201849-14-1 | 2-BROMO-6-CHLORO-4-FLUOROANILINE

CAS:201849-14-1 | 2-BROMO-6-CHLORO-4-FLUOROANILINE,Description

2-Bromo-6-chloro-4-fluoroaniline is a halogenated aniline, a class of compounds known for their reactivity and utility in organic synthesis. The presence of bromo, chloro, and fluoro substituents on the benzene ring makes it a compound of interest for various chemical transformations and applications in materials science, pharmaceuticals, and agrochemicals.

Synthesis Analysis

The synthesis of halogenated anilines typically involves the direct halogenation of aniline compounds or through diazonium salt reactions. While specific synthesis routes for 2-Bromo-6-chloro-4-fluoroaniline are not directly reported, methodologies for similar compounds suggest the potential for halogen dance reactions, diazotization, and subsequent halogen substitution to achieve the desired halogenation pattern (Wu et al., 2022; Jiang-he, 2010).

Molecular Structure Analysis

The molecular structure of halogenated anilines is characterized by the presence of halogen atoms on the benzene ring, which significantly influences the electronic distribution and molecular geometry. Crystal and molecular structure analyses of similar compounds indicate monoclinic crystal systems with significant intra- and intermolecular interactions, including hydrogen bonds and halogen···halogen interactions, which could be expected in 2-Bromo-6-chloro-4-fluoroaniline as well (Betz, 2015).

Chemical Reactions and Properties

The reactivity of 2-Bromo-6-chloro-4-fluoroaniline can be anticipated from the electrophilic nature of its halogen substituents, making it a valuable intermediate for nucleophilic substitution reactions (SNAr), coupling reactions, and in the synthesis of complex organic molecules. Studies on related compounds demonstrate a variety of chemical transformations, including amination, halogen exchange, and coupling reactions, which underscore the compound's versatility in synthetic chemistry (Stroup et al., 2007).

Physical Properties Analysis

The physical properties of halogenated anilines like 2-Bromo-6-chloro-4-fluoroaniline are influenced by their molecular structure and halogen content. These compounds typically exhibit solid state at room temperature, with specific melting points, boiling points, and solubility characteristics that depend on the nature and position of the halogen substituents. The monoclinic crystal structure and detailed vibrational spectroscopy studies provide insights into the compound's stability and intermolecular interactions (Betz, 2015).

Chemical Properties Analysis

The chemical properties of 2-Bromo-6-chloro-4-fluoroaniline, including its acidity, basicity, and reactivity towards various reagents, are defined by the aniline moiety and the electron-withdrawing effects of the halogen atoms. These properties influence its behavior in chemical reactions, such as its nucleophilicity and electrophilicity, and its interaction with acids and bases. The presence of halogens also imparts unique reactivity patterns, facilitating selective substitution reactions that are valuable in synthetic applications (Stroup et al., 2007).

Scientific Research Applications

Crystal and Molecular Structure Analysis

Research on compounds structurally similar to 2-Bromo-6-chloro-4-fluoroaniline, like 2,6-dibromo-3-chloro-4-fluoroaniline, has focused on understanding their crystal and molecular structures. These studies involve determining the crystal properties such as monoclinic structure, specific dimensions, and observing classical intra- and intermolecular hydrogen bonds and halogen interactions within the crystal structure (Betz, 2015).

Metabolic Pathways in Biological Systems

The metabolism of halogenated anilines, including those structurally similar to 2-Bromo-6-chloro-4-fluoroaniline, has been studied in rat liver microsomal systems. These studies identify various metabolites from side-chain C-hydroxylation and N-hydroxylation, providing insight into how these compounds are metabolized in biological systems (Boeren et al., 1992).

Dielectric Properties

The dielectric properties of halogen-substituted anilines have been investigated, which may have implications for the study of 2-Bromo-6-chloro-4-fluoroaniline. These studies focus on understanding the dielectric absorption and relaxation times of these molecules in various conditions, providing valuable information for materials science and molecular physics (Vyas & Vashisth, 1988).

Synthesis and Chemical Reactions

Research on the synthesis of compounds related to 2-Bromo-6-chloro-4-fluoroaniline, such as 4-Bromo-2-fluorobiphenyl, reveals methods and conditions for efficient synthesis and potential applications in chemical manufacturing (Yong-qiang, 2012).

Safety And Hazards

2-Bromo-6-chloro-4-fluoroaniline is harmful if swallowed, in contact with skin, or if inhaled. It may cause respiratory irritation and serious eye irritation. It also causes skin irritation.

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