Isoquinoline
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| Names | |||
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Preferred IUPAC name
Isoquinoline
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| Other names
Benzo[c]pyridine
2-benzanine |
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3D model (Jmol)
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| DrugBank | |||
| ECHA InfoCard | 100.003.947 | ||
| EC Number | 204-341-8 | ||
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PubChem CID
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| Properties | |||
| C9H7N | |||
| Molar mass | 129.16 g·mol−1 | ||
| Appearance | yellowish oily liquid, hygroscopic platelets when solid | ||
| Density | 1.099 g/cm3 | ||
| Melting point | 26 to 28 °C (79 to 82 °F; 299 to 301 K) | ||
| Boiling point | 242 °C (468 °F; 515 K) | ||
| Acidity (pKa) | pKBH+=5.14 | ||
| -83.9·10−6 cm3/mol | |||
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 (what is   ?) |
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| Infobox references | |||
Isoquinoline is a heterocyclic aromatic organic compound. It is a structural isomer of quinoline. Isoquinoline and quinoline are benzopyridines, which are composed of a benzene ring fused to a pyridine ring. In a broader sense, the term isoquinoline is used to make reference to isoquinoline derivatives. 1-Benzylisoquinoline is the structural backbone in naturally occurring alkaloids including papaverine. The isoquinoline ring in these natural compound derives from the aromatic amino acid tyrosine.
Isoquinoline is a colorless hygroscopic liquid at room temperature with a penetrating, unpleasant odor. Impure samples can appear brownish, as is typical for nitrogen heterocycles. It crystallizes platelets that have a low solubility in water but dissolve well in ethanol, acetone, diethyl ether, carbon disulfide, and other common organic solvents. It is also soluble in dilute acids as the protonated derivative.
Being an analog of pyridine, isoquinoline is a weak base, with a pKa of 5.14. It protonates to form salts upon treatment with strong acids, such as HCl. It forms adducts with Lewis acids, such as BF3.
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