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8-Hyydroxyquinoline
Introduction
Overview
Overview
8-Hydroxyquinoline is an organic compound with the formula C9H7NO. It is a derivative of the heterocycle quinoline by placement of an OH group on carbon number 8. This light yellow compound is widely used commercially, although under a variety of names.[2][3]
Synthesis
Synthesis
It is usually prepared from quinoline-8-sulfonic acid and from a Skraup synthesis from 2-aminophenol.[4]
As a chelating agent
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. In neutral solution, the hydroxyl is in the protonated form (pKa=9.89) and the nitrogen is not protonated (pKa=5.13).[5] However, an excited-state zwitterionic isomer exists in which H+ is transferred from the oxygen (giving an oxygen anion) to the nitrogen (giving a protonated nitrogen cation).[6]
Applications
Applications
The complexes as well as the heterocycle itself exhibit antiseptic, disinfectant, and pesticide properties,[7][8] functioning as a transcription inhibitor.[9] Its solution in alcohol is used as liquid bandages. It once was of interest as an anti-cancer drug.[10]
The reaction of 8-hydroxyquinoline with aluminium(III)[11] results in Alq3, a common component of organic light-emitting diodes (OLED’s). Variations in the substituents on the quinoline rings affect its luminescence properties.[12]
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.
Hydroxyquinoline was used as a stabilizer of hydrogen peroxide in a rocket fuel oxidizer (T-Stoff) for the German Messerschmitt Me 163 Komet in World War 2.
References
References
- β Nanjing Odyssey Chemicals
- β “8-Hydroxyquinoline Safety Data”. Oxford University.
- β “8-Hydroxyquinoline”. PAN Pesticides Database.
- β Collin, G.; HΓΆke, H. (2005). “Quinoline and Isoquinoline”. Ullmann’s Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_465.
- β Template:Cite doi
- β Template:Cite doi
- β Phillips, J. P. (1956). “The Reactions of 8-Quinolinol”. Chemical Reviews. 56 (2): 271β297. doi:10.1021/cr50008a003.
- β “8-Hydroxyquinoline”. Medical Dictionary Online.
- β “8-Hydroxyquinoline”. Sigma-Aldrich. Retrieved 2012-05-23.
- β Shen, A. Y.; Wu, S. N.; Chiu, C. T. (1999). “Synthesis and Cytotoxicity Evaluation of some 8-Hydroxyquinoline Derivatives”. Journal of Pharmacy and Pharmacology. 51 (5): 543β548. doi:10.1211/0022357991772826. PMIDΒ 10411213.
- β Katakura, R.; Koide, Y. (2006). “Configuration-Specific Synthesis of the Facial and Meridional Isomers of Tris(8-hydroxyquinolinate)aluminum (Alq3)”. Inorganic Chemistry. 45 (15): 5730β5732. doi:10.1021/ic060594s.
- β Montes, V. A.; Pohl, R.; Shinar, J.; Anzenbacher, P. Jr. (2006). “Effective Manipulation of the Electronic Effects and Its Influence on the Emission of 5-Substituted Tris(8-quinolinolate) Aluminum(III) Complexes”. Chemistry – A European Journal. 12 (17): 4523β4535. doi:10.1002/chem.200501403.
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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]