Quinoline

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Quinoline
IUPAC name Quinoline
Other names 1-benzazine, 1-azanaphthalene, benzo[b]pyridine
Identifiers
CAS number 91-22-5
SMILES c1cccc2cccnc12
Properties
Molecular formula C9H7N
Molar mass 129.16 g/mol
Density 1.093 g/ml
Melting point

−15 °C

Boiling point

238 °C

Solubility in water Soluble
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

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Overview

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.

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

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:

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