24470-14-2

Basic information

• Product Name: (S)-(+)-2-(4'-methoxyphenyl)propanoic acid
• Synonyms: (S)-(+)-2-(4'-methoxyphenyl)propanoic acid
• CAS NO: 24470-14-2
• Molecular Weight: 180.203
• Mol File: 24470-14-2.mol
• Article Data: 17

Chemical Properties

• CAS DataBase Reference: (S)-(+)-2-(4'-methoxyphenyl)propanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-2-(4'-methoxyphenyl)propanoic acid(24470-14-2)
• EPA Substance Registry System: (S)-(+)-2-(4'-methoxyphenyl)propanoic acid(24470-14-2)

Safety Data

• Hazardous Substances Data: 24470-14-2(Hazardous Substances Data)

Usage

Description

(S)-(+)-2-(4'-methoxyphenyl)propanoic acid, a chemical compound with the molecular formula C10H12O3, is a derivative of 4-methoxyphenylpropanoic acid and belongs to the class of propionic acids. (S)-(+)-2-(4'-methoxyphenyl)propanoic acid is characterized by its chiral nature and is often utilized in various chemical and pharmaceutical applications due to its unique properties.

Uses

Used in Asymmetric Synthesis:
(S)-(+)-2-(4'-methoxyphenyl)propanoic acid is used as a chiral auxiliary in asymmetric synthesis for enhancing the selectivity and yield of enantiomerically pure compounds. Its ability to induce chirality in the products makes it a valuable tool in the synthesis of complex organic molecules.
Used in Organic Synthesis:
As a building block in organic synthesis, (S)-(+)-2-(4'-methoxyphenyl)propanoic acid is employed for constructing a wide range of organic compounds, including pharmaceuticals and agrochemicals. Its versatile structure allows for various functional group transformations and incorporation into more complex molecules.
Used in Pharmaceutical Production:
(S)-(+)-2-(4'-methoxyphenyl)propanoic acid is used as a key component in the production of pharmaceuticals. Its potential antioxidant, anti-inflammatory, and analgesic properties make it a promising candidate for the development of new drugs targeting various medical conditions.
Used in Agrochemicals:
In the agrochemical industry, (S)-(+)-2-(4'-methoxyphenyl)propanoic acid is used as a starting material for the synthesis of various agrochemicals, such as pesticides and herbicides. Its unique properties contribute to the development of effective and targeted agricultural products.
Used in Antioxidant Applications:
(S)-(+)-2-(4'-methoxyphenyl)propanoic acid has been studied for its potential antioxidant properties, which could be beneficial in the development of products that protect cells from oxidative damage, a common factor in many diseases.
Used in Anti-inflammatory Applications:
(S)-(+)-2-(4'-methoxyphenyl)propanoic acid's potential anti-inflammatory properties make it a candidate for the development of new treatments for inflammatory conditions, such as arthritis and other autoimmune diseases.
Used in Analgesic Applications:
As a potential analgesic, (S)-(+)-2-(4'-methoxyphenyl)propanoic acid could be used in the development of new pain-relieving medications, offering alternative options for patients in need of effective pain management.

Upstream product

• 31007-06-4 2-(4-methoxyphenyl)propionitrile 
• 637-69-4 4-Methoxystyrene 
• 201230-82-2 carbon monoxide 
• 138623-00-4 tert-butyl α-(4-methoxyphenyl)propionate 
• 93397-63-8 (S)-4-methoxy-β-methylbenzeneethanol 
• 252058-33-6 2-(4-methoxyphenyl)propanal 
• 100-66-3 methoxybenzene 
• 117177-66-9 2-(4-methoxyphenyl)-2-oxoacetyl chloride 
• 1429641-12-2 C₁₀H₉ClO₂ 
• 51747-42-3 2-(4-methoxy-phenyl)-acrylic acid 
• 942-54-1 2-(4-methoxyphenyl)propanoic acid 
• 62784-66-1 bis(1-naphthyl)methanol 
• 23786-14-3 4-methoxy-phenyl acetic acid methyl ester 
• 50415-73-1 methyl 2-(4-methoxyphenyl)propionate 

