catalyzed semi-saponification of dimethyl 2-methylsuccinate was investigated. Mono ester (S)-6 was transformed into a few compounds which can serve as C 5-building blocks in natural product syntheses. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

Expanding the scope of atropisomeric monodentate P-donor ligands in asymmetric catalysis: Hydrogen-transfer reduction of α,β-unsaturated acid derivatives by rhodium/Ph-binepine catalysts

A range of α,β-unsaturated acids and esters have been selectively reduced to the corresponding saturated acid derivatives by hydrogen transfer. As the reducing agent, formic acid was used in the presence of Rh 1 complexes formed with the powerful chiral ligand Ph-binepine (1), an axially chiral binaphthalene-type monodentate P-donor ligand. Very high stereoselectivities (up to 97% ee) were obtained in the case of itaconic acid (2a).

Parallel kinetic resolutions of monosubstituted succinic anhydrides catalyzed by a modified cinchona alkaloid [7]

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