8-Hydroxyquinoline

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, oxine

Identifiers

CAS number 148-24-3

PubChem 1923

ChemSpider 1847^Y

UNII 5UTX5635HP^Y

KEGG D05321^Y

ChEBI CHEBI:48981^Y

ChEMBL CHEMBL310555^Y

Jmol-3D images Image 1
Image 2

SMILES

Oc1cccc2cccnc12
c1cc2cccnc2c(c1)O

InChI

InChI=1S/C9H7NO/c11-8-5-1-3-7-4-2-6-10-9(7)8/h1-6,11H^Y
Key: MCJGNVYPOGVAJF-UHFFFAOYSA-N^Y
InChI=1/C9H7NO/c11-8-5-1-3-7-4-2-6-10-9(7)8/h1-6,11H
Key: MCJGNVYPOGVAJF-UHFFFAOYAG

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

Y (verify) (what is: Y/N?)
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]

Contents

1 Synthesis

2 As a chelating agent

3 Applications

4 References

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] 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.

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

^ 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. (1956). "The Reactions of 8-Quinolinol". Chemical Reviews 56 (2): 271. 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

v · d · eAntiseptics and disinfectants (D08)

Acridine derivatives
Ethacridine lactate • 9-Aminoacridine • Euflavine

Biguanides and amidines
Dibrompropamidine • Chlorhexidine^# • Propamidine • Hexamidine • Polihexanide

Phenol and derivatives
Hexachlorophene • Policresulen • Phenol • Triclosan • Chloroxylenol^# • Biphenylol • Fenticlor

Nitrofuran derivatives
Nitrofurazone

Iodine products
Iodine/octylphenoxypolyglycolether • Povidone-iodine^# • Diiodohydroxypropane

Quinoline derivatives
Dequalinium • Chlorquinaldol • Oxyquinoline • Clioquinol

Quaternary ammonium compounds
Benzalkonium • Benzethonium chloride • Cetrimonium (bromide/chloride) • Cetylpyridinium • Cetrimide • Benzoxonium chloride • Didecyldimethylammonium chloride

Mercurial products
Mercuric amidochloride • Phenylmercuric borate • Mercuric chloride • Mercurochrome • Thiomersal • Mercuric iodide

Silver compounds
Silver nitrate

Alcohols
Propanol (propyl alcohol) • Isopropanol (isopropyl alcohol) • Ethanol (ethyl alcohol)^#

Other
Potassium permanganate • Sodium hypochlorite • Hydrogen peroxide • Eosin • Tosylchloramide

^#WHO-EM. ^‡Withdrawn from market. Clinical trials: ^†Phase III. ^§Never to phase III

M: INT, SF, LCT

anat/phys/devp

noco(i/b/d/q/u/r/p/m/k/v/f)/cong/tumr(n/e/d), sysi/epon

proc, drug (D2/3/4/5/8/11)

v · d · eGynecological anti-infectives and antiseptics (G01)

Antibiotics
polyene antimycotic (Nystatin, Natamycin, Amphotericin B) • Candicidin • Chloramphenicol • Hachimycin • Oxytetracycline • Carfecillin • Mepartricin • Clindamycin • Pentamycin

Arsenic compounds
Acetarsol

Quinoline derivatives
Diiodohydroxyquinoline • Clioquinol • Chlorquinaldol • Dequalinium • Broxyquinoline • Oxyquinoline

Organic acids
Lactic acid • Acetic acid • Ascorbic acid

Sulfonamides
Sulfatolamide

Imidazole derivatives
Metronidazole • Clotrimazole • Miconazole • Econazole • Ornidazole • Isoconazole • Tioconazole • Ketoconazole • Fenticonazole • Azanidazole • Propenidazole • Butoconazole • Omoconazole • Oxiconazole • Flutrimazole

Triazole derivatives
Terconazole

Other
Clodantoin • Inosine • Policresulen • Nifuratel • Furazolidone • Methylrosaniline • Povidone-iodine • Ciclopirox • Protiofate • Lactobacillus fermentum • Copper usnate

M: ♀ FRS

anat/phys/devp

noco/cong/npls, sysi/epon

proc/asst, drug (G1/G2B/G3CD)

v · d · eAntiparasitics – antiprotozoal agents – Chromalveolate antiparasitics (P01)

Alveo-
late

Apicom-
plexa

Conoidasida/
(Coccidiostats)

Cryptosporidiosis

thiazole (Nitazoxanide)

Isosporiasis

Trimethoprim/sulfamethoxazole^#

Toxoplasmosis

Pyrimethamine • Sulfadiazine

Aconoidasida

Malaria

Individual
agents

Hemozoin
inhibitors

Aminoquinolines

(4-): Amodiaquine^# • Chloroquine^# • Hydroxychloroquine
(8-): Primaquine^# • Pamaquine

4-methanolquinolines

Mefloquine^#• Quinine^# • Quinidine

Other

Lumefantrine (combined with artemether)
Halofantrine
Pyronaridine

Antifolates

DHFR inhibitors
(antifols)

2,4-Diaminopyrimidines (pyrimethamine)
biguanides (proguanil^# • chlorproguanil)

Sulfonamides

Sulfadoxine • sulfamethoxypyrazine

Coformulation

Fansidar^# (sulfadoxine/pyrimethamine)

