What Is Hydroxyquinoline Used For?

eight-Hydroxyquinoline
Names



Preferred IUPAC name Quinolin-eight-ol
Other names 1-Azanaphthalene-8-ol, Fennosan H xxx, Hydroxybenzopyridine, Oxybenzopyridine, Oxychinolin, Oxyquinoline, Phenopyridine, Quinophenol, Oxine, 8-Quinolinol
Identifiers
CAS Number	148-24-iii ^Y
3D model (JSmol)	Interactive prototype Interactive image zwitterion: Interactive epitome
ChEBI	CHEBI:48981 ^Y
ChEMBL	ChEMBL310555 ^Y
ChemSpider	1847 ^Y
ECHA InfoCard	100.005.193
KEGG	D05321 ^Y
PubChem CID	1923
UNII	5UTX5635HP ^Y
CompTox Dashboard (EPA)	DTXSID5020730
InChI InChI=1S/C9H7NO/c11-8-five-1-iii-7-4-2-6-10-9(7)8/h1-half-dozen,11H^Y Fundamental: MCJGNVYPOGVAJF-UHFFFAOYSA-N^Y InChI=1/C9H7NO/c11-viii-5-one-3-7-4-two-half-dozen-10-nine(seven)8/h1-6,11H Key: MCJGNVYPOGVAJF-UHFFFAOYAG
SMILES Oc1cccc2cccnc12 c1cc2cccnc2c(c1)O zwitterion: c1cc2ccc[nH+]c2c(c1)[o-]
Properties
Chemical formula	C₉H₇NO
Molar mass	145.16 g/mol
Advent	White crystalline needles
Density	ane.034 k/cm³
Melting point	76 °C (169 °F; 349 Thousand)
Boiling point	276 °C (529 °F; 549 One thousand)
Pharmacology
ATC code	G01AC30 (WHO) A01AB07 (WHO) D08AH03 (WHO) R02AA14 (WHO)
Hazards
Occupational safe and wellness (OHS/OSH):
Primary hazards	flammable
Condom data sheet (SDS)	External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Yverify (what is^{Y N} ?) Infobox references

Chemic chemical compound

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

In aqueous solution eight-hydroxyquinoline has a pK_a value of ca. ix.ix^[i] It reacts with metallic ions, losing the proton and forming 8-hydroxyquinolinato-chelate complexes.

The aluminium complex^[2] is a common component of organic light-emitting diodes (OLEDs). Variations in the substituents on the quinoline rings affect its luminescence properties.^[3]

In the photochemically induced excited-land zwitterionic isomers are formed in which the hydrogen atom is transferred from oxygen to nitrogen.^[4]

The complexes as well as the heterocycle itself exhibit antiseptic, disinfectant, and pesticide properties,^[five] ^[6] functioning every bit a transcription inhibitor.^[vii] Its solution in booze is used in liquid bandages. Information technology one time was of interest equally an anti-cancer drug.^[viii]

A thiol analogue, 8-mercaptoquinoline is as well known.^[9]

The roots of the invasive institute Centaurea diffusa release 8-hydroxyquinoline, which has a negative effect on plants that have not co-evolved with information technology.^[10]

Run into too [edit]

Clioquinol, an antifungal drug and antiprotozoal drug.
PBT2
QUPIC
Ionophore
Trace metal detection test

References [edit]

^ Albert, A.; Phillips, J. Due north. (1956). "264. Ionization Constants of Heterocyclic Substances. Part Two. Hydroxy-Derivatives of Nitrogenous Vi-Membered Ring-Compounds". Journal of the Chemical Society (Resumed). 1956: 1294–1304. doi:10.1039/JR9560001294.
^ Katakura, R.; Koide, Y. (2006). "Configuration-Specific Synthesis of the Facial and Meridional Isomers of Tris(viii-hydroxyquinolinate)aluminum (Alq₃)". Inorganic Chemical science. 45 (15): 5730–5732. doi:10.1021/ic060594s. PMID 16841973.
^ 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:ten.1002/chem.200501403. PMID 16619313.
^ Bardez, E.; Devol, I.; Larrey, B.; Valeur, B. (1997). "Excited-Land Processes in 8-Hydroxyquinoline: Photoinduced Tautomerization and Solvation Effects". The Journal of Concrete Chemistry B. 101 (39): 7786–7793. doi:10.1021/jp971293u.
^ Phillips, J. P. (1956). "The Reactions of 8-Quinolinol". Chemical Reviews. 56 (2): 271–297. doi:10.1021/cr50008a003.
^ "viii-Hydroxyquinoline". Medical Dictionary Online. Archived from the original on 2016-x-09. Retrieved 2016-03-09 .
^ "8-Hydroxyquinoline". Sigma-Aldrich. Retrieved 2022-02-fifteen .
^ Shen, A. Y.; Wu, S. N.; Chiu, C. T. (1999). "Synthesis and Cytotoxicity Evaluation of some viii-Hydroxyquinoline Derivatives". Journal of Chemist's and Pharmacology. 51 (v): 543–548. doi:10.1211/0022357991772826. PMID 10411213. S2CID 33085238.
^ Fleischer, Holger "Structural chemical science of complexes of (n - 1)d¹⁰ns^k metal ions with β-N-donor substituted thiolate ligands (m=0, 2)" Coordination Chemistry Reviews 2005, book 249, pp. 799-827. doi:10.1016/j.ccr.2004.08.024
^ Vivanco, J.K.; Bais, H.P.; Stermitz, F.R.; Thelen, G.C.; Callaway, R.M. (2004). "Biogeographical variation in customs response to root allelochemistry: novel weapons and exotic invasion". Environmental Letters. 7 (4): 285–292. doi:ten.1111/j.1461-0248.2004.00576.ten.
^ Cölle, M.; Dinnebier, R. E.; Brütting, W. (2002). "The structure of the blueish luminescent δ-stage of tris(eight-hydroxyquinoline)aluminium(3) (Alq₃)". Chemical Communications. 2002 (23): 2908–9. doi:10.1039/b209164j. PMID 12478807.