8-Hydroxyquinoline

8-Hydroxyquinoline (aka oxine) is a chelating agent which has been used for the quantitative determination of metal ions.

Tris(8-hydroxyquinolinato)aluminium[1]
8-Hydroxyquinoline
Names
IUPAC name
Quinolin-8-ol, 8-Quinolinol
Other names
1-azanaphthalene-8-ol, Fennosan H 30, hydroxybenzopyridine, hoxybenzopyridine, oxychinolin, oxyquinoline, phenopyridine, quinophenol, oxine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.193
KEGG
UNII
Properties
C9H7NO
Molar mass 145.16 g/mol
Appearance White crystalline needles
Density 1.034 g/cm3
Melting point 76 °C (169 °F; 349 K)
Boiling point 276 °C (529 °F; 549 K)
Pharmacology
G01AC30 (WHO) A01AB07 (WHO) D08AH03 (WHO) R02AA14 (WHO)
Hazards
Main hazards flammable
Safety data sheet External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

In aqueous solution 8-hydroxyquinoline has a pKa value of ca. 9.9[2] It reacts with metal ions, losing the proton and forming 8-hydroxyquinolinato-chelate complexes.

The aluminium complex[3] is a common component of organic light-emitting diodes (OLEDs). Variations in the substituents on the quinoline rings affect its luminescence properties.[4]

In the photochemically induced excited-state zwitterionic isomers are formed in which the hydrogen atom is transferred from oxygen to nitrogen.[5]

The complexes as well as the heterocycle itself exhibit antiseptic, disinfectant, and pesticide properties,[6][7] functioning as a transcription inhibitor.[8] Its solution in alcohol is used in liquid bandages. It once was of interest as an anti-cancer drug.[9]

A thiol analogue, 8-mercaptoquinoline is also known.[10]

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.[11]


See also



References
  1. Cölle, M.; Dinnebier, R. E.; Brütting, W. (2002). "The structure of the blue luminescent δ-phase of tris(8-hydroxyquinoline)aluminium(III) (Alq3)". Chemical Communications. 2002 (23): 2908–9. doi:10.1039/b209164j. PMID 12478807.
  2. Albert, A.; Phillips, J. N. (1956). "264. Ionization Constants of Heterocyclic Substances. Part II. Hydroxy-Derivatives of Nitrogenous Six-Membered Ring-Compounds". Journal of the Chemical Society (Resumed). 1956: 1294–1304. doi:10.1039/JR9560001294.
  3. Katakura, R.; Koide, Y. (2006). "Configuration-Specific Synthesis of the Facial and Meridional Isomers of Tris(8-hydroxyquinolinate)aluminum (Alq3)". Inorganic Chemistry. 45 (15): 5730–5732. doi:10.1021/ic060594s. PMID 16841973.
  4. 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): 4523–4535. doi:10.1002/chem.200501403. PMID 16619313.
  5. Bardez, E.; Devol, I.; Larrey, B.; Valeur, B. (1997). "Excited-State Processes in 8-Hydroxyquinoline: Photoinduced Tautomerization and Solvation Effects". The Journal of Physical Chemistry B. 101 (39): 7786–7793. doi:10.1021/jp971293u.
  6. Phillips, J. P. (1956). "The Reactions of 8-Quinolinol". Chemical Reviews. 56 (2): 271–297. doi:10.1021/cr50008a003.
  7. "8-Hydroxyquinoline". Medical Dictionary Online. Archived from the original on 2016-10-09. Retrieved 2016-03-09.
  8. "8-Hydroxyquinoline". Sigma-Aldrich. Retrieved 2012-05-23.
  9. 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): 543–548. doi:10.1211/0022357991772826. PMID 10411213.
  10. Fleischer, Holger "Structural chemistry of complexes of (n - 1)d10nsm metal ions with β-N-donor substituted thiolate ligands (m=0, 2)" Coordination Chemistry Reviews 2005, volume 249, pp. 799-827. doi:10.1016/j.ccr.2004.08.024
  11. Vivanco, J.M.; Bais, H.P.; Stermitz, F.R.; Thelen, G.C.; Callaway, R.M. (2004). "Biogeographical variation in community response to root allelochemistry: novel weapons and exotic invasion". Ecology Letters. 7 (4): 285–292. doi:10.1111/j.1461-0248.2004.00576.x.
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