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Comprehensive Overview of 1-Bromoisoquinolin-4-amine (CAS No. 55404-28-9): Properties, Applications, and Research Insights

1-Bromoisoquinolin-4-amine (CAS No. 55404-28-9) is a specialized heterocyclic compound that has garnered significant attention in pharmaceutical and materials science research. This brominated derivative of isoquinoline features a unique molecular structure, combining a bromo substituent with an amine functional group at the 4-position. Its chemical formula, C₉H₇BrN₂, and molecular weight of 223.07 g/mol make it a versatile intermediate in synthetic chemistry.

The compound's isoquinoline core is a privileged scaffold in drug discovery, often associated with bioactive molecules targeting neurological and metabolic disorders. Researchers have explored 1-Bromoisoquinolin-4-amine as a building block for kinase inhibitors and G-protein-coupled receptor (GPCR) modulators, aligning with current trends in precision medicine and targeted therapy development. Its bromine atom offers strategic reactivity for cross-coupling reactions, particularly in palladium-catalyzed transformations like Suzuki-Miyaura or Buchwald-Hartwig couplings.

In material science, 55404-28-9 has shown promise in the synthesis of organic semiconductors and luminescent materials. The compound's ability to participate in π-stacking interactions due to its aromatic system makes it valuable for designing optoelectronic devices, a rapidly growing field driven by demand for flexible displays and energy-efficient lighting solutions. Recent studies highlight its potential in creating small-molecule OLEDs (organic light-emitting diodes) with improved color purity.

Analytical characterization of 1-Bromoisoquinolin-4-amine typically involves HPLC purification, mass spectrometry, and NMR spectroscopy (particularly ¹H and ¹³C). The compound generally appears as a light yellow to beige crystalline powder with a melting point range of 145-150°C. Stability studies recommend storage under inert atmosphere at 2-8°C to prevent degradation, especially for long-term preservation.

From a synthetic chemistry perspective, this compound addresses several modern challenges in green chemistry. Researchers are investigating its use in atom-economical reactions and cascade transformations that minimize waste generation. The amine group at the 4-position provides an excellent handle for further derivatization through acylation, reductive amination, or click chemistry approaches, making it valuable for combinatorial library synthesis.

In the context of structure-activity relationship (SAR) studies, 1-Bromoisoquinolin-4-amine serves as a critical probe for understanding how bromine substitution patterns influence biological activity in isoquinoline-based compounds. This aligns with current pharmaceutical industry focus on halogen bonding interactions in drug design, where bromine's unique electronic properties can enhance target binding affinity and metabolic stability.

The compound's commercial availability through specialty chemical suppliers has expanded in recent years, reflecting growing demand from both academic and industrial researchers. Pricing trends show variability based on purity grades (typically 95-98%) and batch sizes, with current market dynamics influenced by raw material availability for bromination reactions. Proper handling requires standard laboratory precautions, including use of personal protective equipment and adequate ventilation.

Emerging applications include its use as a precursor for fluorescent probes in biological imaging and as a ligand in transition metal catalysis. The compound's photophysical properties are being explored for bioorthogonal chemistry applications, particularly in live-cell labeling strategies. These developments position 55404-28-9 at the intersection of multiple cutting-edge research domains.

Future research directions may explore the compound's potential in proteolysis targeting chimera (PROTAC) design or as a fragment in DNA-encoded library technology. The continued evolution of C-H activation methodologies may further enhance the synthetic utility of this brominated isoquinoline derivative, offering more sustainable routes to complex molecular architectures.

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