Quinoline_chemical_structure_part2.png

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Chemical formula	C9H7N
Molecular mass	129.16 g/mol
CAS number	*
Density	1.09 g/ml
Melting point	−15 °C
Boiling point	238 °C
SMILES	C1(N=CC=C2)=C2C=CC=C1
Chemical infobox

Quinoline, also known as 1-azanaphthalene, 1-benzazine, or benzo^*pyridine, is a heterocyclic aromatic organic compound. It has the formula C₉H₇N and is a colourless hygroscopic liquid with a strong odour.

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.

Isolation and synthesis

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Quinoline is naturally found in coal tar and was first extracted from this source in 1834 by F. Runge. It can be prepared using various methods:

• Conrad-Limpach synthesis using anilines and β-ketoesters.
• Doebner-Miller reaction using anilines and α,β-unsaturated carbonyl compounds.
• Friedländer synthesis using 2-aminobenzaldehyde and acetaldehyde.
• Skraup synthesis using ferrous sulfate, glycerol, aniline, nitrobenzene, and sulfuric acid.
• Povarov reaction using an aniline,a benzaldehyde and an activated alkene.

See also

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• 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.
• Indole, an analog with only a five-membered nitrogen ring.
• Simple aromatic rings

External links

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Nitrogen heterocycles | Solvents

Chinolin | Quinoléine | Chinolina | キノリン | Chinolina | Хинолин