5-Bromo-1H-pyrazolo[3,4-c]pyridine: Properties & Lab FAQ

5-bromo-1H-pyrazolo[3,4-c]pyridine is a bicyclic nitrogen-rich heterocyclic compound featuring a bromine substituent at the 5-position, widely valued as a versatile synthetic building block and scaffold in medicinal chemistry and drug discovery research.

CAS Registry Number

Needs review — verify CAS for 5-bromo-1H-pyrazolo[3,4-c]pyridine

Molecular Formula

C6H4BrN3

Molecular Weight

198.02 g/mol

Core Scaffold

Pyrazolo[3,4-c]pyridine (azaindazole isomer)

Key Functional Handle

C–Br bond at position 5, amenable to cross-coupling reactions (Suzuki, Buchwald-Hartwig, etc.)

Aladdin SKU

B178266

Recommended Storage

Cool, dry, dark conditions; typically 2–8 °C or room temperature under inert atmosphere (verify with SDS)

Chemical Identity and Structure

5-Bromo-1H-pyrazolo[3,4-c]pyridine belongs to the pyrazolopyridine family of fused bicyclic heterocycles. The parent ring system, pyrazolo[3,4-c]pyridine, consists of a five-membered pyrazole ring fused to a pyridine ring in a [3,4-c] connectivity pattern, making it a structural isomer of the more common pyrazolo[3,4-b]pyridine and an analogue of azaindazoles. The bromine atom at the 5-position is located on the pyridine ring, providing a reactive electrophilic site for downstream synthetic transformations. The NH tautomer of the pyrazole ring is the predominant form in the solid state and in most common solvents. This scaffold incorporates three nitrogen atoms, imparting significant hydrogen-bond donor and acceptor capacity relevant to target engagement in biological systems.

Synthesis and Key Reactions

The C–Br bond at position 5 is the primary synthetic handle of this compound. Researchers routinely employ it in palladium-catalyzed cross-coupling reactions, including Suzuki–Miyaura coupling with aryl- or heteroarylboronic acids to install diverse carbon substituents, Buchwald–Hartwig amination to introduce amine functionalities, and Negishi or Stille couplings for carbon–carbon bond formation. The pyrazole NH can also participate in N-alkylation or N-arylation reactions, either as a competing site or as an intentional point of diversification after suitable protection strategies. Careful selection of base, solvent, and palladium ligand system is recommended to maximize selectivity, especially when both the C–Br and the pyrazole NH are present. The compound's planar aromatic character generally confers stability under standard Schlenk or inert-atmosphere cross-coupling conditions.

Solubility, Handling, and Storage

As a heteroaromatic solid, 5-bromo-1H-pyrazolo[3,4-c]pyridine exhibits moderate polarity. It is generally soluble in polar aprotic solvents such as DMSO, DMF, and NMP, and shows partial solubility in ethanol and methanol. Solubility in non-polar solvents such as hexane or diethyl ether is expected to be low. For biological assay stock solutions, DMSO is the recommended solvent; researchers should verify compound stability and solubility at working concentrations experimentally. The compound should be stored in a tightly sealed container under cool, dry, and dark conditions. Exposure to prolonged moisture or light should be avoided to prevent potential degradation of the heterocyclic core. Always consult the Safety Data Sheet (SDS) for specific handling precautions, personal protective equipment requirements, and waste disposal guidelines before use.

Applications in Medicinal Chemistry and Drug Discovery

The pyrazolo[3,4-c]pyridine scaffold is recognized as a privileged heterocyclic framework in drug discovery owing to its ability to mimic purine-like binding interactions, particularly relevant for ATP-competitive kinase inhibitor design. The three nitrogen atoms enable multiple hydrogen-bonding contacts with the hinge region of kinase active sites. The 5-bromo substituent serves as a versatile handle for library synthesis: parallel Suzuki coupling arrays can rapidly generate diverse analogues for structure–activity relationship (SAR) studies. Beyond kinase inhibition, pyrazolopyridine-containing compounds have been explored in the context of other enzyme targets and receptor modulation. The compact, drug-like molecular weight of 5-bromo-1H-pyrazolo[3,4-c]pyridine (approximately 198 g/mol) makes it an attractive fragment-sized starting point for fragment-based drug discovery (FBDD) campaigns as well as a conventional medicinal chemistry building block.

