8-Hydroxyquinoline

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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 3D model Interactive image
Interactive 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
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
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. 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 (OLEDs). 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.[citation needed]

Related compounds

Related ligands include the Schiff bases derived from salicylaldehyde, such as salicylaldoxime, salen, and salicylaldehyde isonicotinoylhydrazone (SIH). 8-Mercaptoquinoline is the thiol analogue of 8-hydroxyquinoline.

References

  1. Nanjing Odyssey Chemicals
  2. "8-Hydroxyquinoline Safety Data". Oxford University.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>[dead link]
  3. "8-Hydroxyquinoline". PAN Pesticides Database.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
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  8. "8-Hydroxyquinoline". Medical Dictionary Online.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
  9. "8-Hydroxyquinoline". Sigma-Aldrich. Retrieved 2012-05-23.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
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