| 8-Hydroxyquinoline[1] | |
|---|---|
 |
|
| 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 | 134-31-6 |
| PubChem | 1923 |
| SMILES |
Oc1cccc2cccnc12
|
| InChI |
1/C9H7NO/c11-8-5-1-3-7-4-2-6-10-9(7)8/h1-6,11H
|
| InChI key | MCJGNVYPOGVAJF-UHFFFAOYAG |
| ChemSpider ID | 1847 |
| 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 |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
| 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 |
Synthesis
It is usually prepared from quinoline-8-sulfonic acid and from a Skraup synthesis from 2-aminophenol.[4]
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. 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 transfered from the oxygen (giving an oxygen anion) to the nitrogen (giving a protonated nitrogen cation).[6]
Applications
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.
References
- ^ Nanjing Odyssey Chemicals
- ^ 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
- ^ 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): 1294. doi:.
- ^ 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: 7786. doi:.
- ^ 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. doi:. PMID 10411213.
- ^ Katakura, R.; Koide, Y. “Configuration-Specific Synthesis of the Facial and Meridional Isomers of Tris(8-hydroxyquinolinate)aluminum (Alq3)” Inorganic Chemistry 2006 volume 45,pp 5730-5732. doi:10.1021/ic060594s
- ^ Victor A. Montes, Radek Pohl, Joseph Shinar, Pavel Anzenbacher Jr. "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 2006, Volume 12, pp. p 4523-4535. doi:10.1002/chem.200501403
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