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8-Hydroxyquinoline
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	1923
SMILES	OC1=C(N=CC=C2)C2=CC=C1
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]

[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. 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]

[edit] 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.

[edit] 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:10.1039/JR9560001294. edit
^ 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:10.1021/jp971293u. edit
^ 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:10.1211/0022357991772826. 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

[0] Nanjing Odyssey Chemicals

[multiple-1] Oxford University 8-hydroxyquinoline Safety Data

[2] Pesticide Database

[3] Gerd Collin, Hartmut Höke "Quinoline and Isoquinoline" Ullmann's Encyclopedia of Chemical Technology; 2005 Wiley-VCH, Weinheim.10.1002/14356007.a22 465

[4] 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:10.1039/JR9560001294. edit

[5] 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:10.1021/jp971293u. edit

[6] Phillips, J. P. “The Reactions Of 8-Quinolinol” Chemical Reviews 1956, volume 56, pp 271 - 297; DOI: 10.1021/cr50008a003

[7] Medical Dictionary Online

[8] Shen AY, Wu SN, Chiu CT (1999). "Synthesis and cytotoxicity evaluation of some 8-hydroxyquinoline derivatives". J. Pharm. Pharmacol. 51 (5): 543–8. doi:10.1211/0022357991772826. PMID 10411213.

[9] 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

[10] 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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Contents

[edit] Synthesis

[edit] As a chelating agent

[edit] Applications

[edit] References