1-(5-Chloropyridin-2-yl)piperazine: Properties & Lab Use
1-(5-Chloropyridin-2-yl)piperazine: Properties & Lab Use
1-(5-Chloropyridin-2-yl)piperazine is a chloropyridine-functionalized piperazine building block widely employed as a synthetic intermediate in medicinal chemistry and pharmaceutical research.
- Product Name
- 1-(5-Chloropyridin-2-yl)piperazine
- SKU
- C187427
- Molecular Formula
- C9H12ClN3
- Molecular Weight
- 197.66 g/mol
- Compound Class
- Chloropyridine-piperazine heterocyclic amine
- Primary Application
- Pharmaceutical intermediate and medicinal chemistry building block
Chemical Identity and Structure
1-(5-Chloropyridin-2-yl)piperazine (SKU: C187427) is an organic compound comprising a piperazine ring connected at its N-1 position to the 2-position of a 5-chloropyridine ring. Its molecular formula is C9H12ClN3 with a molecular weight of approximately 197.66 g/mol. The compound features two pharmacophoric motifs—the electron-deficient chloropyridine and the basic piperazine nitrogen—making it a versatile scaffold for drug discovery programs.
The presence of the chlorine substituent at the 5-position of the pyridine ring enhances the electrophilicity of the aromatic system, enabling downstream cross-coupling reactions such as Suzuki, Buchwald–Hartwig, and nucleophilic aromatic substitution, which are routine in medicinal chemistry workflows.
Applications in Medicinal Chemistry and Drug Discovery
The chloropyridinyl-piperazine motif found in 1-(5-Chloropyridin-2-yl)piperazine is a recurring structural element in CNS-active compounds, kinase inhibitors, and receptor modulators. Researchers use this building block to introduce a basic piperazine nitrogen alongside a heteroaromatic handle, enabling fine-tuning of lipophilicity, basicity (pKa), and binding affinity in lead optimization campaigns.
Common synthetic uses include: (1) N-acylation or N-sulfonylation of the free piperazine NH to generate amide or sulfonamide analogs; (2) palladium-catalyzed coupling at the aromatic C–Cl bond; and (3) incorporation into PROTAC linkers or fragment-based drug design libraries.
Handling, Storage, and Safety
As with all aromatic amine-containing compounds, appropriate laboratory precautions should be observed when working with 1-(5-Chloropyridin-2-yl)piperazine. Use personal protective equipment (PPE) including nitrile gloves, safety glasses, and a laboratory coat. Handle the compound in a well-ventilated fume hood to minimize inhalation of dust or vapors.
Storage recommendations for piperazine-based building blocks generally include keeping the material in a tightly sealed container, protected from moisture and light, at room temperature or under refrigeration (2–8 °C) depending on the specific lot stability data provided with the product. Users should consult the Safety Data Sheet (SDS) supplied by Aladdin Scientific for hazard classification, first-aid measures, and disposal procedures specific to this product.
Ordering and Product Specifications
1-(5-Chloropyridin-2-yl)piperazine is available from Aladdin Scientific under SKU C187427. Researchers and procurement teams may request purity certificates (CoA), Safety Data Sheets (SDS), and nuclear magnetic resonance (NMR) or HPLC purity data through the Aladdin Scientific product page or by contacting customer support directly.
For bulk quantities, custom synthesis inquiries, or specific purity grades (e.g., ≥95%, ≥98%), please reach out to the Aladdin Scientific sales team. Standard lead times and available pack sizes are listed on the product detail page, and volume pricing may be available for larger orders.
Frequently asked questions
What is 1-(5-Chloropyridin-2-yl)piperazine used for in research?
1-(5-Chloropyridin-2-yl)piperazine is primarily used as a synthetic building block in medicinal chemistry and pharmaceutical research. Its dual pharmacophoric character—combining an electron-deficient chloropyridine with a nucleophilic piperazine nitrogen—makes it valuable for constructing CNS drug candidates, kinase inhibitors, and receptor modulators via N-functionalization or palladium-catalyzed cross-coupling at the aryl chloride.
What is the molecular formula and molecular weight of 1-(5-Chloropyridin-2-yl)piperazine?
The molecular formula of 1-(5-Chloropyridin-2-yl)piperazine is C9H12ClN3, and its molecular weight is approximately 197.66 g/mol. These values reflect the combined mass of the five-membered piperazine ring, the chlorinated pyridine ring, and associated hydrogen atoms.
How should 1-(5-Chloropyridin-2-yl)piperazine be stored?
This compound should be stored in a tightly sealed container, away from moisture, heat, and direct light. Depending on the lot-specific stability data, storage at room temperature or under refrigeration (2–8 °C) may be recommended. Always consult the Aladdin Scientific Safety Data Sheet (SDS) and Certificate of Analysis (CoA) for the most accurate storage conditions for your specific lot.
What reactive transformations can be performed on 1-(5-Chloropyridin-2-yl)piperazine?
The compound offers two main sites for chemical elaboration: the free secondary piperazine NH, which can undergo N-acylation, N-sulfonylation, reductive amination, or alkylation; and the aryl C–Cl bond, which is amenable to palladium-catalyzed Suzuki coupling, Buchwald–Hartwig amination, and nucleophilic aromatic substitution reactions. This dual reactivity makes it a highly flexible intermediate for library synthesis.
How can I obtain a Certificate of Analysis or Safety Data Sheet for C187427?
Certificates of Analysis (CoA) and Safety Data Sheets (SDS) for 1-(5-Chloropyridin-2-yl)piperazine (C187427) are available through the Aladdin Scientific website product page or by contacting Aladdin Scientific customer support. Please have your lot number ready when requesting lot-specific documentation.
References
- March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 4th ed.; Wiley-Interscience: New York, 1992. General reference for nucleophilic aromatic substitution and N-functionalization chemistry.
- Roughley, S. D.; Jordan, A. M. The Medicinal Chemist's Toolbox: An Analysis of Reactions Used in the Pursuit of Drug Candidates. J. Med. Chem. 2011, 54, 3451–3479. Discusses prevalence of piperazine amide and cross-coupling reactions in drug discovery. doi:10.1021/jm200187y
- Aladdin Scientific product page for 1-(5-Chloropyridin-2-yl)piperazine, SKU C187427. For current pricing, purity, and availability, visit www.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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