111197-93-4

Basic information

• Product Name: methyl (S)-2-(4-methylphenyl)propionate
• Synonyms: methyl (S)-2-(4-methylphenyl)propionate
• CAS NO: 111197-93-4
• Molecular Weight: 178.231
• Mol File: 111197-93-4.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: methyl (S)-2-(4-methylphenyl)propionate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (S)-2-(4-methylphenyl)propionate(111197-93-4)
• EPA Substance Registry System: methyl (S)-2-(4-methylphenyl)propionate(111197-93-4)

Safety Data

• Hazardous Substances Data: 111197-93-4(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 124709-72-4 (S)-(+)-2-(4'-methylphenyl)propanoic acid 
• 938-94-3 (R,S)-2-(4'-methylphenyl) propionic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 201230-82-2 carbon monoxide 
• 186581-53-3 diazomethane 
• 79443-97-3 methyl 2-(4-methylphenyl)propanoate 
• 5337-93-9 4'-methylpropiophenone 
• 108-88-3 toluene 
• 105457-91-8 2-oxo-2-(p-tolyl)acetyl chloride 
• 1429641-13-3 2-(p-tolyl)acryloyl chloride 
• 66616-85-1 α-(4-methylphenyl)acrylic acid 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 93922-51-1 (S)-2-(4-methylphenyl)-1-propanol 

Relevant articles and documents

Palladium-Catalyzed Asymmetric Markovnikov Hydroxycarbonylation and Hydroalkoxycarbonylation of Vinyl Arenes: Synthesis of 2-Arylpropanoic Acids

Asymmetric hydroxycarbonylation is one of the most fundamental yet challenging methods for the synthesis of carboxylic acids. Herein, we reported the development of a palladium-catalyzed highly enantioselective Markovnikov hydroxycarbonylation of vinyl arenes with CO and water. A monodentate phosphoramidite ligand L6 plays vital role in the reaction. The reaction tolerates a range of functional groups, and provides a facile and atom-economical approach to an array of 2-arylpropanoic acids including several commonly used non-steroidal anti-inflammatory drugs. The catalytic system has also enabled an asymmetric Markovnikov hydroalkoxycarbonylation of vinyl arenes with alcohols to afford 2-arylpropanates. Mechanistic investigations suggested that the hydropalladation is irreversible and is the regio- and enantiodetermining step, while hydrolysis/alcoholysis is probably the rate-limiting step.

Asymmetric Hydrogenation of α-Substituted Acrylic Acids Catalyzed by a Ruthenocenyl Phosphino-oxazoline-Ruthenium Complex

Asymmetric hydrogenation of various α-substituted acrylic acids was carried out using RuPHOX-Ru as a chiral catalyst under 5 bar H2, affording the corresponding chiral α-substituted propanic acids in up to 99% yield and 99.9% ee. The reaction could be performed on a gram-scale with a relatively low catalyst loading (up to 5000 S/C), and the resulting product (97%, 99.3% ee) can be used as a key intermediate to construct bioactive chiral molecules. The asymmetric protocol was successfully applied to an asymmetric synthesis of dihydroartemisinic acid, a key intermediate required for the industrial synthesis of the antimalarial drug artemisinin.

Rational design of CH/π interaction sites in a basic resolving agent

A novel synthetic basic resolving agent, cis-1-aminobenz[f]indan-2-ol (ABI), was rationally designed by introducing effective CH/π interaction sites to cis-1-aminoindan-2-ol (AI), whose chiral recognition ability has been reported from our laboratory. ABI was applicable to a wide variety of racemic arylalkanoic acids and showed moderate to excellent chiral recognition ability, which was obviously higher than that of AI. The fundamental and important role of CH/π interactions, such as tunable CH(sp2)/π and CH(sp 3)/π interactions, in the chiral recognition by ABI was revealed by X-ray crystallographic study.