2-Chloro-4-methyl-5,6-dihydro-7H-cyclopenta[b]pyridin-7-one FAQ
2-Chloro-4-methyl-5,6-dihydro-7H-cyclopenta[b]pyridin-7-one FAQ
2-Chloro-4-methyl-5,6-dihydro-7H-cyclopenta[b]pyridin-7-one is a bicyclic heteroaromatic ketone serving as a versatile electrophilic building block for the synthesis of functionalized cyclopenta-fused pyridine scaffolds in medicinal and synthetic chemistry.
- Chemical Name
- 2-Chloro-4-methyl-5,6-dihydro-7H-cyclopenta[b]pyridin-7-one
- SKU / Catalog Number
- C194861
- Compound Class
- Bicyclic heteroaromatic ketone; cyclopenta[b]pyridinone derivative
- Key Functional Groups
- Aromatic C–Cl bond, cyclopentanone ring, pyridine ring, methyl substituent
- Primary Use
- Synthetic intermediate and electrophilic building block for heterocyclic scaffold construction
- Supplier
- Aladdin Scientific (SKU: C194861)
What Is 2-Chloro-4-methyl-5,6-dihydro-7H-cyclopenta[b]pyridin-7-one?
2-Chloro-4-methyl-5,6-dihydro-7H-cyclopenta[b]pyridin-7-one is a bicyclic compound in which a cyclopentanone ring is fused to a pyridine ring at the [b] bond. The molecule carries a chlorine substituent at position 2 and a methyl group at position 4 of the pyridine ring, while the carbonyl function resides at position 7 of the partially saturated cyclopentane ring. This combination of a reactive aryl chloride, a ketone, and a nitrogen-containing aromatic ring makes the compound a multifunctional scaffold for further chemical transformations.
The aryl C–Cl bond is amenable to nucleophilic aromatic substitution (SNAr) and transition-metal-catalyzed cross-coupling reactions (e.g., Suzuki, Buchwald–Hartwig, Negishi), enabling rapid diversification of the core structure. The ketone functionality can undergo condensation, reductive amination, or enolization chemistry, providing additional handles for library synthesis.
Physical and Chemical Properties
2-Chloro-4-methyl-5,6-dihydro-7H-cyclopenta[b]pyridin-7-one is a solid heterocyclic compound at ambient temperature. Its molecular formula is C9H8ClNO and it possesses a molecular weight of approximately 181.62 g/mol. The fused bicyclic architecture confers a degree of planarity to the pyridine portion of the molecule, while the cyclopentanone ring introduces conformational constraint. The pyridine ring nitrogen and the carbonyl oxygen provide hydrogen-bond acceptor capability, which is relevant for both solubility profiling and target-binding assessments in drug discovery contexts.
Common laboratory solvents such as dichloromethane, dimethyl sulfoxide (DMSO), dimethylformamide (DMF), and ethyl acetate are generally suitable for dissolving this class of compound. Specific solubility data should be verified experimentally for each application. Users should consult the Certificate of Analysis (CoA) supplied with each lot for purity, melting point, and spectroscopic confirmation data.
Handling, Storage, and Safety
As with most chlorinated heterocyclic compounds, appropriate laboratory precautions should be observed when handling 2-Chloro-4-methyl-5,6-dihydro-7H-cyclopenta[b]pyridin-7-one. Wear suitable personal protective equipment (PPE) including laboratory coat, nitrile gloves, and safety glasses. Work in a well-ventilated area or fume hood to minimize inhalation of dust or vapors.
For long-term storage, keep the compound in a tightly sealed container away from moisture, light, and heat. Storage under inert atmosphere (nitrogen or argon) at 2–8 °C or at room temperature (as specified on the product label and CoA) is generally recommended for chlorinated pyridinone building blocks to preserve purity and stability. Always consult the Safety Data Sheet (SDS) provided by Aladdin Scientific for definitive hazard classification, first-aid measures, and disposal guidance.
Applications in Synthetic and Medicinal Chemistry
Cyclopenta[b]pyridinone scaffolds are of broad interest in medicinal chemistry because the fused ring system provides a rigid, three-dimensionally defined framework that can project substituents in defined vectors relative to a biological target. The 2-chloro substituent makes this particular compound an ideal precursor for SNAr reactions with amines, thiols, or alkoxides, as well as a partner in palladium-catalyzed coupling reactions to introduce aryl, heteroaryl, or alkyl groups.
