8-Hydroxyquinoline-N-oxide 1127-45-3

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8-Hydroxyquinoline-N-oxide Basic information Product Name: 8-Hydroxyquinoline-N-oxide Synonyms: 8-hydroxyquinoleine-N-oxide;NSC 21656;8-Hydroxyquinoline 1-Oxide;o-Hydroxyquinoline N-Oxide;8-Hydroxychinolin-N-oxid;1-oxido-8-quinolin-1-iumolate;1-Oxidoquinolin-1-ium-8-ol;1-Oxylato-8-hydroxyquinoline-1-ium CAS: 1127-45-3 MF: C9H7NO2 MW: 161.16 EINECS: 214-430-3 Product Categories: Quinoline derivatives;Quinolines, Isoquinolines & Quinoxalines;Quinolines;Aromatics Compounds;Aromatics;Heterocycles;Mutagenesis Research Chemicals;Quinolines, Isoquinolines & Quinoxalines;Morpholines/Thiomorpholines Mol File: 1127-45-3.mol 8-Hydroxyquinoline-N-oxide Chemical Properties Melting point  135-138 °C (lit.) Boiling point  267 °C(lit.) density  1.2480 (rough estimate) refractive index  1.5050 (estimate) Fp  139 °C storage temp.  Inert atmosphere,2-8°C solubility  Soluble in Acetone, Chloroform, Dichloromethane, Ethyl Acetate and Methanol pka 6.03±0.30(Predicted) form  Solid color  Yellow BRN  128737 InChI InChI=1S/C9H7NO2/c11-8-5-1-3-7-4-2-6-10(12)9(7)8/h1-6,11H InChIKey FJKUOCCQEBLPNX-UHFFFAOYSA-N SMILES [N+]1([O-])=C2C(C=CC=C2O)=CC=C1 CAS DataBase Reference 1127-45-3(CAS DataBase Reference) Safety Information Hazard Codes  N,Xi Risk Statements  50/53-36/37/38 Safety Statements  60-61-24/25-22-36/37/39-27-26 RIDADR  UN 3077 9/PG 3 WGK Germany  3 RTECS  VC8238500 F  3-10 HS Code  29334900 8-Hydroxyquinoline-N-oxide Usage And Synthesis Description A quinoline derivative that displays mutagenic activity. It suppresses luminescence of an indicator bacterium that is named Photobacterium phosphoreum. This chemical forms two kinds of complexes with palladium (II) and Gold (III). One kind is an ion-associated compound containing hydrogen bond and hte other is the six membered metal chelates containing metal-oxygen bonds. Chemical Properties Yellow Crystalline Solid Uses A quinoline derivative; shows mutagenic activity. Definition ChEBI: 8-hydroxyquinoline N-oxide is a quinoline N-oxide carrying a hydroxy substituent at position 8. It is a monohydroxyquinoline and a quinoline N-oxide. It is functionally related to a quinolin-8-ol. It is a conjugate acid of an 8-hydroxyquinoline N-oxide(1-). General Description 8-Quinolinol N-oxide is a toxicant which can suppress luminescence of an indicator bacterium Photobacterium phosphoreum. It forms two types of complexes with gold(III) and palladium(II): type I are ion-associated compounds containing hydrogen bond and the other is the six-membered metal chelates containing metal-oxygen bonds. Synthesis 8-hydroxyquinoline-N-oxide was synthesized from 8-hydroxyquinoline. A stirred solution of 8-hydroxyquinoline (25.00 g, 172.2 mmol) in 550 ml of CHCl3 was cooled to 0° C., and 3 -chloroperoxybenzoic acid (40.00 g, 80% Tech. grade *0.231 mmol=0.185 mmol) was added slowly over 3 minutes. The solution was kept at 0° C. and stirred for 3 hours. During this period, the 3-chlorobenzoic acid byproduct precipitated. The 3-chlorobenzoic acid was removed by filtration and the orange filtrate was concentrated to dryness and the remaining solid was triturated with 2% NH40 H (2*200 ml). The solid was isolated on a frit and washed with H2O. References [1] Naunyn-Schmiedeberg's Archives of Pharmacology, 1999, vol. 359, # 3, p. 168 - 177 [2] ChemCatChem, 2015, vol. 7, # 23, p. 3903 - 3910 [3] Patent: US2003/97000, 2003, A1 [4] Patent: US6617336, 2003, B1 [5] Organic Letters, 2011, vol. 13, # 14, p. 3556 - 3559 8-Hydroxyquinoline-N-oxide Preparation Products And Raw materials Raw materials perphthalic acid-->Hydrogen peroxide-->8-Hydroxyquinoline-->Manganese dioxide-->Dichloromethane-->Peroxyacetic acid-->Perbenzoic acid-->2-Aminophenol Preparation Products 2-chloroquinolin-8-ol-->8-Quinolinol, 2-(2-phenylethenyl)-



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