3-Bromo-2-chloro-9-phenyl-9H-carbazole
OLED intermediate, intermediates, 2576550-04-2
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3-Bromo-2-chloro-9-phenyl-9H-carbazole is a highly functionalized heterocyclic compound widely utilized in advanced organic synthesis and materials science. With the molecular formula C18H11BrClN, this molecule features a rigid carbazole core substituted with bromine and chlorine atoms at specific positions, alongside a phenyl group attached to the nitrogen atom. The precise structural arrangement significantly enhances its reactivity, making it an invaluable intermediate for constructing complex pharmaceutical agents and optoelectronic materials. While no single universally assigned CAS number exists without specific supplier verification due to potential variations in purity or salt forms, standard references often cite identifiers related to substituted carbazoles for similar derivatives; users are advised to verify exact catalog numbers with manufacturers like Sigma-Aldrich or specialized chemical suppliers.
The primary application of this compound lies in the development of organic light-emitting diodes (OLEDs) and organic photovoltaic cells. Its unique electronic properties, derived from the conjugated pi-system and halogen substituents, facilitate efficient charge transport and tunable bandgaps. Researchers frequently employ 3-bromo-2-chloro-9-phenyl-9H-carbazole as a key building block in cross-coupling reactions, such as Suzuki-Miyaura or Buchwald-Hartwig couplings, to synthesize high-performance luminescent polymers and small-molecule emitters. Furthermore, the presence of multiple halogen atoms allows for further diversification through nucleophilic substitution, enabling the creation of tailored ligands for catalysis or bioactive molecules with enhanced metabolic stability.
In the pharmaceutical sector, carbazole derivatives are investigated for their potential anticancer, antiviral, and anti-inflammatory activities. The specific substitution pattern of this molecule may offer improved binding affinity to biological targets compared to unsubstituted analogues. However, handling requires strict safety protocols, as halogenated aromatic compounds can be irritants or toxic upon exposure. Proper personal protective equipment and ventilation are essential during laboratory manipulation. Overall, 3-bromo-2-chloro-9-phenyl-9H-carbazole represents a versatile scaffold bridging fundamental organic chemistry with cutting-edge technological applications, driving innovation in next-generation display technologies and therapeutic drug discovery. Its availability supports rapid prototyping in R&D environments focused on functional materials.