111721-75-6 | 2-Bromo-3-fluoroaniline

CAS:111721-75-6 | 2-Bromo-3-fluoroaniline,Description

Synthesis Analysis

The synthesis of 2-Bromo-3-fluoroaniline and related compounds involves multiple steps, including nitration, chlorination, N-alkylation, reduction, and condensation. The synthesis process is often tailored to introduce specific functional groups that enable further chemical transformations. For instance, the synthesis of 1-(4-bromo-2-fluorophenyl)-1,3-dihydro-2H-imidazo[4,5-c]pyridin-2-one from pyridin-4-ol and 4-bromo-2-fluoroaniline through a series of reactions highlights the compound's utility in synthesizing complex molecules with biological activity (Wang et al., 2016).

Molecular Structure Analysis

The molecular structure of 2-Bromo-3-fluoroaniline derivatives is often determined using techniques like X-ray crystallography, NMR spectroscopy, and mass spectrometry. These methods provide insights into the compound's geometry, electronic configuration, and the spatial arrangement of atoms, which are crucial for understanding its reactivity and interaction with other molecules. For example, the crystal and molecular structure analysis of related halogenated anilines provides a foundation for predicting the behavior of 2-Bromo-3-fluoroaniline in various chemical contexts (Betz, 2015).

Chemical Reactions and Properties

2-Bromo-3-fluoroaniline participates in various chemical reactions, including palladium-catalyzed amination, halogen exchange, and coupling reactions, which are instrumental in synthesizing complex organic molecules. Its chemical properties, such as electrophilicity and reactivity towards nucleophiles, are significantly influenced by the presence of the bromo and fluoro groups, making it a versatile intermediate in organic synthesis. The compound's ability to undergo chemoselective functionalization is a key feature that is exploited in synthetic chemistry to achieve desired molecular transformations (Stroup et al., 2007).

Scientific Research Applications

• Synthesis and Biological Activities of New Derivatives : 2-Bromo-4-fluoroaniline was used as a starting material in the synthesis of thieno[3,2‐c]quinoline and pyrrolo[3,2‐c]quinoline derivatives. These compounds demonstrated significant antibacterial activity against both gram-positive and gram-negative bacteria, and one compound showed remarkable antifungal activity (Abdel‐Wadood et al., 2014) .
• Synthesis of Biologically Active Compounds : A compound derived from 4-bromo-2-fluoroaniline was synthesized as an important intermediate for various biologically active compounds, following a multi-step process involving nitration, chlorination, N-alkylation, reduction, and condensation (Wang et al., 2016).
• Application in Benzyne Cyclization : N-(2-bromoallyl)-N-methyl-2-fluoroaniline was used in an intramolecular addition to a tethered benzyne intermediate, leading to the formation of 4-functionalized 3-methylindoles (Barluenga et al., 1999).
• Synthesis of 2-Fluoro-4-bromobiphenyl : This compound, key for the manufacture of flurbiprofen, a non-steroidal anti-inflammatory and analgesic material, was synthesized from 2-fluoro-4-bromoaniline (Qiu et al., 2009).
• Syntheses of Sulfonated Derivatives : 2-Fluoroaniline, closely related to 2-Bromo-3-fluoroaniline, was used in synthesizing various sulfonated derivatives, which were then converted into other compounds, showcasing the versatility of fluoroanilines in chemical synthesis (Courtin, 1983) .

Safety And Hazards

2-Bromo-3-fluoroaniline is harmful if swallowed, in contact with skin, or if inhaled. It causes skin irritation and serious eye irritation. It may also cause respiratory irritation.

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