| 8-Hydroxyquinoline[1] | |
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Quinolin-8-ol, 8-Quinolinol |
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Other names
1-azanaphthalene-8-ol, Fennosan H 30, hydroxybenzopyridine, hoxybenzopyridine, oxychinolin, oxyquinoline, phenopyridine, quinophenol, oxine |
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| Identifiers | |
| CAS number | 148-24-3 |
| PubChem | 1923 |
| ChemSpider | 1847 |
| UNII | 5UTX5635HP |
| KEGG | D05321 |
| ChEBI | CHEBI:48981 |
| ChEMBL | CHEMBL310555 |
| ATC code | G01,A01AB07 D08AH03 R02AA14 |
| Jmol-3D images | Image 1 Image 2 |
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| Properties | |
| Molecular formula | C9H7NO |
| Molar mass | 145.16 g/mol |
| Appearance | White crystalline needles |
| Density | 1.034 g/cm3 |
| Melting point |
76 °C, 349 K, 169 °F |
| Boiling point |
276 °C, 549 K, 529 °F |
| Hazards | |
| MSDS | External MSDS |
| Main hazards | flammable |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| 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 colorless compound is widely used commercially, although under a variety of names.[2][3]
Contents |
It is usually prepared from quinoline-8-sulfonic acid and from a Skraup synthesis from 2-aminophenol.[4]
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]
The complexes as well as the heterocycle itself exhibit antiseptic, disinfectant, and pesticide properties.[7][8] Its solution in alcohol is used as liquid bandages. It once was of interest as an anti-cancer drug.[9]
The reaction of 8-hydroxyquinoline with aluminium(III) [10] 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.[11]
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.
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