4-Bromo-7-chloro-6-fluoro-1H-indazole: Key Facts & FAQs
4-Bromo-7-chloro-6-fluoro-1H-indazole: Key Facts & FAQs
4-bromo-7-chloro-6-fluoro-1H-indazole is a trihalogenated bicyclic heterocyclic compound widely used as a versatile synthetic building block in medicinal chemistry and drug discovery research.
- Product SKU
- B175395
- Chemical Name
- 4-bromo-7-chloro-6-fluoro-1H-indazole
- Core Scaffold
- 1H-indazole (benzopyrazole) bicyclic heterocycle
- Halogen Substitution Pattern
- Bromo at C-4, chloro at C-7, fluoro at C-6
- Primary Application
- Synthetic intermediate and building block for medicinal chemistry and drug discovery
- Supplier
- Aladdin Scientific (aladdin-e.com)
Chemical Structure and Properties
4-Bromo-7-chloro-6-fluoro-1H-indazole belongs to the indazole family of bicyclic heterocycles, which consists of a benzene ring fused to a pyrazole ring. The compound carries three distinct halogen substituents: a bromine atom at the C-4 position, a chlorine atom at the C-7 position, and a fluorine atom at the C-6 position. This precise substitution pattern profoundly influences the compound's electronic distribution, lipophilicity, and reactivity profile.
The presence of fluorine at C-6 increases metabolic stability and can modulate the pKa of nearby functional groups — properties that are highly valued in drug design. The bromine at C-4 serves as a handle for transition-metal-catalyzed cross-coupling reactions (e.g., Suzuki, Buchwald-Hartwig, and Negishi couplings), while the chlorine at C-7 provides additional opportunities for selective functionalization under appropriate reaction conditions.
Applications in Medicinal Chemistry and Synthesis
Halogenated indazoles are recognized as privileged scaffolds in pharmaceutical research due to the indazole core's ability to mimic purine bases, form hydrogen bonds with biological targets, and penetrate cell membranes. 4-Bromo-7-chloro-6-fluoro-1H-indazole is primarily employed as a synthetic building block for the construction of more complex drug candidates and research tools.
The C-4 bromo substituent is particularly useful for palladium-catalyzed cross-coupling reactions, enabling researchers to introduce aryl, heteroaryl, alkyl, or amino groups with high selectivity. The C-7 chloro group can similarly participate in nucleophilic aromatic substitution or metal-catalyzed coupling under forcing conditions. Compounds derived from this scaffold may find application in kinase inhibitor programs, antiviral research, and central nervous system (CNS) drug discovery, areas where fluorinated heterocycles are especially prevalent.
Handling, Storage, and Safety
As with most organohalogen research compounds, 4-bromo-7-chloro-6-fluoro-1H-indazole should be handled with standard laboratory precautions. Researchers should wear appropriate personal protective equipment (PPE) including nitrile gloves, lab coat, and safety glasses. Work should be performed in a well-ventilated fume hood to minimize inhalation exposure to fine particles or vapors.
The compound should be stored in a cool, dry location away from light, moisture, and incompatible reagents such as strong oxidizers and bases. Sealed containers stored under inert atmosphere (nitrogen or argon) are recommended to preserve purity over extended periods. Always consult the Safety Data Sheet (SDS) provided by Aladdin Scientific before use. Disposal must comply with local regulations for halogenated organic waste.
Ordering and Specifications from Aladdin Scientific
4-Bromo-7-chloro-6-fluoro-1H-indazole is available from Aladdin Scientific under SKU B175395. Customers can place orders directly through the Aladdin Scientific website (aladdin-e.com) or contact the sales team for bulk inquiries, custom packaging, or expedited delivery options.
Aladdin Scientific provides a Certificate of Analysis (CoA) with each lot, detailing purity, appearance, and analytical data such as NMR and HPLC results. Researchers requiring specific purity grades or larger quantities are encouraged to contact technical support or the sales team directly. Standard shipping conditions for research-grade organohalogen compounds apply; please review the shipping and delivery policy on the Aladdin website for regional specifics.
Frequently asked questions
What is 4-bromo-7-chloro-6-fluoro-1H-indazole used for in research?
4-Bromo-7-chloro-6-fluoro-1H-indazole is primarily used as a synthetic building block and intermediate in medicinal chemistry. Its C-4 bromine substituent enables palladium-catalyzed cross-coupling reactions such as Suzuki and Buchwald-Hartwig couplings, while the fluorine and chlorine substituents modulate electronic properties and provide additional sites for selective derivatization. It is relevant in kinase inhibitor programs, antiviral, and CNS drug discovery pipelines.
How should I store 4-bromo-7-chloro-6-fluoro-1H-indazole (SKU B175395) to maintain its purity?
Store the compound in a tightly sealed container in a cool, dry, and dark environment, away from moisture, strong oxidizers, and strong bases. It is recommended to keep the material under an inert atmosphere (nitrogen or argon) to prevent degradation. Always consult the Aladdin Scientific Safety Data Sheet (SDS) and Certificate of Analysis (CoA) for lot-specific storage recommendations.
What cross-coupling reactions are compatible with 4-bromo-7-chloro-6-fluoro-1H-indazole?
The C-4 bromine of this compound is well-suited for palladium-catalyzed cross-coupling reactions, including Suzuki-Miyaura (with boronic acids), Buchwald-Hartwig amination, Negishi coupling (with organozinc reagents), and Sonogashira coupling (with terminal alkynes). The C-7 chlorine can also participate in cross-coupling or nucleophilic aromatic substitution under appropriate conditions, offering orthogonal selectivity in multi-step synthesis.
Where can I find the Certificate of Analysis (CoA) and Safety Data Sheet (SDS) for B175395?
The Certificate of Analysis and Safety Data Sheet for 4-bromo-7-chloro-6-fluoro-1H-indazole (SKU B175395) are available on the Aladdin Scientific website at aladdin-e.com. Navigate to the product page for B175395 and download the documents directly, or contact Aladdin Scientific customer service for assistance.
Is 4-bromo-7-chloro-6-fluoro-1H-indazole available in bulk or custom quantities?
Yes, Aladdin Scientific can accommodate bulk and custom quantity requests for B175395. Researchers and procurement teams should contact the Aladdin Scientific sales team directly via the website or email to discuss pricing, lead times, and custom packaging options for larger orders.
References
- Textbook-level knowledge of indazole heterocycle chemistry and halogenated building blocks in medicinal chemistry. No specific literature citation available in source material.
- Aladdin Scientific product page for 4-bromo-7-chloro-6-fluoro-1H-indazole, SKU B175395. aladdin-e.com.
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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