18288-28-3

Basic information

• Product Name: 2-(2,5-dimethylphenyl)propanoic acid
• Synonyms: 2-(2,5-dimethylphenyl)propanoic acid
• CAS NO: 18288-28-3
• Molecular Weight: 178.231
• Mol File: 18288-28-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2-(2,5-dimethylphenyl)propanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2,5-dimethylphenyl)propanoic acid(18288-28-3)
• EPA Substance Registry System: 2-(2,5-dimethylphenyl)propanoic acid(18288-28-3)

Safety Data

• Hazardous Substances Data: 18288-28-3(Hazardous Substances Data)

Usage

Classification

Nonsteroidal anti-inflammatory drug (NSAID).

Common uses

Relieve pain, reduce fever, and decrease inflammation.

Mechanism of action

Inhibits the production of prostaglandins responsible for pain and inflammation.

Conditions treated

Arthritis, menstrual cramps, headaches, and muscle aches.

Availability

Over-the-counter in various forms, including tablets, capsules, and liquid suspension.

Tolerance

Generally well-tolerated when used as directed.

Risks with long-term or excessive use

Increased risk of side effects such as stomach ulcers, kidney damage, and heart problems.

Upstream product

• 83026-45-3 diethyl (2,5-dimethylphenyl)methylpropanedioate 
• 115144-84-8 2-(2,5-dimethyl-phenyl)-acrylic acid 
• 124-38-9 carbon dioxide 
• 2039-89-6 2,5-dimethylstyrene 
• 5779-94-2 2,5-dimethylbenzaldehyde 
• 13612-34-5 2-(2,5-dimethylphenyl)acetic acid 
• 74-88-4 methyl iodide 
• 106-42-3 para-xylene 
• 83026-29-3 diethyl acetoxy(2,5-dimethylphenyl)propanedioate 
• 83026-12-4 (2,5-dimethyl-phenyl)-hydroxy-malonic acid diethyl ester 
• 128228-14-8 3-<1-(2,5-dimethylphenyl)ethyl>-5,6-dihydro-1,4,2-dioxazine 

Downstream Products

• 134380-99-7 (R)-2-(2,5-dimethylphenyl)propanoic acid 
• 1239016-24-0 di(1-naphthyl)methyl (S)-2-(2,5-dimethylphenyl)propanoate 

Relevant articles and documents

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.

Iron-catalyzed, highly regioselective synthesis of α-aryl carboxylic acids from styrene derivatives and CO2

The iron-catalyzed hydrocarboxylation of aryl alkenes has been developed using a highly active bench-stable iron(II) precatalyst to give α-aryl carboxylic acids in excellent yields and with near-perfect regioselectivity. Using just 1 mol % FeCl2, bis(imino)pyridine 6 (1 mol %), CO 2 (atmospheric pressure), and a hydride source (EtMgBr, 1.2 equiv), a range of sterically and electronically differentiated aryl alkenes were transformed to the corresponding α-aryl carboxylic acids (up to 96% isolated yield). The catalyst was found to be equally active with a loading of 0.1 mol %. Preliminary mechanistic investigations show that an iron-catalyzed hydrometalation is followed by transmetalation and reaction with the electrophile (CO2).

Ester Enolates from α-Acetoxy Esters. Synthesis of Aryl Malonic and α-Aryl Alkanoic Esters from Aryl Nucleophiles and α-Keto Esters

Ester enolates are generated by reductive α-deacetoxylation of α-acetoxy-α-arylmalonic esters or α-acetoxy-α-arylalkanoic esters with lithium in liquid ammonia or sodium α-(dimethylamino)naphthalenide in hexamethylphosphoramide-benzene.Since the requisite α-acetoxy esters are available from aryl nucleophiles, the reductions provide effective new synthetic routes to arylmalonic esters and α-arylalkanoic esters.For example, 2-(p-isobutylphenyl)propionic acid (ibuprofen, a commercially important nonsteroidal antiinflammatory agent) is obtained in 73percent yield overall from isobutylbenzene.Arenes, aryllithiums, or arylmagnesium halides react with α-keto esters, e.g., diethyl oxomalonate, ethyl pyruvate, methyl phenylglyoxalate, or alkyl glyoxylates, to afford α-hydroxy esters.These are acetylated with acetic anhydride-triethylamine and p-(dimethylamino)pyridine as a catalyst.Reductive α-deoxygenation then allows replacement of the acetoxy group by hydrogen or an alkyl group.