627871-16-3 | 5-BROMO-4-FLUORO-2-METHYLANILINE

CAS:627871-16-3 | 5-BROMO-4-FLUORO-2-METHYLANILINE,Description

Synthesis Analysis

The synthesis of halogenated aromatic compounds often involves regioselective halogenation, nucleophilic substitution, and the use of protecting groups. For instance, the synthesis of 5-bromo-2-methoxy-6-methylaminopyridine-3-carboxylic acid involved a series of reactions including methoxylation, oxidation, and bromination to achieve the desired product with a high degree of regioselectivity. Similarly, the synthesis of 5-(4-bromophenylamino)-2-methylsulfanylmethyl-2H-1,2,3-triazol-4-carboxylic acid ethyl ester was achieved through a sequence of reactions starting from p-bromoaniline, highlighting the versatility of bromo-substituted anilines as intermediates.

Molecular Structure Analysis

The molecular structure of halogenated aromatic compounds is often characterized using spectroscopic methods such as NMR, IR, and X-ray crystallography. For example, the Schiff base compound 4-bromo-2-[(E)-6-methyl-2-pyridyliminomethyl]phenol was characterized by X-ray single-crystal diffraction, which provided detailed information about its molecular geometry. The structural analysis of these compounds can reveal the influence of substituents on the overall molecular conformation and stability.

Chemical Reactions Analysis

Halogenated aromatic compounds can participate in various chemical reactions, including nucleophilic aromatic substitution and coupling reactions. The presence of halogens can significantly affect the reactivity of the aromatic ring. For instance, the radiosynthesis of 2-amino-5-[18F]fluoropyridines was achieved by a palladium-catalyzed amination reaction of 2-bromo-5-[18F]fluoropyridine, demonstrating the utility of bromo-fluoropyridines in radiochemical syntheses.

Physical and Chemical Properties Analysis

The physical and chemical properties of halogenated aromatic compounds are influenced by the nature and position of the substituents on the aromatic ring. For example, the Schiff-base molecule 4-bromo-5-fluoro-2-((3-nitrophenylimino)methyl)phenol was investigated using DFT calculations, which provided insights into its vibrational frequencies, electronic properties, and molecular electrostatic potential. These properties are crucial for understanding the behavior of such compounds in different environments and their potential applications in medicinal chemistry.

Scientific Research Applications

Metabolism Studies

• Microsomal Metabolism of Halogenated 4-Methylanilines: Rat liver microsomal metabolism of halogenated 4-methylanilines, including 2-bromo-4-methylaniline, was investigated. This study identified metabolites resulting from side-chain C-hydroxylation and N-hydroxylation, providing insights into the metabolic pathways of similar compounds (Boeren et al., 1992).

Chemical Reactions

• Reactivity with Hemoglobin: Research on 4-bromo-N,N-dimethylaniline-N-Oxide, a compound related to 5-Bromo-4-fluoro-2-methylaniline, showed transformations with hemoglobin, leading to various products. This study contributes to understanding the chemical interactions of similar brominated compounds (Renner, 2004).

Environmental Toxicology

• Toxicity Assessment in Earthworms: A study on 2-fluoro-4-methylaniline in earthworms using NMR spectroscopy identified changes in endogenous metabolites. This research helps in understanding the environmental impact and toxicity of related compounds (Bundy et al., 2002) .

Synthesis and Properties

• Synthesis of Analogs via Suzuki Cross-Coupling: A study described the synthesis of 4-bromo-N-((3-bromothiophen-2-yl)methylene)-2-methylaniline analogs, offering insights into the synthesis process and properties of similar bromo-fluoro compounds (Rizwan et al., 2021).

Steric and Electronic Effects

• Influence on SNAr Reactions: Research on steric and electronic effects of halogenated compounds like 1-bromo-2-fluoro-3,5-dinitrobenzenes provides insights into the reaction mechanisms of similar bromo-fluoro derivatives (Onyido & Hirst, 1991).

Safety And Hazards

The compound is classified as Acute Tox. 3 Oral. It has hazard statements H302, H315, H319, H332, H335, indicating that it is harmful if swallowed, causes skin irritation, causes serious eye irritation, harmful if inhaled, and may cause respiratory irritation. Precautionary measures include avoiding breathing dust/fume/gas/mist/vapors/spray, wearing protective gloves/protective clothing/eye protection/face protection, and rinsing cautiously with water for several minutes in case of contact with eyes.

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