Sesquiterpene
lactones

Artemether^# • Artesunate^#• Dihydroartemisinin •
Arteether/Artemotil • Artemisinin

Other

Atovaquone (as Malarone)
Tetracycline • Doxycycline^#
Clindamycin

Combi-
nations

Fixed-dose (coformulated) ACTs

artemether-lumefantrine^#
artesunate-amodiaquine (ASAQ)
artesunate-mefloquine (ASMQ)
dihydroartemisinin-piperaquine
artesunate-pyronaridine

Other combinations
(not co-formulated)

artesunate/SP • artesunate/mefloquine •
quinine/tetracycline • quinine/doxycycline • quinine/clindamycin

Babesiosis

Clindamycin

Cilio-
phora

Balantidiasis: Tetracycline

Hetero-
kont
Blastocystosis: Metronidazole

^#WHO-EM. ^‡Withdrawn from market. Clinical trials: ^†Phase III. ^§Never to phase III

M: PRO

ambz, excv, chrm (strc)

ambz, excv, chrm

ambz, excv, chrm

Categories:
Antiseptics
Quinolinols

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, oxine
Identifiers
CAS number	148-24-3
PubChem	1923
ChemSpider	1847^Y
UNII	5UTX5635HP^Y
KEGG	D05321^Y
ChEBI	CHEBI:48981^Y
ChEMBL	CHEMBL310555^Y
Jmol-3D images	Image 1 Image 2
SMILES Oc1cccc2cccnc12 c1cc2cccnc2c(c1)O
InChI InChI=1S/C9H7NO/c11-8-5-1-3-7-4-2-6-10-9(7)8/h1-6,11H^Y Key: MCJGNVYPOGVAJF-UHFFFAOYSA-N^Y InChI=1/C9H7NO/c11-8-5-1-3-7-4-2-6-10-9(7)8/h1-6,11H Key: MCJGNVYPOGVAJF-UHFFFAOYAG
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
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Игры ⚽ Поможем сделать НИР

Look at other dictionaries:

hydroxyquinoline — noun Any of several isomeric phenols derived from quinoline, but especially quinolin 8 ol which is used as a chelating agent … Wiktionary
hydroxyquinoline — hy·droxy·quinoline … English syllables
hydroxyquinoline — “+ noun : any of seven hydroxy derivatives of quinoline; especially : oxine … Useful english dictionary
2-hydroxyquinoline 5,6-dioxygenase — In enzymology, a 2 hydroxyquinoline 5,6 dioxygenase (EC number|1.14.12.16) is an enzyme that catalyzes the chemical reaction:quinolin 2 ol + NADH + H+ + O2 ightleftharpoons 2,5,6 trihydroxy 5,6 dihydroquinoline + NAD+The 4 substrates of this… … Wikipedia
2-hydroxyquinoline 8-monooxygenase — In enzymology, a 2 hydroxyquinoline 8 monooxygenase (EC number|1.14.13.61) is an enzyme that catalyzes the chemical reaction:quinolin 2 ol + NADH + H+ + O2 ightleftharpoons quinolin 2,8 diol + NAD+ + H2OThe 4 substrates of this enzyme are… … Wikipedia
4-hydroxyquinoline 3-monooxygenase — In enzymology, a 4 hydroxyquinoline 3 monooxygenase (EC number|1.14.13.62) is an enzyme that catalyzes the chemical reaction:quinolin 4 ol + NADH + H+ + O2 ightleftharpoons quinolin 3,4 diol + NAD+ + H2OThe 4 substrates of this enzyme are… … Wikipedia
Калия Гидроксихинолин (Potassium Hydroxyquinoline) — соль калия, обладающая противогрибковыми, антибактериальными и дезодорирующими свойствами. Наносится на поверхность кожи в виде кремов или лосьонов (например, в сочетании с пероксидом бензоила в таких препаратах, как хинодерм (Quinodcrm) или… … Медицинские термины
8-hydroxyquinoline — A fungistat and chelating agent. SYN: quinolinol. * * * 8 hy·droxy·quin·o·line āt hī .dräk sē kwin əl .ēn n a derivative of quinoline that is used esp. in the form of its sulfate (C9H7NO)2·H2SO4 as a disinfectant, topical antiseptic,… … Medical dictionary
potassium hydroxyquinoline — a salt of potassium that has antifungal, antibacterial, and deodorant activities. It is applied to the skin in creams or lotions (e.g. in combination with benzoyl peroxide as Quinoderm or Quinoped) to treat skin infections and occasionally causes … Medical dictionary
Knorr quinoline synthesis — The Knorr quinoline synthesis is an intramolecular organic reaction converting a β ketoanilide to a 2 hydroxyquinoline using sulfuric acid. This reaction was first described by Ludwig Knorr (1859 1921) in 1886 [ Synthetische Versuche mit dem… … Wikipedia

Academic Dictionaries and Encyclopedias

8-Hydroxyquinoline

Contents

Synthesis

As a chelating agent

Applications

References

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Academic Dictionaries and Encyclopedias

Wikipedia

8-Hydroxyquinoline

Contents

Synthesis

As a chelating agent

Applications

References

Look at other dictionaries:

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