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8-Hydroxyquinoline



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 148-24-3
PubChem 1923
SMILES OC1=C(N=CC=C2)C2=CC=C1
Properties
Molecular formula C9H7NO
Molar mass 145.16
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
Main hazards flammable
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

8-Hydroxyquinoline is an organic compound with the formula C9H6NOH. 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]

Additional recommended knowledge

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.

Applications

The complexes as well as the heterocycle itself exhibit antiseptic, disinfectant, and pesticide properties.[5][6] Its solution in alcohol are used as liquid bandages. It once was of interest as an anti-cancer drug.[7]

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.

Safety

See MSDS.[2]

References

  1. ^ Nanjing Odyssey Chemicals
  2. ^ a b Oxford University 8-hydroxyquinoline Safety Data
  3. ^ Pesticide Database
  4. ^ Gerd Collin, Hartmut Höke "Quinoline and Isoquinoline" Ullmann's Encyclopedia of Chemical Technology; 2005 Wiley-VCH, Weinheim.10.1002/14356007.a22 465
  5. ^ Phillips, J. P. “The Reactions Of 8-Quinolinol” Chemical Reviews 1956, volume 56, pp 271 - 297; DOI: 10.1021/cr50008a003
  6. ^ Medical Dictionary Online
  7. ^ Shen AY, Wu SN, Chiu CT (1999). "Synthesis and cytotoxicity evaluation of some 8-hydroxyquinoline derivatives". J. Pharm. Pharmacol. 51 (5): 543-8. PMID 10411213.



 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "8-Hydroxyquinoline". A list of authors is available in Wikipedia.
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