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Quinoline is a heterocyclic aromatic organic compound with the chemical formula C9H7N. It is a colorless hygroscopic liquid with a strong odor. Aged samples, especially if exposed to light, become yellow and later brown. Quinoline is only slightly soluble in cold water but dissolves readily in hot water and most organic solvents. Quinoline itself has few applications, but many of its derivatives are useful in diverse applications. A prominent example is quinine, an alkaloid found in plants. Over 200 biologically active quinoline and quinazoline alkaloids are identified. 4-Hydroxy-2-alkylquinolines (HAQs) are involved in antibiotic resistance.
Like other nitrogen heterocyclic compounds, such as pyridine derivatives, quinoline is often reported as an environmental contaminant associated with facilities processing oil shale or coal, and has also been found at legacy wood treatment sites. Owing to its relatively high solubility in water quinoline has significant potential for mobility in the environment, which may promote water contamination. Quinoline is readily degradable by certain microorganisms, such as Rhodococcus species Strain Q1, which was isolated from soil and paper mill sludge.
Quinolines are present in small amounts in crude oil within the virgin diesel fuel fraction. It can be removed by the process called hydrodenitrification.
A number of other processes exist, which require specifically substituted anilines or related compounds:
Quinolines are reduced to tetrahydroquinolines enantioselectively using several catalyst systems.Xu, L.; Lam, K. H.; Ji, J.; Wu, J.; Fan, Q.-H.; Lo, W.-H.; Chan, A. S. C. Chem. Commun. 2005, 1390.Reetz, M. T.; Li, X. Chem. Commun. 2006, 2159.
Quinoline is mainly used as in the production of other specialty chemicals. Approximately 4 were produced annually according to a report published in 2005. Its principal use is as a precursor to 8-hydroxyquinoline, which is a versatile chelating agent and precursor to pesticides. Its quinaldine and lepidine derivatives are precursors to . Oxidation of quinoline affords quinolinic acid (pyridine-2,3-dicarboxylic acid), a precursor to the herbicide sold under the name "Assert".
The reduction of quinoline with sodium borohydride in the presence of acetic acid is known to produce Kairoline A. (Cf. Kairine)
Several anti-malarial drugs contain quinoline substituents. These include quinine, chloroquine, amodiaquine, and primaquine.
Quinoline is used as a solvent and reagent in organic synthesis.
Quinolinium compounds (e.g. salts) can also be used as corrosion inhibitors and intensifiers.
(2025). 9780470842898 ISBN 9780470842898
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