Chemistry:8-Hydroxyquinoline

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8-Hydroxyquinoline
Skeletal formula of 8-hydroxyquinoline
Ball-and-stick model of the 8-hydroxyquinoline molecule
8-hydroxyquinoline
Names
Preferred IUPAC name
Quinolin-8-ol
Other names
1-Azanaphthalene-8-ol, Fennosan H 30, Hydroxybenzopyridine, Oxybenzopyridine, Oxychinolin, Oxyquinoline, Phenopyridine, Quinophenol, Oxine, 8-Quinolinol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
UNII
Properties
C9H7NO
Molar mass 145.16 g/mol
Appearance White crystalline powder
Density 1.034 g/cm3
Melting point 76 °C (169 °F; 349 K)
Boiling point 276 °C (529 °F; 549 K)
Pharmacology
1=ATC code }} G01AC30 (WHO) A01AB07 (WHO) D08AH03 (WHO) R02AA14 (WHO)
Hazards
Safety data sheet External MSDS
GHS pictograms GHS06: ToxicGHS08: Health hazardGHS05: CorrosiveGHS09: Environmental hazard
GHS Signal word Danger
HH301Script error: No such module "Preview warning".Category:GHS errors, HH317Script error: No such module "Preview warning".Category:GHS errors, HH318Script error: No such module "Preview warning".Category:GHS errors, HH360DScript error: No such module "Preview warning".Category:GHS errors, HH410Script error: No such module "Preview warning".Category:GHS errors
PP202Script error: No such module "Preview warning".Category:GHS errors, PP273Script error: No such module "Preview warning".Category:GHS errors, PP280Script error: No such module "Preview warning".Category:GHS errors, PP301 + P310Script error: No such module "Preview warning".Category:GHS errors, PP302 + P352Script error: No such module "Preview warning".Category:GHS errors, PP305 + P351 + P338Script error: No such module "Preview warning".Category:GHS errors
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Tracking categories (test):

8-Hydroxyquinoline (also known as oxine) is an organic compound derived from the heterocycle quinoline. A colorless solid, its conjugate base is a chelating agent, which is used for the quantitative determination of metal ions.

In aqueous solution 8-hydroxyquinoline has a pKa value of ca. 9.9[1] It reacts with metal ions, losing the proton and forming 8-hydroxyquinolinato-chelate complexes.

Tris(8-hydroxyquinolinato)aluminium[2]

The aluminium complex,[3] is a common component of organic light-emitting diodes (OLEDs). Substituents on the quinoline ring affect the luminescence properties.[4]

In its photo-induced excited-state, 8-hydroxyquinoline converts to zwitterionic isomers, in which the hydrogen atom is transferred from oxygen to nitrogen.[5]

Bioactivity

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. ↑ 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. 
  2. ↑ 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. https://nbn-resolving.org/urn:nbn:de:bvb:384-opus4-679938. 
  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. http://www.online-medical-dictionary.org/definitions-8/8-hydroxyquinoline.html. 
  8. ↑ "8-Hydroxyquinoline". Sigma-Aldrich. http://www.sigmaaldrich.com/US/en/product/sial/h6878. 
  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, H. (2005). "Structural Chemistry of Complexes of (n-1)d10ns Metal Ions with β-N-Donor Substituted Thiolate Ligands (m=0, 2)". Coordination Chemistry Reviews 249 (7–8): 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. Bibcode: 2004EcolL...7..285V. 



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