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5,7-Dichloro-8-hydroxyquinaldine

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5,7-Dichloro-8-hydroxyquinaldine Basic information
5,7-Dichloro-8-hydroxyquinaldine Chemical Properties
  • Melting point:108-112 °C (dec.)(lit.)
  • Boiling point:350.7±37.0 °C(Predicted)
  • Density 1.3126 (rough estimate)
  • refractive index 1.5500 (estimate)
  • storage temp. Keep in dark place,Sealed in dry,Room Temperature
  • pka2.47±0.30(Predicted)
  • Water Solubility Insoluble
  • Merck 13,2209
  • BRN 156683
  • CAS DataBase Reference72-80-0(CAS DataBase Reference)
  • NIST Chemistry ReferenceChlorquinaldol(72-80-0)
Safety Information
MSDS
5,7-Dichloro-8-hydroxyquinaldine Usage And Synthesis
  • Chemical Propertiesyellowish to beige-brown powder
  • OriginatorSterosan ,Geigy ,US ,1954
  • UsesChlorquinaldol is a fungistat and antibacterial agent in topical pharmaceutical preparations (5,7-dichloro-2-methyl-8-quinolinol, Sterosan).
  • Usesantiinfectant, antifungal
  • DefinitionChEBI: A monohydroxyquinoline that is quinolin-8-ol which is substituted by a methyl group at position 2 and by chlorine at positions 5 and 7. An antifungal and antibacterial, it was formerly used for topical treatment of skin conditions and vaginal infections.
  • Manufacturing Process11.1 parts of 8-hydroxy-quinaldine are dissolved in 140 parts of formic acid. Chlorine is introduced into this solution under cooling, until the increase in weight corresponds to the required quantity of chlorine and a test of the chlorination mixtures gives no more dyestuff formation with diazo-benzene in an acetic acid solution
    When the chlorination is complete, the reaction mixture is poured into 1,000 parts of water and treated with a dilute sodium bisulfite solution, until no more reaction may be observed with starch potassium iodide paper. Thereby the 5,7-dichloro-8-hydroxy-quinaldine separates out in form of a weakly yellowish colored precipitate. The same is filtered off and thoroughly washed with water.After drying, 15 parts of 5,7-dichloro-8-hydroxy-quinaldine melting at 111°C to 112°C are obtained. When recrystallized from alcohol, the product is obtained in voluminous, slightly yellowish needles having the melting point of 111.5°C to 112°C.
  • Therapeutic FunctionAntibacterial
  • Purification MethodsCrystallise it from EtOH. [Beilstein 21/3 V 346.]
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