215949-57-8

Basic information

• Product Name: 4-bromo-3-methylphenylacetic acid
• Synonyms: 4-bromo-3-methylphenylacetic acid;4-Bromo-3-methylbenzeneacetic acid;2-(4-Bromo-3-methylphenyl)
• CAS NO: 215949-57-8
• Molecular Formula: C9H9BrO2
• Molecular Weight: 229.07056
• Mol File: 215949-57-8.mol
• Article Data: 3

Chemical Properties

• Melting Point: 81℃
• Boiling Point: 338℃
• Flash Point: 158℃
• Appearance: /
• Density: 1.533
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.17±0.10(Predicted)
• CAS DataBase Reference: 4-bromo-3-methylphenylacetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-bromo-3-methylphenylacetic acid(215949-57-8)
• EPA Substance Registry System: 4-bromo-3-methylphenylacetic acid(215949-57-8)

Safety Data

• Hazardous Substances Data: 215949-57-8(Hazardous Substances Data)

Usage

General Description

4-bromo-3-methylphenylacetic acid, also known as 4-bromo-m-toluic acid, is an organic compound with a molecular formula of C9H9BrO2. This chemical falls under the category of bromobenzenes and is commonly utilized in laboratory settings. It typically exists as a white crystalline powder and operates as a reagent in many chemical reactions. The key functional groups in this compound include a bromine atom, a methyl group, and a carboxylic acid group, which significantly influence its chemical behavior. The presence of the bromine atom makes this compound relatively heavy, and assists in the identification of the presence of this compound due to bromine's characteristic in specific types of spectroscopic analysis.

Upstream product

• 1243245-66-0 tert-butyl 2-(4-bromo-3-methylphenyl)acetate 
• 621-36-3 m-methylphenylacetic acid 
• 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 articles and documents

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

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.