8-Hydroxyquinoline

8-Hydroxyquinoline Chemical Properties
Melting point 70-73 °C(lit.)
Boiling point 267 °C752 mm Hg(lit.)
density 1.0340
vapor pressure 0.221Pa at 25℃
refractive index 1.4500 (estimate)
Fp 267°C
storage temp. Store below +30°C.
solubility 0.56g/l
form Liquid
pka5.017(at 20℃)
color White to pale yellow or light beige
Water Solubility INSOLUBLE
Sensitive Light Sensitive
Merck 14,4843
BRN 114512
InChIKeyMCJGNVYPOGVAJF-UHFFFAOYSA-N
LogP1.85 at 25℃
CAS DataBase Reference148-24-3(CAS DataBase Reference)
IARC3 (Vol. 13, Sup 7) 1987
NIST Chemistry Reference8-Quinolinol(148-24-3)
EPA Substance Registry System8-Quinolinol (148-24-3)
Safety Information
Hazard Codes Xn,Xi
Risk Statements 22-68-36/37/38
Safety Statements 45-36/37/39-26-36
RIDADR 2811
WGK Germany 3
RTECS VC4200000
Hazard Note Harmful/Irritant
TSCA Yes
HazardClass 9
PackingGroup III
HS Code 29334990
Hazardous Substances Data148-24-3(Hazardous Substances Data)
ToxicityAn LD50 value of 1,200mg/kg was reported for oral administration of 8-hydroxyquinoline to rats (straidsex unspecified; AAPCO, 1966);a value of 48 mg/kg was reported for intraperitoneal administration to mice (strain/sex unspecxed; Bernstein et al., 1963).
MSDS Information
ProviderLanguage
8-Quinolinol English
SigmaAldrich English
ACROS English
ALFA English
8-Hydroxyquinoline Usage And Synthesis
Chemical Properties8-Hydroxyquinoline is a white to cream-colored crystal or crystalline powder that is insoluble in water or ether and freely soluble in ethanol, acetone, chloroform, benzene, and aqueous mineral acids. It readily forms stable metal chelates, which are soluble or precipitable in organic solvents, depending on the pH of the solution (Hollingshead, 1954).
OriginatorChinosol,Chinosolfabrik
Uses8-Hydroxyquinoline has a wide variety of uses. Primarily because of their metal chelating properties, 8-hydroxyquinoline and its salts, halogenated derivatives, and metal complexes have been used as analytical reagents (Hollingshead, 1954) and as antimicrobial agents in medicine, fungicides, and insecticides (Harvey, 1975). It is also used as a preservative in cosmetics and tobacco, a chemical intermediate in dye synthesis (IARC, 1977), and a precipitating reagent for uranium and other radioactive metals in nuclear power plant liquid waste effluent. It is used in nuclear medicine with indium-111 (Davis et al., 1978).
Application8-Hydroxyquinoline may be used as a chelating ligand in the preparation of tris-(8-hydroxyquinoline)aluminum (Alq3), an organic electroluminescent compound used in organic light-emitting devices (OLEDs).
DefinitionChEBI: 8-Hydroxyquinoline is a monohydroxyquinoline that is quinoline substituted by a hydroxy group at position 8. Its fungicidal properties are used for the control of grey mould on vines and tomatoes. It has a role as an antibacterial agent, an iron chelator, an antiseptic drug and an antifungal agrochemical. It derives from a hydride of a quinoline.
Preparation8-Hydroxyquinoline is synthesized from o-aminophenol by cyclization reaction. Add glycerin into the acid-resistant reaction pot, slowly add concentrated sulfuric acid under stirring, and simultaneously add o-aminophenol and o-nitrophenol in sequence, and add 65% of the total oleum first. Heat up to 125°C, stop heating, naturally heat up to 140°C, and wait until the temperature returns to 136°C. The rest of the oleum was continued to be added, maintaining the temperature at 137°C. After adding acid, keep warm for 4 hours, cool to below 100°C, pump into an acid-resistant pot containing 10 times the amount of water (calculated by o-aminophenol), stir, heat to 75-80°C, use 30% sodium hydroxide The solution was neutralized to pH 7-7.2. The precipitate is released while hot, cooled into a block, and sublimed under reduced pressure to obtain the finished product of 8-hydroxyquinoline.
