601472-22-4

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
(S)-2-m-Tolyl-propionic acid is used as an intermediate in the synthesis of various pharmaceuticals and agrochemicals due to its unique chiral structure and reactivity. Its ability to be incorporated into complex molecules makes it a valuable component in the development of new drugs and agricultural products.
Used in Flavor and Fragrance Industry:
(S)-2-m-Tolyl-propionic acid is utilized as a key component in the production of flavor and fragrance ingredients. Its distinct odor and compatibility with organic solvents make it suitable for creating a wide range of scents and tastes for the food, beverage, and cosmetic industries.
Used as a Chiral Building Block in Organic Synthesis:
(S)-2-m-Tolyl-propionic acid is employed as a chiral building block in organic synthesis, particularly in the production of pharmaceuticals and other fine chemicals. Its chiral nature allows for the creation of enantiomerically pure compounds, which are essential in the development of more effective and selective medications.
Safety and Storage:
(S)-2-m-Tolyl-propionic acid is considered to be relatively stable under normal conditions. However, due to its potential for respiratory and skin irritation, it should be stored in a cool, dry place and handled in a well-ventilated area to ensure the safety of those working with the compound.

Upstream product

• 621-36-3 m-methylphenylacetic acid 
• 74-88-4 methyl iodide 
• 100-80-1 3-methylstyrene 
• 124-38-9 carbon dioxide 
• 620-23-5 m-tolyl aldehyde 
• 73721-06-9 2-(3-methylphenyl)propanoic acid 
• 1128278-76-1 2-(3-methylphenyl)acrylic acid 
• 201230-82-2 carbon monoxide 
• 2947-60-6 3-methylbenzyl cyanide 
• 620-14-4 1-Methyl-3-ethylbenzene 
• 16799-08-9 1-(2-bromoethyl)-3-methylbenzene 
• 53088-69-0 methyl 3-methylphenylacetate 
• 64-18-6 formic acid 
• 73720-82-8 2-mesyloxy-5-methyl-hydratropic acid 

Downstream Products

• 138457-19-9 (1R)-1-(3-methylphenyl)ethan-1-amine 
• 1265905-01-8 N-methoxy-N-methyl-2-(3-methylphenyl)propanamide 
• 1362735-84-9 C₁₈H₂₄N₂O₅ 
• 58358-37-5 2,5-dimethylphenylacetic acid ethyl ester 

Relevant academic research and scientific papers

PROCESS FOR THE PREPARATION OF A CHIRAL PROSTAGLANDIN ENOL INTERMEDIATE AND INTERMEDIATE COMPOUNDS USEFUL IN THE PROCESS

The present invention relates to a process for the preparation of a chiral prostaglandin enol intermediate of formula 1, comprising the steps of: separating a compound of formula 16-(R,S)-10 into its diastereomers by fractional crystallisation, reducing t

Catalytic α-Deracemization of Ketones Enabled by Photoredox Deprotonation and Enantioselective Protonation

This study reports the catalytic deracemization of ketones bearing stereocenters in the α-position in a single reaction via deprotonation, followed by enantioselective protonation. The principle of microscopic reversibility, which has previously rendered this strategy elusive, is overcome by a photoredox deprotonation through single electron transfer and subsequent hydrogen atom transfer (HAT). Specifically, the irradiation of racemic pyridylketones in the presence of a single photocatalyst and a tertiary amine provides nonracemic carbonyl compounds with up to 97% enantiomeric excess. The photocatalyst harvests the visible light, induces the redox process, and is responsible for the asymmetric induction, while the amine serves as a single electron donor, HAT reagent, and proton source. This conceptually simple light-driven strategy of coupling a photoredox deprotonation with a stereocontrolled protonation, in conjunction with an enrichment process, serves as a blueprint for other deracemizations of ubiquitous carbonyl compounds.

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.

