8-Hydroxyquinoline

8-Hydroxyquinoline[1]
Skeletal formula of 8-hydroxyquinoline
Ball-and-stick model of the 8-hydroxyquinoline molecule
Names
IUPAC name
Quinolin-8-ol, 8-Quinolinol
Other names
1-azanaphthalene-8-ol, Fennosan H 30, hydroxybenzopyridine, hoxybenzopyridine, oxychinolin, oxyquinoline, phenopyridine, quinophenol, oxine
Identifiers
148-24-3 YesY
ChEBI CHEBI:48981 YesY
ChEMBL ChEMBL310555 YesY
ChemSpider 1847 YesY
Jmol interactive 3D Image
Image
KEGG D05321 YesY
PubChem 1923
UNII 5UTX5635HP YesY
Properties
C9H7NO
Molar mass 145.16 g/mol
Appearance White crystalline needles
Density 1.034 g/cm3
Melting point 76 °C (169 °F; 349 K)
Boiling point 276 °C (529 °F; 549 K)
Pharmacology
ATC code G01AC30
A01AB07 D08AH03 R02AA14
Hazards
Main hazards flammable
Safety data sheet External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 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]

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, salen and salicylaldehyde isonicotinoylhydrazone (SIH). 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 in 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.[13]

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.

8-Hydroxyquinoline-functionalized hydrogels devices can be utilized to build photonic nanosensors to quantify the concentrations of lead and copper. The principle of operation of these sensors is based on the chemical modulation of a hydrogel film volume that incorporates a Bragg grating.[14] As the hydrogel swells or shrinks upon chemical stimulation, the Bragg grating changes color and diffracts light at different wavelengths. The diffracted light can be correlated with the concentration of a target analyte.

References

  1. ↑ Nanjing Odyssey Chemicals
  2. ↑ "8-Hydroxyquinoline Safety Data". Oxford University.
  3. ↑ "8-Hydroxyquinoline". PAN Pesticides Database.
  4. ↑ Collin, G.; Höke, H. (2005), "Quinoline and Isoquinoline", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a22_465
  5. ↑ 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.
  6. ↑ 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.
  7. ↑ Phillips, J. P. (1956). "The Reactions of 8-Quinolinol". Chemical Reviews 56 (2): 271–297. doi:10.1021/cr50008a003.
  8. ↑ "8-Hydroxyquinoline". Medical Dictionary Online.
  9. ↑ "8-Hydroxyquinoline". Sigma-Aldrich. Retrieved 2012-05-23.
  10. ↑ 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.
  11. ↑ 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. PMID 16841973.
  12. ↑ 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. PMID 16619313.
  13. ↑ Vivanco, J.M.; Bais, H.P.; Stermitz, F.R.; Thelen, G.C.; Callaway, R.M. (2004). "Biogeographical variation in community response to root allelochemistry: novel weapons and exotic invasion". Ecology Letters 7 (4): 285–292. doi:10.1111/j.1461-0248.2004.00576.x.
  14. ↑ Yetisen AK; Montelongo Y; Qasim MM; Butt H; Wilkinson TD; MJ Monteiro; Yun SH (2015). "Photonic Nanosensor for Colorimetric Detection of Metal Ions.". Anal. Chem. 87: 5101–5108. doi:10.1021/ac504274q.
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