Brand nameAci-jel;Benzease;Chinosol;Cp-cap;Dermacid;Dermoplast;Fennosan h 30;Heriat;Hydroxybenoxopyridine;Medicone derma-hc;Oxykin;Oxyquinoline-rhp;Pedivol;Phenopyridine;Preconsol;Quinoderm;Quinoped;Quinophenol;Recta medicone-hc;Semori;Serohinol;Serorhinol;Superol;Trimo-san;Triva douch powder;Triva jel.
Therapeutic FunctionAntiseptic
World Health Organization (WHO)Halogenated hydroxyquinoline is structurally related to clioquinol. See WHO comment for clioquinol. (Reference: (WHODI) WHO Drug Information, 77.1, 9, 1977)
General DescriptionWhite to off-white or faintly yellow crystalline powder. Phenolic odor.
Air & Water ReactionsInsoluble in water.
Reactivity Profile8-Hydroxyquinoline darkens on exposure to light. 8-Hydroxyquinoline readily forms stable metal chelates. 8-Hydroxyquinoline is incompatible with strong oxidizers. 8-Hydroxyquinoline is also incompatible with many metal ions.
HazardToxic by ingestion. Questionable carcinogen.
Biochem/physiol Actions8-Hydroxyquinoline is a RNA synthesis inhibitor that acts as a fungicide against Trichophyton mentagrophytes, Myrothecium verrucaria, and Trichoderma viride. The antifungal mechanism of action is not clear but appears to be structurally related.
Clinical Use8-Hydroxyquinoline (8HQ) is an intermediate of halogenated quinoline anti-amebic drugs, including quiniodoform, clioquinoline, diiodoquinoline and the like. These drugs exert anti-amebic effects by inhibiting intestinal commensal bacteria, and are effective against amoebic dysentery, but have no effect on extra-intestinal amoebic parasites.8HQ is a small planar molecule with a lipophilic effect and a metal chelating ability. As a result, 8HQ and its derivatives hold medicinal properties such as antineurodegenerative, anticancer, antioxidant, antimicrobial, anti-inflammatory, and antidiabetic activities.
Safety Profile8-Hydroxyquinoline (8-HQ) may be a skin irritant in man. Hair depigmentation was seen in mice treated dermally. Dilute solutions were slightly irritating to the eyes of rabbits. In cases of human poisoning (by ingestion or by the administration of an enema containing 8-HQ or its sulphate), the kidney, liver and blood were the principal sites of toxic attack. Comprehensive studies involving repeated oral administration of 8-HQ to rodents failed to identify any particular sites for toxic attack and provided no convincing evidence of carcinogenicity. 8-HQ induced chromosomal damage in mammalian cells in culture (including human cells), but gave conflicting results in mice treated intraperitoneally. Both 8-HQ and its sulphate have induced mutagenicity in Ames bacterial tests and there was some evidence of mutagenic activity in mammalian cells treated in culture.
Purification MethodsCrystallise oxine from hot EtOH, acetone, pet ether (b 60-80o) or water. Crude oxine can be purified by precipitation of copper oxinate, followed by liberation of free oxine with H2S or by steam distillation after acidification with H2SO4. Store it in the dark. It forms complexes with many metals. [Manske et al. Can J Research 27F 359 1949, Phillips Chem Rev 56 271 1956, Beilstein 21 III/IV 1135, 21/3 V 252.]
ETHYL 8-FLUORO-4-HYDROXYQUINOLINE-3-CARBOXYLATE broquinaldol ETHYL 6,8-DIMETHYL-4-HYDROXYQUINOLINE-3-CARBOXYLATE 8-HYDROXYQUINOLINE, MG 1-CYANO-1,2-DIHYDRO-2-HYDROXYQUINOLINE 8-Hydroxyquinoline-5-sulfonic acid ETHYL 4-HYDROXY-8-METHOXYQUINALDATE 5-Amino-8-quinolinol dihydrochloride 6-Fluoro-2,4-dihydroxyquinoline 8-ACETOXYQUINOLINE SNAZOXS ETHYL 6-BROMO-4-HYDROXYQUINOLINE-3-CARBOXYLATE 7-Chloroquinolin-4-ol 8-ETHOXYQUINOLINE-5-SULFONIC ACID SODIUM SALT 8-HYDROXYQUINOLINE-N-OXIDE Methyl 4-Hydroxyquinoline-2-carboxylate 8-HYDROXYQUINOLINE-BETA-D-GLUCOPYRANOSIDE,8-HYDROXYQUINOLINE-BETA-D-GLUCOSE 8-HYDROXYQUINOLINE, VANADIUM Hydroxyquinoline

Email:[email protected] [email protected]
Copyright © 2024 Mywellwork.com All rights reserved.