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5-Chloro-2-fluoro-3-methylpyridine (C₆H₅ClFN; MW 145.56 g/mol) is a specialized heterocyclic building block in organic synthesis.
Structure: Pyridine ring with chloro (C5), fluoro (C2), and methyl (C3) substituents.
Reactivity:
C5–Cl: Electrophilic site for cross-coupling (e.g., Suzuki, Buchwald–Hartwig).
C2–F: Directs ortho-lithiation at C4/C6 for C–H functionalization.
C3–CH₃: Can be oxidized to aldehyde/carboxylic acid.
Applications:
Synthesizing pharmaceuticals (e.g., kinase inhibitors, antiviral agents).
Developing agrochemicals (herbicides, insecticides like neonicotinoid analogs).
Properties: Low water solubility; used in anhydrous reactions.
5-Chloro-2-fluoro-3-methylpyridine is a multifunctional heterocyclic compound with the molecular formula C₆H₅ClFN. Below is its key chemical profile:
Core: Pyridine ring (aromatic nitrogen heterocycle).
Substituents:
Chloro at position 5 (electrophile for cross-coupling).
Fluoro at position 2 (ortho-directing group for metallation).
Methyl at position 3 (electron-donating/stability modifier).
Molecular Weight: 145.56 g/mol.
Boiling Point: ~195–200°C (estimated).
Reactivity:
C5–Cl bond: Susceptible to Suzuki, Stille, or SNAr reactions.
C2–F bond: Activates ortho positions for lithiation/functionalization.
C3–CH₃: Can be oxidized to aldehyde/carboxylic acid.
Pharmaceuticals: Building block for kinase inhibitors, CNS agents.
Agrochemicals: Intermediate in pesticides/herbicides (e.g., flupyradifurone analogs).
Material Science: Ligand for catalysts or functional polymers.
Cross-coupling hub: Enables C–C, C–N, C–O bond formation.
Regioselective functionalization: Fluorine directs metalation at C4 or C6.
5-Chloro-2-fluoro-3-methylpyridine (C₆H₅ClFN, MW 145.56) is a triply substituted pyridine vital in medicinal/agro chemistry. Its chloro (C5), fluoro (C2), and methyl (C3) groups enable diverse reactions:
C5–Cl: Cross-couplings (e.g., Suzuki).
C2–F: Ortho-directing for lithiation/functionalization.
C3–CH₃: Oxidation to carboxylic derivatives.
Used to synthesize drug candidates (kinase inhibitors) and crop protection agents. The fluorine enhances bioavailability, while methyl aids stability.
For synthesis, commercial suppliers (e.g., Combi-Blocks, Enamine) offer this compound for R&D.
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