Oxyquinoline

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
CAS Number	148-24-3^Y
3D model (Jmol)	Interactive image Interactive image
ChEBI	CHEBI:48981^Y
ChEMBL	ChEMBL310555^Y
ChemSpider	1847^Y
ECHA InfoCard	100.005.193
KEGG	D05321^Y
PubChem	1923
UNII	5UTX5635HP^Y
InChI InChI=1S/C9H7NO/c11-8-5-1-3-7-4-2-6-10-9(7)8/h1-6,11H^Y Key: MCJGNVYPOGVAJF-UHFFFAOYSA-N^Y InChI=1/C9H7NO/c11-8-5-1-3-7-4-2-6-10-9(7)8/h1-6,11H Key: MCJGNVYPOGVAJF-UHFFFAOYAG
SMILES Oc1cccc2cccnc12 c1cc2cccnc2c(c1)O
Properties
Chemical formula	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
ATC code	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).
Y (what is ^YN ?)
Infobox references

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.

It is usually prepared from quinoline-8-sulfonic acid and from Skraup synthesis from 2-aminophenol.

8-Hydroxyquinoline is a monoprotic bidentate chelating agent. In neutral solution, the hydroxyl is in the protonated form (pK_a=9.89) and the nitrogen is not protonated (pK_a=5.13). 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).

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

The reaction of 8-hydroxyquinoline with aluminium(III) results in Alq₃, a common component of organic light-emitting diodes (OLEDs). Variations in the substituents on the quinoline rings affect its luminescence properties.

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.

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Wikipedia