Potential application areas include the preparation of kinase inhibitor candidates, GPCR ligands, and other bioactive small molecules that incorporate fused bicyclic pyridine cores. The methyl group at position 4 provides steric and electronic modulation of the pyridine ring, which can influence binding affinity and metabolic stability of derived compounds. Researchers in fragment-based drug discovery may also employ this compound as a fragment hit for elaboration.
Ordering and Availability from Aladdin Scientific
2-Chloro-4-methyl-5,6-dihydro-7H-cyclopenta[b]pyridin-7-one is available from Aladdin Scientific under catalog number C194861. To place an order, visit the Aladdin Scientific website and search by the SKU or the IUPAC name. Quantity options, current pricing, and lead times are displayed on the product page and may vary by region.
For bulk or custom quantities, please contact Aladdin Scientific's technical sales team directly. A Certificate of Analysis (CoA) and Safety Data Sheet (SDS) are available for each lot upon request or via the product page. If you require additional characterization data (e.g., NMR spectra, HPLC traces), please contact customer support prior to ordering.
Frequently asked questions
What is the molecular formula and molecular weight of 2-Chloro-4-methyl-5,6-dihydro-7H-cyclopenta[b]pyridin-7-one?
The molecular formula of 2-Chloro-4-methyl-5,6-dihydro-7H-cyclopenta[b]pyridin-7-one is C9H8ClNO, giving a molecular weight of approximately 181.62 g/mol. Please verify the exact value against the Certificate of Analysis (CoA) supplied with your specific lot from Aladdin Scientific (SKU: C194861).
What types of chemical reactions can be performed on this compound?
The compound offers multiple reactive sites: the aryl C–Cl bond at position 2 is suitable for nucleophilic aromatic substitution (SNAr) with nitrogen, oxygen, or sulfur nucleophiles, and for palladium-catalyzed cross-coupling reactions such as Suzuki–Miyaura, Buchwald–Hartwig amination, or Negishi coupling. The ketone at position 7 can undergo condensation, reductive amination, or Wittig-type reactions, providing additional diversification opportunities.
How should I store 2-Chloro-4-methyl-5,6-dihydro-7H-cyclopenta[b]pyridin-7-one to maintain its stability?
Store the compound in a tightly sealed container, protected from moisture, light, and heat. An inert atmosphere (nitrogen or argon) is recommended for long-term storage. Refer to the product label and the Aladdin Scientific Safety Data Sheet (SDS) for the lot-specific recommended storage temperature, as conditions may be specified as 2–8 °C or room temperature depending on the lot.
Is this compound suitable for use as a fragment in fragment-based drug discovery (FBDD)?
The bicyclic cyclopenta[b]pyridinone core of this compound has a low molecular weight and defined three-dimensional character, attributes that are generally valued in fragment-based drug discovery. The reactive chloro and ketone handles also make it amenable to rapid fragment elaboration. However, suitability for a specific FBDD campaign depends on the target of interest, physicochemical profiling, and experimental screening results.
How do I obtain a Certificate of Analysis (CoA) or Safety Data Sheet (SDS) for SKU C194861?
The Certificate of Analysis and Safety Data Sheet for 2-Chloro-4-methyl-5,6-dihydro-7H-cyclopenta[b]pyridin-7-one (SKU: C194861) are available through the Aladdin Scientific product page or by contacting Aladdin Scientific customer support directly. When requesting a CoA, please provide your lot number to ensure you receive the document corresponding to your specific batch.
References
- Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed.; Oxford University Press: Oxford, 2012. (General reference for SNAr and cross-coupling reaction types applicable to aryl chloride building blocks.)
- 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. doi:10.1021/jm200187y
- Erlanson, D. A.; Fesik, S. W.; Hubbard, R. E.; Jahnke, W.; Jhoti, H. Twenty years on: the impact of fragments on drug discovery. Nat. Rev. Drug Discov. 2016, 15, 605–619. doi:10.1038/nrd.2016.109
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