1127-45-3

Basic information

• Product Name: 8-Hydroxyquinoline-N-oxide
• Synonyms: 8-hydroxyquinoleine-N-oxide;1-Oxidoquinolin-1-ium-8-ol;1-Oxylato-8-hydroxyquinoline-1-ium;8-Hydroxyquinoline-N-oxide,99%;8-Hydroxyquinoline-N;Quinolin-8-ol N-oxide;8-Quinolinol N-oxide 98%;1-Oxy-quinolin-8-ol
• CAS NO: 1127-45-3
• Molecular Formula: C₉H₇NO₂
• Molecular Weight: 161.16
• EINECS: 212-562-6
• Product Categories: Quinolines, Isoquinolines & Quinoxalines;Morpholines/Thiomorpholines;Quinoline derivatives;Quinolines, Isoquinolines & Quinoxalines;Quinolines;Aromatics Compounds;Aromatics;Heterocycles;Mutagenesis Research Chemicals
• Mol File: 1127-45-3.mol
• Article Data: 53

Chemical Properties

• Melting Point: 71-73 °C(lit.)
• Boiling Point: 267 °C(lit.)
• Flash Point: 139 °C
• Appearance: Yellow crystalline solid
• Density: 1.2480 (rough estimate)
• Vapor Pressure: 2.12E-06mmHg at 25°C
• Refractive Index: 1.5050 (estimate)
• Storage Temp.: Refrigerator
• Solubility: Soluble in Acetone, Chloroform, Dichloromethane, Ethyl Acetate and Methanol
• PKA: 6.03±0.30(Predicted)
• BRN: 128737
• CAS DataBase Reference: 8-Hydroxyquinoline-N-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: 8-Hydroxyquinoline-N-oxide(1127-45-3)
• EPA Substance Registry System: 8-Hydroxyquinoline-N-oxide(1127-45-3)

Safety Data

• Hazard Codes: N,Xi
• 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
• Hazardous Substances Data: 1127-45-3(Hazardous Substances Data)

Usage

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.

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.

InChI:InChI=1/C9H7NO2/c11-8-5-1-3-7-4-2-6-10(12)9(7)8/h1-6,11H

Upstream product

• 148-24-3 8-quinolinol 
• 64741-01-1 m-chloroperoxybenzoic acid 
• 2311-91-3 monoperoxyphthalic acid 
• 93-59-4 Perbenzoic acid 
• 79-21-0 peracetic acid 

Downstream Products

• 15450-72-3 2-oxo-1,2-dihydroquinolin-8-yl acetate 
• 37543-75-2 (E)-2-(2-phenylethenyl)-8-hydroxyquinoline 
• 21168-33-2 5,7-dichloro-8-hydroxyquinoline 1-oxide 
• 63543-87-3 8-hydroxy-2-methylquinoline 1-oxide 
• 148-24-3 8-quinolinol 
• 6961-25-7 2-phenyl-8-hydroxy-quinoline 
• 100331-89-3 8-benzyloxy-5-(2-bromoacetyl)-1H-quinolin-2-one 
• 93609-84-8 5-acetyl-8-benzyloxy-1H-quinolin-2-one 
• 62978-73-8 5-acetyl-8-hydroxy-2(1H)-quinolinone 
• 1254098-87-7 4-[({5-[2-({[4-({[(2R)-2-hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl]amino}methyl)phenyl]methyl}carbamoyl)ethyl]-2-phenylphenyl}carbamoyl)oxy]-1,1-dimethylpiperidin-1-ium trifluoroacetate 
• 1254102-84-5 5-[(1R)-2-bromo-1-hydroxyethyl]-8-[(4-methoxyphenyl)methoxy]-1,2-dihydroquinolin-2-one 
• 1254102-83-4 5-(2-bromoacetyl)-8-[(4-methoxyphenyl)methoxy]-1,2-dihydroquinolin-2-one 
• 956235-09-9 5-acetyl-8-[(4-methoxyphenyl)methoxy]-1,2-dihydroquinolin-2-one 
• 70125-16-5 2-amino-8-quinolinol 

Relevant articles and documents

Blue and white light electroluminescence in a multilayer OLED using a new aluminium complex

Synthesis, structure, optical absorption, emission and electroluminescence properties of a new blue emitting Al complex, namely, bis-(2-amino-8- hydroxyquinolinato), acetylacetonato Al(III) are reported. Multilayer OLED using the Al complex showed blue emission at 465 nm, maximum brightness of ～ 425 cd/m2 and maximum current efficiency of 0.16 cd/A. Another multilayer OLED using the Al complex doped with phosphorescent Ir complex showed 'white' light emission, CIE coordinate (0.41, 0.35), maximum brightness of ～ 970 cd/m2 and maximum current efficiency of 0.53 cd/A. Indian Academy of Sciences.

SYNTHESIS OF LAVENDAMYCIN

A regiospecific and convergent synthesis of Lavendamycin (1) starting from 8-hydroxyquinoline and indole via Bischler-Napieralski cyclisation is described.

