215949-57-8

Usage

Uses

Used in Chemical Synthesis:
4-bromo-3-methylphenylacetic acid is used as a chemical intermediate for the synthesis of various organic compounds. Its unique functional groups, including the bromine atom, methyl group, and carboxylic acid, make it a versatile building block in the preparation of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Laboratory Research:
4-bromo-3-methylphenylacetic acid is used as a reagent in laboratory research for studying chemical reactions and mechanisms. Its distinct properties, such as the presence of the bromine atom, allow researchers to investigate the effects of halogenation on reaction pathways and the influence of substituents on reaction outcomes.
Used in Spectroscopic Analysis:
4-bromo-3-methylphenylacetic acid is used as a reference compound in spectroscopic analysis, particularly in techniques that involve the identification and characterization of organic compounds. The characteristic features of the bromine atom in the compound make it a valuable tool for understanding the behavior of similar compounds in various spectroscopic methods.
Used in Material Science:
4-bromo-3-methylphenylacetic acid is used as a precursor in the development of new materials, such as polymers and coatings, that exhibit specific properties. The presence of the bromine atom and other functional groups in the compound can influence the physical and chemical characteristics of the resulting materials, making them suitable for various applications in material science.

Upstream product

• 621-36-3 m-methylphenylacetic acid 
• 1243245-66-0 tert-butyl 2-(4-bromo-3-methylphenyl)acetate 
• 792917-14-7 (4-bromo-3-methyl-phenyl)-acetic acid amide 

Downstream Products

• 1372409-16-9 C₁₉H₂₂BrN 
• 1372409-11-4 C₁₉H₂₂BrN 
• 1372409-17-0 C₁₉H₂₂BrN 
• 1372409-12-5 C₁₉H₂₂BrN 

Relevant academic research and scientific papers

Regioisomerism in the synthesis of a chiral aminotetralin drug compound: Unraveling mechanistic details and diastereomer-specific in-depth NMR investigations

During chemical process development of a novel 2-aminotetralin derivative intended for use as an antidepressant, scrutiny of the byproduct present in the drug molecule revealed a set of regioisomers. Detailed studies showed that this impurity issue origin

N- (HETERO)ARYL, 2- (HETERO)ARYL-SUBSTITUTED ACETAMIDES FOR USE AS WNT SIGNALING MODULATORS

The present invention relates to compounds of formulae 1 and 2 and methods for modulating the Wnt signaling pathway using these compounds, wherein A1, A2, B, Y and Z all represent rings.

Optimization and scale-up of a Pd-catalyzed aromatic C-N bond formation: A key step in the synthesis of a novel 5-HT1B receptor antagonist

Searching for the best synthetic route for a given target molecule is a complex task and, by the same token, a key deliverable from a process R&D department. In this vein the challenge for our group was to identify a sustainable manufacturing process for a chiral compound, AR-A2, to be developed for the treatment of certain neurological disorders. Besides designing a method for assembling the core (R)-2-aminotetralin nucleus, a key feature in the overall synthesis was to provide a robust procedure for creating a new C-N bond between an aromatic ring and a heterocyclic moiety. The methodology employed a Buchwald-Hartwig coupling, and a highly efficient catalytic process was developed using Pd(OAc)2 as precatalyst, with loadings as low as 0.47 mol % (in laboratory trials one order of magnitude lower) together with (R)-BINAP as ligand. Optimizing the reaction conditions allowed a virtually quantitative conversion of the brominated aromatic substrate after heating to 110-115 °C in toluene for 4 h. Telescoping this step with a succeeding catalytic hydrogenation to effect an N-debenzylation, followed by precipitation of the benzoate salt offered an overall yield for the two consecutive steps of 88% at 125-kg batch size, combined with excellent stereochemical product purity of 98% ee.