Deracemizing α-Branched Carboxylic Acids by Catalytic Asymmetric Protonation of Bis-Silyl Ketene Acetals with Water or Methanol

We report a highly enantioselective catalytic protonation of bis-silyl ketene acetals. Our method delivers α-branched carboxylic acids, including nonsteroidal anti-inflammatory arylpropionic acids such as Ibuprofen, in high enantiomeric purity and high yields. The process can be incorporated in an overall deracemization of α-branched carboxylic acids, involving a double deprotonation and silylation followed by the catalytic asymmetric protonation.

Site-Selective, Remote sp3 C?H Carboxylation Enabled by the Merger of Photoredox and Nickel Catalysis

A photoinduced carboxylation of alkyl halides with CO2 at remote sp3 C?H sites enabled by the merger of photoredox and Ni catalysis is described. This protocol features a predictable reactivity and site selectivity that can be modulated by the ligand backbone. Preliminary studies reinforce a rationale based on a dynamic displacement of the catalyst throughout the alkyl side chain.

Photocarboxylation of Benzylic C-H Bonds

The carboxylation of sp3-hybridized C-H bonds with CO2 is a challenging transformation. Herein, we report a visible-light-mediated carboxylation of benzylic C-H bonds with CO2 into 2-arylpropionic acids under metal-free conditions. Photo-oxidized triisopropylsilanethiol was used as the hydrogen atom transfer catalyst to afford a benzylic radical that accepts an electron from the reduced form of 2,3,4,6-tetra(9H-carbazol-9-yl)-5-(1-phenylethyl)benzonitrile generated in situ. The resulting benzylic carbanion reacts with CO2 to generate the corresponding carboxylic acid after protonation. The reaction proceeded without the addition of any sacrificial electron donor, electron acceptor or stoichiometric additives. Moderate to good yields of the desired products were obtained in a broad substrate scope. Several drugs were successfully synthesized using the novel strategy.

Regioselectivity inversion tuned by iron(iii) salts in palladium-catalyzed carbonylations

Impactful regioselectivity control is crucial for cost-effective chemical synthesis. By using cheap and abundant iron(iii) salts, the hydroxycarbonylations of both aromatic and aliphatic alkenes were significantly enhanced in both reactivity and selectivity (iso/n or n/iso up to >99:1). Moreover, Pd-catalyzed carbonylation selectivity can be switched from branched to linear by using different Fe(iii) salts. In addition, similar results were obtained for the carbonylation of secondary alcohols.

A Ligand-Directed Catalytic Regioselective Hydrocarboxylation of Aryl Olefins with Pd and Formic Acid

An effective Pd-catalyzed hydrocarboxylation of aryl olefins with Ac2O and formic acid is described. A variety of 2- and 3-arylpropanoic acids can be regioselectively formed by the judicious choice of ligand without the use of toxic CO gas.

Synthesis of Bicyclo[n.1.0]alkanes by a Cobalt-Catalyzed Multiple C(sp3)?H Activation Strategy

A cobalt-catalyzed dual C(sp3)?H activation strategy has been developed and it provides a novel strategy for the synthesis of bicyclo[4.1.0]heptanes and bicyclo[3.1.0]hexanes. A key to the success of this reaction is the conformation-induced methylene C(sp3)?H activation of the resulting cobaltabicyclo[4.n.1] intermediate. In addition, the synthesis of bicyclo[3.1.0]hexane from pivalamide, by a triple C(sp3)?H activation, has also been demonstrated.

Cp2TiCl2-Catalyzed Regioselective Hydrocarboxylation of Alkenes with CO2

Cp2TiCl2-catalyzed regioselective hydrocarboxylation of alkenes with CO2 to give carboxylic acids in high yields has been developed in the presence of iPrMgCl. The reaction proceeds with a wide range of alkenes under mild conditions. Styrene and its derivatives can transform to α-aryl carboxylic acids, and aliphatic alkenes can transform to form alkanoic acids.