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• 2. Excitation energies from ground-state density-functionals by means of generator coordinates
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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Isoquinolines and derivatives Isoquinolines and derivatives
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Isoquinolines and derivatives

3-Bromo-6-Chloro-Isoquinoline: A Comprehensive Overview

The compound 3-bromo-6-chloro-isoquinoline, with CAS No. 1276056-79-1, is a heterocyclic aromatic compound belonging to the isoquinoline family. This molecule has garnered significant attention in the fields of organic chemistry, pharmacology, and materials science due to its unique structural properties and potential applications. The isoquinoline core, characterized by a fused benzene and pyridine ring system, serves as a versatile scaffold for various functional groups. In this case, the substitution of bromine at position 3 and chlorine at position 6 introduces distinct electronic and steric effects, making 3-bromo-6-chloro-isoquinoline a valuable compound for both academic research and industrial applications.

The synthesis of 3-bromo-6-chloro-isoquinoline typically involves multi-step organic reactions, often starting from readily available isoquinoline derivatives. One common approach is the nucleophilic substitution or electrophilic aromatic substitution to introduce the bromine and chlorine atoms at the desired positions. Recent advancements in catalytic methods and transition metal-mediated coupling reactions have significantly improved the efficiency and selectivity of these syntheses. For instance, the use of palladium catalysts in cross-coupling reactions has enabled the precise installation of halogen substituents on the isoquinoline ring system.

From a chemical standpoint, 3-bromo-6-chloro-isoquinoline exhibits interesting properties that make it a valuable compound for further exploration. The presence of electron-withdrawing groups like bromine and chlorine at positions 3 and 6 enhances the electrophilicity of the isoquinoline ring, making it more susceptible to nucleophilic attacks. This characteristic is particularly useful in designing molecules with specific reactivity profiles for applications in drug discovery and catalysis. Additionally, the steric hindrance introduced by these substituents can influence the molecule's conformational flexibility, which is critical in determining its interactions with biological targets.

In terms of applications, 3-bromo-6-chloro-isoquinoline has shown promise in several areas. In medicinal chemistry, it serves as a valuable intermediate for constructing bioactive molecules with potential therapeutic benefits. Recent studies have highlighted its role as a precursor in the synthesis of kinase inhibitors and other enzyme-targeting agents. Furthermore, its ability to act as a ligand in metalloorganic frameworks (MOFs) has opened new avenues in materials science for developing porous materials with tailored properties.

Recent research has also focused on understanding the photophysical properties of 3-bromo-6-chloro-isoquinoline. By incorporating this compound into light-emitting materials or sensors, scientists have demonstrated its potential in optoelectronic devices. For example, studies have shown that films incorporating this compound exhibit enhanced fluorescence quantum yields under specific conditions, making them suitable for applications in bioimaging or environmental sensing.

Moreover, computational studies have provided deeper insights into the electronic structure of 3-bromo-6-chloro-isoquinoline. Density functional theory (DFT) calculations have revealed that the substituents at positions 3 and 6 significantly alter the molecule's frontier molecular orbitals, influencing its reactivity towards various chemical transformations. These findings have been instrumental in guiding experimental efforts to optimize synthetic routes and tailor molecular properties for specific applications.

In conclusion, 3-bromo-6-chloro-isoquinoline stands as a testament to the versatility of isoquinoline derivatives in modern chemistry. Its unique combination of structural features and functional group reactivity positions it as a valuable tool for advancing both fundamental research and practical applications across diverse scientific disciplines.

• 286949-66-4(1H-Indole,2-bromo-5,6-dichloro-)
• 891842-50-5(2-Bromo-6-chloroquinoline)
• 1196156-59-8(2,6-Dibromo-4-chloropyridine)
• 22918-01-0(2-Bromo-4-chloropyridine)
• 1196155-73-3(1-Bromo-7-chloroisoquinoline)
• 925890-48-8(1-Bromo-4-chloroisoquinoline)
• 64658-05-5(2-Bromo-4-chloroquinoline)
• 40473-01-6(2-Bromo-5-chloropyridine)
• 120258-63-1(2-Bromo-3-chloroquinoline)
• 891842-52-7(2-Bromo-8-chloroquinoline)