Quinoline
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Quinoline, also known as 1-azanaphthalene, 1-benzazine, or benzo[b]pyridine, is a heterocyclic aromatic organic compound. It has the formula C9H7N and is a colourless hygroscopic liquid with a strong odour.
| Quinoline | |
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| Chemical name | Quinoline |
| Chemical formula | C9H7N |
| Molecular mass | 129.16 g/mol |
| Density | 1.09 g/ml |
| Melting point | -15 °C |
| Boiling point | 238 °C |
| CAS number | 91-22-5 |
| SMILES | C1(N=CC=C2)=C2C=CC=C1 |
| Missing image Quinoline_chemical_structure.png Chemical structure of quinoline | |
As it ages, if exposed to light, the liquid tends to become yellow and later brown. It is only slightly soluble in water but dissolves readily in many organic solvents.
Quinoline is an intermediate in metallurgical processes and in dye, polymer, and agrochemical production. It is also a preservative, disinfectant, and solvent.
It is toxic: short-term exposure to the vapour causes irritation of the nose, eyes, and throat as well as dizziness and nausea. Longer-term effects are uncertain, but quinoline has been linked to liver damage and is possibly carcinogenic and mutagenic.
As a Chemical
Quinoline is naturally found in coal tar and was first extracted from this source in 1834 by F. Runge. It can be prepared through the Skraup synthesis using ferrous sulfate, glycerol, aniline, nitrobenzene, and sulphuric acid. Other methods of synthesis are known, usually through a variant on aniline, glycerol and the acid but with different oxidizing agents. The reactions involved can be surprisingly violent.
See also
- Isoquinoline, an analog with the nitrogen atom in position 2.
- Pyridine, an analog without the fused benzene ring.
- Naphthalene, an analog without the nitrogen atom.
- Simple aromatic rings