| Identification | More | [Name]
8-Hydroxyquinoline | [CAS]
148-24-3 | [Synonyms]
8-HYDROXYQUINOLINE
8-HYDROXYQUINOLINE BASE
8-OXYQUINOLINE
8-QUINILINOL
8-QUINOLINOL
8-QUINOLINONE
BIOQUIN
HYDROXYQUINOLINE
OXINE
OXYQUINOLINE
QUINOPHENOL
TIMTEC-BB SBB009097
1-Azanaphthalene-8-ol
8-Chinolinol
8-Hydroxychinolin
8-hydroxy-chinolin
8-hydroxy-quinolin
8-OQ
8-Oxyquinolin
8-Quinol | [EINECS(EC#)]
205-711-1 | [Molecular Formula]
C9H7NO | [MDL Number]
MFCD00006807 | [Molecular Weight]
145.16 | [MOL File]
148-24-3.mol |
| Chemical Properties | Back Directory | [Appearance]
Cream-colored crystals | [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 at RT. | [solubility ]
0.56g/l | [form ]
Liquid | [pka]
5.017(at 20℃) | [color ]
White to pale yellow or light beige | [Water Solubility ]
INSOLUBLE | [Sensitive ]
Light Sensitive | [Detection Methods]
GC,NMR | [Merck ]
14,4843 | [BRN ]
114512 | [InChIKey]
MCJGNVYPOGVAJF-UHFFFAOYSA-N | [LogP]
1.85 at 25℃ | [CAS DataBase Reference]
148-24-3(CAS DataBase Reference) | [IARC]
3 (Vol. 13, Sup 7) 1987 | [NIST Chemistry Reference]
8-Quinolinol(148-24-3) | [Storage Precautions]
Light sensitive | [EPA Substance Registry System]
148-24-3(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed.
R68:Possible risk of irreversible effects.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [RIDADR ]
2811 | [WGK Germany ]
3
| [RTECS ]
VC4200000
| [Hazard Note ]
Harmful/Irritant | [TSCA ]
Yes | [HazardClass ]
9 | [PackingGroup ]
III | [HS Code ]
29334990 | [Safety Profile]
Poison by intraperitoneal and subcutaneous routes. Moderately toxic by ingestion. Questionable carcinogen with experimental carcinogenic, neoplastigenic, and tumorigenic data. Experimental reproductive effects. A central nervous system stimulant. Human mutation data reported. Combustible when exposed to heat or flame. When heated to decomposition it emits hghly toxic fumes of NOx. | [Hazardous Substances Data]
148-24-3(Hazardous Substances Data) | [Toxicity]
An 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). |
| Hazard Information | Back Directory | [Chemical Properties]
8-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). | [Originator]
Chinosol,Chinosolfabrik | [Uses]
8-Hydroxyquinoline(148-24-3) 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).
| [Application]
8-Hydroxyquinoline(148-24-3) 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).
| [Definition]
ChEBI: 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. | [Preparation]
8-Hydroxyquinoline(148-24-3) 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 name]
Aci-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 Function]
Antiseptic | [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 Description]
White to off-white or faintly yellow crystalline powder. Phenolic odor. | [Air & Water Reactions]
Insoluble in water. | [Reactivity Profile]
8-Hydroxyquinoline(148-24-3) darkens on exposure to light. 8-Hydroxyquinoline(148-24-3) readily forms stable metal chelates. 8-Hydroxyquinoline(148-24-3) is incompatible with strong oxidizers. 8-Hydroxyquinoline(148-24-3) is also incompatible with many metal ions. | [Hazard]
Toxic by ingestion. Questionable carcinogen. | [Biochem/physiol Actions]
8-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 Use]
8-Hydroxyquinoline (8HQ,148-24-3) 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.
| [Purification Methods]
Crystallise 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.] |
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