Ordering, Purity, and Quality Specifications

5-Bromo-1H-pyrazolo[3,4-c]pyridine is available from Aladdin Scientific under SKU B178266. Researchers should refer to the current product page or contact Aladdin's technical support team to obtain up-to-date information on available pack sizes, purity grades (typically ≥95% or ≥98% by HPLC for research-grade material), analytical certificates of analysis (CoA), and current pricing. Lot-specific CoA data including HPLC purity, NMR confirmation, and melting point (where available) can be requested at the time of order. For large-scale or GMP-adjacent procurement needs, please contact Aladdin's sales team directly to discuss custom quantities, additional analytical testing, or alternative grade options. Prompt delivery within standard Aladdin shipping timelines applies; consult the shipping and delivery policy for international orders involving controlled or regulated substances.

Frequently asked questions

What is the recommended solvent for preparing a stock solution of 5-bromo-1H-pyrazolo[3,4-c]pyridine for biological assays?

DMSO is the most commonly recommended solvent for preparing stock solutions of heteroaromatic compounds like 5-bromo-1H-pyrazolo[3,4-c]pyridine, owing to its broad solvating power and compatibility with most biochemical assays. Researchers should prepare a concentrated stock (e.g., 10–100 mM) and verify solubility and stability at the intended working concentration, since dilution into aqueous buffers may cause precipitation depending on the final DMSO percentage.

Can 5-bromo-1H-pyrazolo[3,4-c]pyridine be used directly in Suzuki–Miyaura cross-coupling reactions, and what conditions are typically required?

Yes, the C–Br bond at position 5 makes this compound a suitable electrophilic partner in Suzuki–Miyaura coupling with aryl- or heteroarylboronic acids or esters. Standard conditions typically involve a palladium source (e.g., Pd(PPh3)4 or Pd(dppf)Cl2), an inorganic base (e.g., K2CO3 or Cs2CO3), and a mixed aqueous-organic solvent system (e.g., dioxane/water or DMF/water) at elevated temperature (80–100 °C). The free pyrazole NH may require protection or careful base selection to avoid side reactions; pilot experiments are recommended.

How should 5-bromo-1H-pyrazolo[3,4-c]pyridine be stored to maintain stability and purity over time?

The compound should be stored in a tightly sealed vial under cool, dry, and dark conditions, ideally at 2–8 °C or as specified on the product label and SDS. Exposure to moisture, light, and air should be minimized, particularly after the container has been opened. For long-term storage, backfilling the headspace with an inert gas such as nitrogen or argon before resealing is advisable. Always check the lot-specific CoA and SDS provided by Aladdin Scientific for the most authoritative storage recommendations for each batch.

What makes the pyrazolo[3,4-c]pyridine scaffold particularly attractive for kinase inhibitor drug discovery?

The pyrazolo[3,4-c]pyridine scaffold geometrically and electronically mimics purine, allowing it to occupy the adenine-binding (hinge) region of kinase ATP pockets through complementary hydrogen-bonding interactions. Its three nitrogen atoms provide multiple hydrogen-bond donor and acceptor sites that can interact with conserved hinge residues of kinases. The scaffold's compact size and moderate lipophilicity contribute to favorable drug-like properties, and the 5-bromo handle enables rapid analogue synthesis for SAR exploration.

Is a Certificate of Analysis (CoA) available for B178266, and how can I request one?

Yes, Aladdin Scientific provides lot-specific Certificates of Analysis for its research reagents, including B178266. You can request a CoA by visiting the product page on the Aladdin website and entering your lot number, or by contacting Aladdin's customer service team directly via email or phone. The CoA typically includes HPLC purity data, NMR characterization, and other relevant analytical results specific to your batch.

References

1. Aladdin Scientific product page for 5-bromo-1H-pyrazolo[3,4-c]pyridine, SKU B178266. Retrieved from Aladdin Scientific official website.
2. General reference on pyrazolopyridine scaffolds in medicinal chemistry and kinase inhibitor design. Textbook-level knowledge; specific primary literature citation to be verified by editorial team.
3. General reference on Suzuki–Miyaura cross-coupling reactions with heteroaryl bromides. Textbook-level knowledge; specific primary literature citation to be verified by editorial team.

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