8-Hydroxyquinoline

8-Hydroxyquinoline is an organic compound with the formula C₉H₆NOH. It is a derivative of the heterocycle quinoline by placement of an OH group on carbon number 8. This colorless compound is widely used commercially, although under a variety of names.^[2][3]

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Synthesis

It is usually prepared from quinoline-8-sulfonic acid and from a Skraup synthesis from 2-aminophenol.^[4]

As a chelating agent

8-Hydroxyquinoline is a monoprotic bidentate chelating agent. Related ligands are the Schiff bases derived from salicylaldehyde, such as salicylaldoxime and salen.

Applications

The complexes as well as the heterocycle itself exhibit antiseptic, disinfectant, and pesticide properties.^[5][6] Its solution in alcohol are used as liquid bandages. It once was of interest as an anti-cancer drug.^[7]

The roots of the invasive plant Centaurea diffusa release 8-hydroxyquinoline, which has a negative effect on plants that have not co-evolved with it.

Safety

See MSDS.^[2]

References

1. ^ Nanjing Odyssey Chemicals
2. ^ ^{a b} Oxford University 8-hydroxyquinoline Safety Data
3. ^ Pesticide Database
4. ^ Gerd Collin, Hartmut Höke "Quinoline and Isoquinoline" Ullmann's Encyclopedia of Chemical Technology; 2005 Wiley-VCH, Weinheim.10.1002/14356007.a22 465
5. ^ Phillips, J. P. “The Reactions Of 8-Quinolinol” Chemical Reviews 1956, volume 56, pp 271 - 297; DOI: 10.1021/cr50008a003
6. ^ Medical Dictionary Online
7. ^ Shen AY, Wu SN, Chiu CT (1999). "Synthesis and cytotoxicity evaluation of some 8-hydroxyquinoline derivatives". J. Pharm. Pharmacol. 51 (5): 543-8. PMID 10411213.