Chemical Structure and Properties

5-(4-Chlorophenyl)-1H-pyrrolo[2,3-b]pyridine belongs to the pyrrolopyridine family of bicyclic heterocycles, specifically built on the 7-azaindole framework. The compound consists of a pyridine ring fused with a pyrrole ring, with a 4-chlorophenyl substituent at the 5-position of the pyridine ring. This arrangement confers planar aromaticity across the bicyclic core and introduces a halogen handle at the pendant phenyl ring, enabling downstream functionalization via cross-coupling reactions.

The 7-azaindole (pyrrolo[2,3-b]pyridine) scaffold is well recognized in medicinal chemistry as a bioisostere of purines and indoles, allowing productive interactions with ATP-binding sites of protein kinases. The 4-chlorophenyl group at position 5 enhances lipophilicity and may modulate binding selectivity in target-based drug discovery programs.

Note: Specific physicochemical data (molecular weight, melting point, LogP, solubility) are not provided in the current source material and should be verified against the product certificate of analysis or a reliable chemical database before use.

Handling, Storage, and Safety Guidelines

Personal Protective Equipment (PPE): When handling 5-(4-Chlorophenyl)-1H-pyrrolo[2,3-b]pyridine, wear appropriate laboratory PPE including nitrile gloves, safety goggles, and a laboratory coat. Work in a well-ventilated area or fume hood to minimize inhalation exposure to fine particulates.

Storage: Store the compound in a tightly sealed container, away from light and moisture, at the temperature specified on the product label or certificate of analysis. Pyrrolopyridine derivatives are generally stable under recommended storage conditions, but long-term stability should be confirmed by periodic quality checks. Keep away from incompatible materials including strong oxidizing agents and strong acids.

Disposal: Dispose of this compound and contaminated materials in accordance with local institutional and governmental regulations for chemical waste. Do not dispose of down drains or in municipal waste streams.

Note: Specific GHS hazard classifications, signal words, and H/P statements for this compound are not available in the current source material. Users must consult the product Safety Data Sheet (SDS) before use.

Laboratory Applications in Medicinal Chemistry

The pyrrolo[2,3-b]pyridine (7-azaindole) scaffold is a privileged structure in kinase inhibitor discovery. Compounds built on this core have been reported to inhibit a range of therapeutically relevant kinases by occupying the ATP-binding pocket, exploiting key hydrogen-bond interactions with the kinase hinge region through the NH of the pyrrole and the ring nitrogen of the pyridine.

5-(4-Chlorophenyl)-1H-pyrrolo[2,3-b]pyridine serves primarily as a synthetic building block or reference compound for structure–activity relationship (SAR) studies. The 4-chlorophenyl group at position 5 offers a handle for Suzuki–Miyaura, Negishi, or other palladium-catalyzed cross-coupling reactions, while the pyrrole NH can be protected or alkylated as required by the synthetic route. Researchers may use this compound to explore selectivity among kinase families, or as a starting point for elaboration into more complex drug candidates.

Beyond kinase biology, pyrrolopyridine derivatives have been explored in CNS drug discovery and as ligands for other enzyme classes. The rigid bicyclic aromatic framework facilitates predictable binding geometry, making it attractive for fragment-based drug design (FBDD) approaches.

Note: Specific biological activity data, IC50 values, or in vivo results for this exact compound are not available in the source material and must not be assumed without independent verification.

Ordering and Quality Information

5-(4-Chlorophenyl)-1H-pyrrolo[2,3-b]pyridine is available from Aladdin Scientific under catalog number H734299. When placing an order, please reference this SKU to ensure correct product identification. Researchers should request the current certificate of analysis (CoA) to confirm purity, identity (NMR, HPLC, or MS data), and batch-specific physicochemical data prior to use in sensitive assays.

For bulk quantities, custom synthesis inquiries, or technical support regarding this compound, please contact Aladdin Scientific's customer service team. All products are subject to Aladdin's standard quality control procedures and are intended for research use only; they are not approved for diagnostic, therapeutic, or food-additive applications.

Procurement teams should note that availability, pack sizes, and pricing may vary; consult the current Aladdin Scientific catalog or website for up-to-date information.