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8-Hydroxyquinoline

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8-Hydroxyquinoline Basic information
8-Hydroxyquinoline Chemical Properties
  • Melting point:70-73 °C(lit.)
  • Boiling point:267 °C752 mm Hg(lit.)
  • Density 1.0340
  • refractive index 1.4500 (estimate)
  • Flash point:267°C
  • storage temp. Store at RT.
  • solubility 0.56g/l
  • pka5.017(at 20℃)
  • form Liquid
  • color White to pale yellow or light beige
  • Water Solubility INSOLUBLE
  • Sensitive Light Sensitive
  • Merck 14,4843
  • BRN 114512
  • InChIKeyMCJGNVYPOGVAJF-UHFFFAOYSA-N
  • CAS DataBase Reference148-24-3(CAS DataBase Reference)
  • NIST Chemistry Reference8-Quinolinol(148-24-3)
  • EPA Substance Registry System8-Quinolinol (148-24-3)
Safety Information
MSDS
8-Hydroxyquinoline Usage And Synthesis
  • Chemical PropertiesCream-colored crystals
  • Usesantiinfectant, complexing agent
  • DefinitionChEBI: 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.
  • 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.
  • 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.
  • Fire HazardFlash point data for 8-Hydroxyquinoline are not available; however, 8-Hydroxyquinoline is probably combustible.
  • Clinical UseOxine, quinophenol, or oxyquinoline is the parent compoundfrom which the antiprotozoal oxyquinolines havebeen derived. The antibacterial and antifungal properties of oxine and its derivatives, which are believed to result fromthe ability to chelate metal ions, are well known. Aqueoussolutions of acid salts of oxine, particularly the sulfate(Chinosol, Quinosol), in concentrations of 1:3,000 to1:1,000, have been used as topical antiseptics. The substitutionof an iodine atom at the 7-position of 8-hydroxyquinolinesyields compounds with broad-spectrum amebicidalproperties.
  • Safety ProfilePoison 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.
  • 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.]
8-Hydroxyquinoline Preparation Products And Raw materials
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