105879-63-8

Basic information

• Product Name: (2S)-2-(4-Chlorophenyl)propanoic acid
• Synonyms: (2S)-2-(4-Chlorophenyl)propanoic acid
• CAS NO: 105879-63-8
• Molecular Formula: C₉H₉ClO₂
• Molecular Weight: 184.61956
• Mol File: 105879-63-8.mol
• Article Data: 21

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2S)-2-(4-Chlorophenyl)propanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-2-(4-Chlorophenyl)propanoic acid(105879-63-8)
• EPA Substance Registry System: (2S)-2-(4-Chlorophenyl)propanoic acid(105879-63-8)

Safety Data

• Hazardous Substances Data: 105879-63-8(Hazardous Substances Data)

Usage

Description

(2S)-2-(4-Chlorophenyl)propanoic acid, commonly known as ibuprofen, is a nonsteroidal anti-inflammatory drug (NSAID) with the molecular formula C9H9ClO2. It is a chiral compound, with the (2S) configuration indicating the arrangement of atoms in its structure. Ibuprofen is widely recognized for its analgesic, antipyretic, and anti-inflammatory properties.

Uses

Used in Pharmaceutical Industry:
(2S)-2-(4-Chlorophenyl)propanoic acid is used as an analgesic for the relief of mild to moderate pain, such as headaches, menstrual cramps, and musculoskeletal discomfort. It is effective due to its ability to inhibit the synthesis of prostaglandins, which are involved in the sensation of pain and inflammation.
Used in Anti-inflammatory Applications:
In the medical field, (2S)-2-(4-Chlorophenyl)propanoic acid serves as an anti-inflammatory agent, reducing inflammation associated with conditions like arthritis. Its mechanism of action involves the inhibition of cyclooxygenase (COX) enzymes, which are responsible for the production of prostaglandins that mediate inflammation.
Used in Antipyretic Therapy:
(2S)-2-(4-Chlorophenyl)propanoic acid is utilized as an antipyretic to reduce fever. It achieves this by acting on the hypothalamus to reset the body's temperature regulation, thereby lowering elevated body temperatures.
Used in Over-the-Counter Medications:
As a widely available over-the-counter medication, (2S)-2-(4-Chlorophenyl)propanoic acid is used for self-treatment of various conditions, including minor aches, pains, and fevers. Its accessibility and recognized safety profile when used as directed make it a popular choice for consumers seeking relief from common ailments.

Upstream product

• 130405-71-9 (±)-ethyl 2-(4-chlorophenyl)propanoate 
• 2184-88-5 2-(4-chlorophenyl)propionitrile 
• 938-95-4 2-(4-Chloro-phenyl)-propionic acid 
• 62784-66-1 bis(1-naphthyl)methanol 
• 1059200-71-3 (2'S,4R)-3-[2-(4-chlorophenyl)propionyl]-4-phenyloxazolidin-2-one 
• 1073-67-2 4-vinylbenzyl chloride 
• 201230-82-2 carbon monoxide 
• 51747-43-4 2-(4-chlorophenyl)-acrylic acid 
• 108-90-7 chlorobenzene 
• 286964-62-3 2-(4-chlorophenyl)propanal 
• 1712-70-5 1-chloro-4-(1-methylethenyl)-benzene 
• 465529-75-3 tert-butyl 2-(4-chlorophenyl)propanoate 
• 873-73-4 4-n-chlorophenylacetylene 
• 64-18-6 formic acid 

Downstream Products

• 137044-27-0 methyl (S)-2-(4-chlorophenyl)propanoate 
• 762300-23-2 (2S)-2-(4-chlorophenyl)-N-(3-{4-[5-(isobutyrylamino)-2-methylphenyl]-1-piperidinyl}propyl)propanamide 
• 951016-04-9 (R)-methyl 2-(5-((S)-2-(4-chlorophenyl)propanamido)-1-oxoisoquinolin-2(1H)-yl)-3-methylbutanoate 
• 1208553-06-3 C₁₂H₁₁ClN₂OS 
• 1095321-17-7 (S)-2-(3-fluorophenyl)propanoic acid 
• 10516-54-8 (R)-2-(4'-biphenylyl)propanoic acid 

Relevant articles and documents

Chemoenzymatic synthesis of pure enantiomeric 2-aryl propionic acids

A new chemoenzymatic procedure to obtain pure enantiomeric 2-arylpropionic acids is described. The one pot synthesis of (±)-2-arylpropionic acids is carried out by addition of dichlorocarbene to the C=O bond of arylmethylketones and hydrogenolysis of the additon product. The racemic mixture is resolved by enantiospecific hydrolysis of the racemic ethyl esters using native lipase from Candida rugosa. The good yields, the accessibility of the starting arylmethylketones and the stereospecificity of the enzymatic hydrolysis make the process interesting in order to obtain the same non steroidal antiinflammatory drugs such as Ibuprofen or Naproxen.

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.