5-Chloro-6-methylpyridin-3-ol: Properties & Research Uses
5-Chloro-6-methylpyridin-3-ol: Properties & Research Uses
5-Chloro-6-methylpyridin-3-ol is a halogenated hydroxypyridine building block valued in medicinal chemistry and heterocyclic synthesis for its multifunctional reactive sites.
- IUPAC Name
- 5-Chloro-6-methylpyridin-3-ol
- SKU
- C193721
- Molecular Formula
- C₆H₆ClNO
- Molecular Weight
- 143.57 g/mol
- Compound Class
- Halogenated hydroxypyridine
- Key Functional Groups
- Hydroxyl (–OH), Chloro (–Cl), Methyl (–CH₃) on pyridine ring
Chemical Structure and Key Properties
5-Chloro-6-methylpyridin-3-ol (molecular formula C₆H₆ClNO, MW ≈ 143.57 g/mol) belongs to the hydroxypyridine family of heterocyclic compounds. The molecule features a six-membered pyridine ring substituted at position 3 with a hydroxyl group, position 5 with a chlorine atom, and position 6 with a methyl group. This combination of substituents creates a compound with distinct electronic and steric characteristics.
The hydroxyl group at the 3-position can participate in hydrogen bonding, influencing solubility and crystal packing, while the electron-withdrawing chlorine at position 5 modulates the ring's electron density and reactivity. The methyl group at position 6 introduces steric effects adjacent to the ring nitrogen, which can be leveraged in selective functionalization strategies. Together, these features make 5-Chloro-6-methylpyridin-3-ol a versatile scaffold for further chemical elaboration.
Synthesis Relevance and Reactivity
As a multifunctional pyridine intermediate, 5-Chloro-6-methylpyridin-3-ol offers several handles for synthetic elaboration. The aryl chloride at position 5 is amenable to palladium-catalyzed cross-coupling reactions such as Suzuki–Miyaura, Negishi, and Buchwald–Hartwig amination, enabling the introduction of aryl, alkyl, or amino substituents with high selectivity. These transformations are central to modern medicinal chemistry workflows aimed at building structural diversity around a heterocyclic core.
The phenolic hydroxyl group can be O-alkylated, acylated, or converted to a triflate for further nucleophilic substitution or cross-coupling. The methyl group at position 6 can, under appropriate oxidative conditions, be converted to a carboxylic acid or aldehyde, extending the synthetic utility of this building block. The cumulative reactivity profile positions this compound as a valuable intermediate in multi-step synthesis programs.
Research and Pharmaceutical Applications
Hydroxypyridine derivatives bearing halogen and alkyl substituents are widely encountered as key intermediates in the discovery and development of bioactive molecules. The structural motif present in 5-Chloro-6-methylpyridin-3-ol is relevant to the design of enzyme inhibitors, receptor ligands, and agrochemical active ingredients, where the pyridine ring serves as a bioisostere for benzene while providing improved water solubility and metabolic stability.
Researchers working in target-based drug discovery may employ this compound as a starting material or advanced intermediate for the construction of compound libraries intended for high-throughput screening. Its defined substitution pattern allows medicinal chemists to systematically explore structure–activity relationships (SAR) around the pyridinol scaffold. Additionally, the compound may serve as a reference standard or analytical reagent in assay development and method validation workflows.
Handling, Storage, and Safety Considerations
As with most halogenated organic intermediates, 5-Chloro-6-methylpyridin-3-ol should be handled with standard laboratory precautions. Personnel should wear appropriate personal protective equipment including chemical-resistant gloves, safety glasses, and a laboratory coat. Operations that may generate dust or aerosols should be performed in a well-ventilated fume hood.
For storage, the compound should be kept in a tightly sealed container away from moisture, heat, and incompatible materials such as strong oxidizing agents and strong bases. Storing at cool, dry conditions (typically 2–8 °C or as specified on the product label) is recommended to maintain long-term stability and purity. Researchers should consult the Safety Data Sheet (SDS) provided by Aladdin Scientific for comprehensive hazard information, first-aid measures, and disposal guidance specific to this product (SKU C193721) prior to use.
Frequently asked questions
What is 5-Chloro-6-methylpyridin-3-ol used for in research?
5-Chloro-6-methylpyridin-3-ol is primarily used as a synthetic building block and intermediate in medicinal chemistry, heterocyclic synthesis, and agrochemical research. Its multiple reactive sites—aryl chloride, phenolic hydroxyl, and methyl group—allow chemists to construct structurally diverse libraries for SAR studies and drug discovery programs.
What cross-coupling reactions are compatible with 5-Chloro-6-methylpyridin-3-ol?
The aryl chloride at position 5 is compatible with palladium-catalyzed cross-coupling reactions including Suzuki–Miyaura (with boronic acids), Negishi (with organozinc reagents), and Buchwald–Hartwig amination (with amines). Reaction conditions should be optimized with respect to catalyst loading, ligand choice, and base to account for the electronic environment of the pyridine ring.
How should I store 5-Chloro-6-methylpyridin-3-ol to maintain its stability?
The compound should be stored in a tightly sealed container under cool, dry conditions, typically at 2–8 °C, and protected from moisture and light. Always refer to the product SDS and the certificate of analysis (CoA) provided by Aladdin Scientific for the most authoritative storage and stability information specific to lot C193721.
What is the molecular formula and molecular weight of 5-Chloro-6-methylpyridin-3-ol?
5-Chloro-6-methylpyridin-3-ol has the molecular formula C₆H₆ClNO and a molecular weight of approximately 143.57 g/mol. These values are consistent with the substitution pattern of a chloro, methyl, and hydroxyl group on the pyridine ring.
References
- Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed.; Oxford University Press: Oxford, 2012. (General reference for pyridine chemistry and cross-coupling reactions.)
- Joule, J. A.; Mills, K. Heterocyclic Chemistry, 5th ed.; Wiley-Blackwell: Chichester, 2010. (Reference for hydroxypyridine reactivity and synthetic utility.)
- Aladdin Scientific. Product Data Sheet: 5-Chloro-6-methylpyridin-3-ol, SKU C193721. Aladdin Scientific, Shanghai.
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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