Product name: 6-Bromo-4-methoxy-1H-indazole
Cas No.: 885519-21-1
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6-Bromo-4-methoxy-1H-indazole (CAS: 885519-21-1) is a bromo-substituted indazole heterocycle widely used as an important intermediate in chemical and pharmaceutical research. Below is a detailed overview of its functions and applications:
1. Chemical Uses
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Pharmaceutical Intermediate
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This compound is commonly used in the optimization of new drug molecules, especially in the design of kinase inhibitors, anticancer drugs, anti-inflammatory agents, and CNS-active compounds.
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The indazole ring is a key scaffold in many drugs, such as:
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Indazole-based tyrosine kinase inhibitors (e.g., Vemurafenib, Tivantinib)
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PDE inhibitors (used in cardiovascular or antidepressant research)
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The 6-bromo substitution provides an active site for further functionalization, suitable for coupling reactions such as Suzuki, Sonogashira, and Buchwald–Hartwig to generate various derivatives.
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Organic Synthesis Reagent
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Serves as an intermediate for heterocyclic substitution reactions in the synthesis of complex molecules, materials chemistry, and polymer studies.
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The bromine atom’s reactivity allows it to act as a substrate in cross-coupling reactions, enabling the introduction of new aryl or alkyl groups.
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2. Role in Research and Drug Discovery
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Used in lead compound discovery to construct small-molecule libraries.
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Important for Structure–Activity Relationship (SAR) studies to analyze electronic and steric effects.
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Some reported derivatives show potential biological activities such as:
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Antitumor effects (by inhibiting BRAF, PI3K, etc.)
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Anti-inflammatory activity
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CNS modulation properties
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3. Applications in Materials and Optoelectronics (Secondary Use)
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Indazole derivatives have applications in OLED emitting materials and organic semiconductors, due to their conjugated structure and stability.
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The bromo-substituted structure facilitates coupling reactions to build extended π-conjugated systems.
Summary
| Category | Main Application |
|---|---|
| Pharmaceutical Chemistry | Intermediate for kinase inhibitors, anticancer and anti-inflammatory agents |
| Organic Synthesis | Substrate for coupling reactions, heterocyclic scaffold builder |
| Research Use | SAR studies, small-molecule library component |
| Materials Science | Potential monomer for OLEDs and organic electronics |
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