8-Hydroxyquinoline
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| 8-Hydroxyquinoline[1] | |
|---|---|
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| IUPAC name | Quinolin-8-ol, 8-Quinolinol |
| Other names | 1-azanaphthalene-8-ol, Fennosan H 30, hydroxybenzopyridine, hoxybenzopyridine, oxychinolin, oxyquinoline, phenopyridine, quinophenol |
| Identifiers | |
| CAS number | [148-24-3] |
| PubChem | |
| SMILES | OC1=C(N=CC=C2)C2=CC=C1 |
| Properties | |
| Molecular formula | C9H7NO |
| Molar mass | 145.16 |
| 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 | |
| Main hazards | flammable |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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8-Hydroxyquinoline is an organic compound with the formula C9H7NOH. 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 |
[edit] Synthesis
It is usually prepared from quinoline-8-sulfonic acid and from a Skraup synthesis from 2-aminophenol.[4]
[edit] As a chelating agent
8-Hydroxyquinoline is a monoprotic bidentate chelating agent. Related ligands are the Schiff bases derived from salicylaldehyde, such as salicylaldoxime and salen.
[edit] Applications
The complexes as well as the heterocycle itself exhibit antiseptic, disinfectant, and pesticide properties.[5][6] Its solution in alcohol are used as liquid bandages. It once was of interest as an anti-cancer drug.[7]
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.
[edit] Safety
See MSDS.[2]
[edit] References
- ^ Nanjing Odyssey Chemicals
- ^ a b Oxford University 8-hydroxyquinoline Safety Data
- ^ Pesticide Database
- ^ Gerd Collin, Hartmut Höke "Quinoline and Isoquinoline" Ullmann's Encyclopedia of Chemical Technology; 2005 Wiley-VCH, Weinheim.10.1002/14356007.a22 465
- ^ Phillips, J. P. “The Reactions Of 8-Quinolinol” Chemical Reviews 1956, volume 56, pp 271 - 297; DOI: 10.1021/cr50008a003
- ^ Medical Dictionary Online
- ^ Shen AY, Wu SN, Chiu CT (1999). "Synthesis and cytotoxicity evaluation of some 8-hydroxyquinoline derivatives". J. Pharm. Pharmacol. 51 (5): 543–8. PMID 10411213.
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