Oxo-rhenium(V) complexes with 8-hydroxyquinoline derivatives

Compounds of the types ReOCl2(L)(PPh3) and ReOCl(L)2 were prepared by reacting ReOCl3(PPh 3)2 with 8-hydroxyquinoline (HL) and its 2-methyl, 2-chloro, 5-chloro, 5-nitro, 5,7-dichloro, 5,7-dibromo, and 5,7-diiodo derivatives. With the bulky 2-phenyl-8-hydroxyquinoline, only ReOCl 2(L)(PPh3) could be isolated, whereas the still bulkier 2-tert-butyl derivative did not react. For ReOCl2(L)(PPh 3), the coordination of the quinoline oxygen trans to the Re=O bond and the cis-dichloro arrangement in the equatorial plane were established from crystallographic studies on the 2-chloro and the 5,7-dibromo complexes. From the combined data for these various derivatives, the 1H NMR signals could be fully assigned. With both series of compounds, a complex d-d absorption pattern is observed in the visible spectra, corresponding to the excitation of a d electron from the interaxial d orbital in the equatorial plane to the empty dxz and dyz orbitals, which are inequivalent in these low-symmetry systems. Deconvolution revealed the presence of two very weak low-energy components (～10 000 and ～12 000 cm-1), which are assigned to the two expected singlet-triplet transitions, whereas two stronger bands at higher energy (～14 000 and ～17 000 cm-1) originate from the two singlet-singlet transitions. These bands are not substantially displaced by substitution on the 8-hydroxyquinoline rings.

Palladium-catalyzed alkenylation of quinoline-N-oxides via C-H activation under external-oxidant-free conditions

(Chemical Equation Presented) The direct cross-coupling of quinoline-N-oxides with olefin derivatives has been realized using palladium acetate as the catalyst in the absence of external ligand and oxidant to give the corresponding 2-alkenylated quinolines and 1-alkenylated isoquinolines chemo- and regioselectively in 27-95% yield. The catalytic process is proposed to proceed via direct C-H bond activation of the quinoline-N-oxide with Pd(OAc)2 followed by Heck coupling with the olefin. The resultant N-oxide of the alkenylated quinoline can oxidize the reduced Pd(0) to regenerate the Pd(II) active species and simultaneously release the 2-alkenylated quinoline without using any external oxidants and reductants.

SYNTHESIS OF A NOVEL HEXADENTATE CHELATING AGENT BASED ON 8-HYDROXYQUINOLINE

A new hexadentate chelator was synthesized by the functionalization of 8-hydroxyquinoline to its 2-carboxy-N-hydroxysuccinimidyl ester and a subsequent condensation with tris(2-aminoethyl)amine to give tris-N-(2-aminoethyl-)amine.This molecule is a siderophore analog with a non-naturally occurring binding unit comprising a combination of both oxygen and nitrogen donor atoms.

Hydrazo coupling: The efficient transition-metal-free C-H functionalization of 8-hydroxyquinoline and phenol through base catalysis

Azodicarboxylate esters are common reagents in organic synthesis laboratories due to their utility in the Mitsunobu reaction. They can also be regarded as possible starting compounds for C-H functionalization, which up until now has been mainly achieved by transition-metal-catalyzed reactions. We have developed a novel reaction involving the quantitative coupling of 8-hydroxyquinoline or phenol with azodicarboxylate esters. The functionalization proceeds under mild base-catalyzed conditions selectively, and either the ortho-position of 8-hydroxyquinoline or para-position of the phenol/naphthol is involved in the reaction. This type of transformation can be considered as "hydrazo coupling" (by analogy with azo coupling). Herein, we discuss a plausible mechanism for this catalyzed substitution, backing up our findings with deuterium NMR experiments and by varying the starting compounds and bases. Using Boc-NN-Boc as a substrate, we have developed the convenient and efficient synthesis of (8-hydroxyquinolin-7-yl)hydrazines, as well as demonstrating a new stereoselective route for the synthesis of medicinally important 4-hydroxyphenylhydrazine for laboratory use, which almost doubles the yield of the common industrial process and reduces the number of synthetic steps. A new "one-pot" procedure for the synthesis of aromatic 8-hydroxyquinolin-7-yl hydrazones was applied.

Synthesis of 2-Alkenylquinoline by Reductive Olefination of Quinoline N-Oxide under Metal-Free Conditions

Synthesis of 2-alkenylquinoline by reductive olefination of quinoline N-oxide under metal-free conditions is disclosed. Practically, the reaction could be performed with quinoline as starting material via a one-pot, two-step process. A possible mechanism is proposed that involves a sequential 1,3-dipolar cycloaddition and acid-assisted ring opening followed by a dehydration process.

O-prenylated carbostyrils as a novel class of 15-lipoxygenase inhibitors: Synthesis, characterization, and inhibitory assessment

Catalyzed peroxidation of unsaturated lipid in animals and plants intimately is linked to the activity of 15-Lipoxygenase enzymes. Lipoxygenases (LOXs) are well known to play an important role in many acute and chronic syndromes such as inflammation, asthma, cancer, and allergy. In this study, a series of mono prenyloxycarbostyrils were synthesized and evaluated as potential inhibitors of soybean 15-Lipoxygenase (SLO) and their inhibitory potencies were compared to mono prenyloxycoumarins which had been reported in the previous works. The synthetic compounds inhibit lipoxygenase enzyme by competitive mechanism like the prenyloxy coumarins. The results showed that position and length of the prenyl moiety play the important role in lipoxygenase inhibitory activity. Among all of the synthetic compounds (coumarin and carbostyril derivatives), 5-farnesyloxycoumarin and 8-farnesyloxycarbostyril demonstrated the best inhibitory activity by IC50?values of 1.1?μM and 0.53?μM, respectively.

Method for preparing azaheterocycle-N-oxides

The invention relates to a method for preparing azaheterocycle-N-oxides. The method is concretely characterized in that pyridine, quinoline and isoquinoline compounds, which are used as raw materials,are oxidized under the action of a catalyst to obtain the corresponding N-oxides. The method for preparing azaheterocycle-N-oxides is a preparation method having the advantages of high yield, low cost, easiness in operation, and suitableness for industrialization.