Downstream Products

• 129411-29-6 4'-((R)-1-Methyl-heptyloxy)-biphenyl-4-carboxylic acid 4-((S)-1-butoxycarbonyl-ethyl)-phenyl ester 
• 129411-33-2 4'-((R)-1-Methyl-heptyloxy)-biphenyl-4-carboxylic acid 4-[(S)-1-(butyl-methyl-carbamoyl)-ethyl]-phenyl ester 
• 129411-32-1 4'-Octyloxy-biphenyl-4-carboxylic acid 4-[(S)-1-(butyl-methyl-carbamoyl)-ethyl]-phenyl ester 
• 129411-28-5 4'-Decyloxy-3'-fluoro-biphenyl-4-carboxylic acid 4-((S)-1-butoxycarbonyl-ethyl)-phenyl ester 
• 129411-31-0 4'-Octyloxy-biphenyl-4-carboxylic acid 4-[(S)-1-((R)-1-methyl-heptyloxycarbonyl)-ethyl]-phenyl ester 
• 129411-30-9 4'-Octyloxy-biphenyl-4-carboxylic acid 4-[(S)-1-((S)-1-methyl-heptyloxycarbonyl)-ethyl]-phenyl ester 
• 143589-99-5 (1S)-N-benzyloxycarbonyl-1-(4-methoxy-phenyl)ethylamine 
• 111197-94-5 methyl (S)-2-(4-methyoxyphenyl)propionate 
• 132786-62-0 (S)-2-(4-Hydroxy-phenyl)-propionic acid (S)-1-methyl-heptyl ester 
• 132786-63-1 (S)-2-(4-Hydroxy-phenyl)-propionic acid (R)-1-methyl-heptyl ester 
• 129411-26-3 (S)-N-Butyl-2-(4-hydroxy-phenyl)-N-methyl-propionamide 

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.

Biocatalytic Parallel Interconnected Dynamic Asymmetric Disproportionation of α-Substituted Aldehydes: Atom-Efficient Access to Enantiopure (S)-Profens and Profenols

The biocatalytic asymmetric disproportionation of aldehydes catalyzed by horse liver alcohol dehydrogenase (HLADH) was assessed in detail on a series of racemic 2-arylpropanals. Statistical optimization by means of design of experiments (DoE) allowed the identification of critical interdependencies between several reaction parameters and revealed a specific experimental window for reaching an ′optimal compromise′ in the reaction outcome. The biocatalytic system could be applied to a variety of 2-arylpropanals and granted access in a redox-neutral manner to enantioenriched (S)-profens and profenols following a parallel interconnected dynamic asymmetric transformation (PIDAT). The reaction can be performed in aqueous buffer at ambient conditions, does not rely on a sacrificial co-substrate, and requires only catalytic amounts of cofactor and a single enzyme. The high atom-efficiency was exemplified by the conversion of 75 mM of rac-2-phenylpropanal with 0.03 mol% of HLADH in the presence of ～0.013 eq. of oxidized nicotinamide adenine dinucleotide (NAD+), yielding 28.1 mM of (S)-2-phenylpropanol in 96% ee and 26.5 mM of (S)-2-phenylpropionic acid in 89% ee, in 73% overall conversion. Isolated yield of 62% was obtained on 100 mg-scale, with intact enantiopurities. (Figure presented.).

Ferrocenyl chiral bisphosphorus ligands for highly enantioselective asymmetric hydrogenation via noncovalent ion pair interaction

A new class of ferrocenyl chiral bisphosphorus ligand, Wudaphos, was developed, and exhibits excellent ee and activity (ee up to 99%, TON up to 20000) for the asymmetric hydrogenation of both 2-aryl and 2-alkyl acrylic acids through ion pair noncovalent interaction under base free and mild reaction conditions. Well-known anti-inflammatory drugs such as naproxen and ibuprofen together with the intermediate for the preparation of Roche ester and some bioactive compounds were also efficiently obtained with excellent ee. Control experiments were conducted and revealed that the ion pair noncovalent interaction and chain length played important roles.