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

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

Downstream Products

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

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.

NOVEL BISPHOSPHANE CATALYSTS

In the present Application protection is sought for compounds of the general formula (I) as ligands for reactions catalysed by transition metals. The preparation thereof and use thereof, in particular for the preparation of β-amino acids, is also discusse

Asymmetric Hydrogenation Catalyzed by (S,S)-R-BisP*-Rh and (R,R)-R-MiniPHOS Complexes: Scope, Limitations, and Mechanism

A new class of chiral C2-symmetric bis(trialkyl)phosphine ligands has been prepared and used in Rh(I)-catalyzed asymmetric hydrogenation reactions. The ligands, 1,2-bis(alkylmethylphosphino)ethanes 1 a-g (abbreviated as BisP*, alkyl = t-butyl, 1-adamantyl, 1-methylcyclohexyl, 1,1-diethylpropyl, cyclopentyl, cyclohexyl, isopropyl) and 1,2-bis(alkylmethylphosphino)methanes 2 a-d (abbreviated as MiniPHOS, alkyl = t-butyl, cyclohexyl, isopropyl, phenyl) are prepared by a simple synthetic approach based on the air-stable phosphine-boranes. These new ligands give the corresponding Rh(I) complexes, which are effective catalytic precursors for the asymmetric hydrogenation of a representative series of dehydroamino acids and itaconic acid derivatives. Enantioselectivities observed in these hydrogenations are universally high and in many cases exceed 99%. X-Ray characterization of four precatalysts, study of the pressure effects, deuteration experiments, and characterization of the wide series of intermediates in the catalytic cycle are used for the discussion of the possible correlation between the structure of the catalysts and the outcome of the catalytic asymmetric hydrogenation.