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Isoquinoline (C₉H₇N) is a heterocyclic aromatic compound and structural isomer of quinoline.
Structure: Comprises a benzene ring fused to a pyridine ring at the 3-4 bond.
Properties: Colorless, crystalline solid with a pungent odor; acts as a weak base. Moderately soluble in water.
Significance:
Core structure of numerous bioactive alkaloids (e.g., morphine, codeine, berberine, papaverine).
Found naturally (coal tar, plants) and synthesized for applications.
Uses:
Key building block in pharmaceuticals (analgesics, antifungals, anticancer drugs).
Precursor in organic synthesis (e.g., via Bischler-Napieralski reaction).
Used in dyes, antiseptics, and corrosion inhibitors.
Isoquinoline is a heterocyclic aromatic organic compound with the chemical formula C₉H₇N. It's structurally similar to quinoline but differs in the fusion position of its two rings. Here's a concise overview:
Structure:
Consists of a benzene ring fused to a pyridine ring at the 3-4 bond (unlike quinoline's 2-3 fusion).
This makes it an isomer of quinoline.
Acts as a weak base (pKa of conjugate acid ≈ 5.4).
Properties:
Colorless, hygroscopic solid at room temperature; turns yellow-brown with age.
Characteristic pungent, amine-like odor.
Moderately soluble in water, highly soluble in organic solvents.
Natural Occurrence & Significance:
Core scaffold of numerous biologically active alkaloids, including:
Papaverine (vasodilator)
Morphine & codeine (analgesics)
Berberine (antimicrobial)
Emetine (antiprotozoal)
Found in coal tar and as a pyrolysis product.
Synthetic Applications:
Key building block in pharmaceuticals (e.g., antipsychotics, antifungals, anticancer agents like trabectedin).
Used in dyes, agrochemicals, and ligands for catalysis.
Undergoes reactions like electrophilic substitution (prefers C-5/C-8), nucleophilic substitution, and reductions.
Key Reactions:
Bischler-Napieralski reaction: Synthesizes 3,4-dihydroisoquinolines (precursors to isoquinoline alkaloids).
Pomeranz-Fritsch reaction: Forms isoquinoline from benzaldehyde and aminoacetaldehyde diethyl acetal.
In summary: Isoquinoline is a vital nitrogen-containing heterocycle, fundamental to many natural alkaloids and synthetic pharmaceuticals, valued for its versatility in organic synthesis.
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