8-Hydroxyquinoline
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8-Hydroxyquinoline
| 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 light yellow compound is widely used commercially, although under a variety of names.[2][3]
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Contents
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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 transferred 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] functioning as a transcription inhibitor.[9] Its solution in alcohol is used as liquid bandages. It once was of interest as an anti-cancer drug.[10]
The reaction of 8-hydroxyquinoline with aluminium(III)[11] 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.[12]
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.
References
- ^ Nanjing Odyssey Chemicals
- ^ "8-Hydroxyquinoline Safety Data". Oxford University. http://ptcl.chem.ox.ac.uk/MSDS/HY/8-hydroxyquinoline.html.[dead link]
- ^ "8-Hydroxyquinoline". PAN Pesticides Database. http://www.pesticideinfo.org/Detail_Chemical.jsp?Rec_Id=PC35563.
- ^ Collin, G.; Höke, H. (2005). "Quinoline and Isoquinoline". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi: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) 1956: 1294–1304. doi:10.1039/JR9560001294.
- ^ 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 (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.
- ^ "8-Hydroxyquinoline". Medical Dictionary Online. http://www.online-medical-dictionary.org/8-Hydroxyquinoline.asp?q=8-Hydroxyquinoline.
- ^ "8-Hydroxyquinoline". Sigma-Aldrich. http://www.sigmaaldrich.com/catalog/ProductDetail.do?D7=0&N5=SEARCH_CONCAT_PNO%7CBRAND_KEY&N4=H6878%7CSIAL&N25=0&QS=ON&F=SPEC. Retrieved 2012-05-23.
- ^ Shen, A. Y.; Wu, S. N.; Chiu, C. T. (1999). "Synthesis and Cytotoxicity Evaluation of some 8-Hydroxyquinoline Derivatives". Journal of Pharmacy and Pharmacology 51 (5): 543–548. doi:10.1211/0022357991772826. PMID 10411213.
- ^ Katakura, R.; Koide, Y. (2006). "Configuration-Specific Synthesis of the Facial and Meridional Isomers of Tris(8-hydroxyquinolinate)aluminum (Alq3)". Inorganic Chemistry 45 (15): 5730–5732. doi:10.1021/ic060594s.
- ^ 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:10.1002/chem.200501403.
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