529-37-3

Basic information

• Product Name: 4-HYDROXYQUINOLINE
• Synonyms: QUINOLIN-4(1H)-ONE;QUINOLIN-4-OL;AKOS 222-32;4-HYDROXY-1-AZANAPHTHALENE;4(1H)-QUINOLINONE;KYNURINE;HYDROXYQUINOLINE,4-;HYDROXYQUINOLINE,4-(RG)
• CAS NO: 529-37-3
• Molecular Formula: C₉H₇NO
• Molecular Weight: 145.16
• EINECS: 210-268-2
• Mol File: 529-37-3.mol
• Article Data: 6

Chemical Properties

• Melting Point: 200-202 °C(lit.)
• Boiling Point: 261.5 °C at 760 mmHg
• Flash Point: 122.3 °C
• Appearance: /
• Density: 1.188 g/cm³
• Storage Temp.: 2-8°C
• PKA: 2.25±0.30(Predicted)
• CAS DataBase Reference: 4-HYDROXYQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-HYDROXYQUINOLINE(529-37-3)
• EPA Substance Registry System: 4-HYDROXYQUINOLINE(529-37-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: VC4070000
• Hazardous Substances Data: 529-37-3(Hazardous Substances Data)

Usage

Uses

Quinolin-4(1H)-one can be used to synthesize anti-cancer activity to overcome multidrug resistance in humans.

Upstream product

• 91-22-5 quinoline 
• 52980-28-6 ethyl 4-oxo-1,4-dihydroquinoline-3-carboxylate 
• 25063-47-2 2,2-dimethyl-5-(((2-nitrophenyl)amino)methylene)-1,3-dioxane-4,6-dione 
• 64-17-5 ethanol 
• 5257-06-7 N-(2-acetylphenyl)formamide 
• 7732-18-5 water 
• 89816-28-4 3-(N-benzylanilino)-acrylaldehyde 
• 34900-01-1 3-(N-methyl-N-phenylamino)acrolein 
• 81336-57-4 4-(benzoyloxy)quinoline 

Downstream Products

• 313535-86-3 3-benzylquinolin-4(1H)-one 
• 40695-01-0 1-phenyl-1,4-dihydroquinolin-4-one 
• 1616976-41-0 N-methyl-N-phenyl-2-(quinolin-4-yloxy)propanamide 

Relevant articles and documents

Unsymmetrical bisquinolines with high potency against P. falciparum Malaria

Quinoline-based scaffolds have been the mainstay of antimalarial drugs, including many artemisinin combination therapies (ACTs), over the history ofmoderndrugdevelopment. Althoughmuch progress has beenmade in the search for novel antimalarial scaffolds, itmay be that quinolineswill remain useful, especially if very potent compounds fromthis class are discovered. We report here the results of a structure-activity relationship(SAR) study assessingpotentialunsymmetrical bisquinoline antiplasmodial drug candidates using in vitro activity against intact parasites in cell culture. Many unsymmetrical bisquinolineswere found to be highly potent against both chloroquine-sensitive and chloroquine-resistant Plasmodium falciparum parasites. Further work to develop such compounds could focus on minimizing toxicities in order to find suitable candidates for clinical evaluation.

Probing the TiO2 photocatalytic mechanisms in water purification by use of quinoline, photo-fenton generated OH. radicals and superoxide dismutase

In an attempt to improve our understanding of the basic mechanisms of the degradation of aromatic pollutants in water by TiO2 photocatalysis, quinoline (benzo[b]pyridine) was selected as a molecular probe, principally because of the difference in electron density over its two rings. This study was based on the identification and quantification of the primary products or principal secondary products of quinoline degradation either by TiO2 photocatalysis at pH 3 and 6 or by OH. radicals generated via the photo-Fenton reaction (Fe(II/III)-H2O2-UV) at pH 3. In this latter case, the three major products were those expected from the preferential electrophilic attack of OH. radicals on the electron-richer benzene moiety, viz., 5-, and 8-hydroxyquinolines and quinoline-5,8-dione derived from them. TiO2 photocatalysis did not yield this dione, and at the same percentages of degraded quinoline, the amounts of 5-hydroxyquinoline were lower by a factor of ca. 2 at pH 3 and ca. 10 at pH 6 (those of the 8-isomer were also decreased but no accurate measurements were obtained). In addition, at pH 6, we observed marked increases in the amounts of products corresponding to the oxidation of the pyridine moiety, viz., 4-quinolinone and especially 2-aminobenzaldehyde (the major product) and its N-formyl derivative. These results show that oxidative steps in TiO2 photocatalysis do not involve only OH. radicals. It was also observed that, at pH 6, superoxide dismutase (SOD), which catalyzes the elimination of O2.- species, decreased the TiO2 photocatalytic rate of quinoline disappearance, almost suppressed the formation of 2-aminobenzaldehyde, and lowered the amount of 4-quinolinone. The SOD and pH effects suggest a mechanism involving quinoline activation by hole transfer, followed by superoxide addition to the resulting radical cation. The nucleophilic character of superoxide implies addition to the pyridine moiety, i.e., with a regioselectivity opposite that of the OH. radical pathway.

Process for the preparation of 4-amino-chloroquinolines

4-Amino-chloroquinolines of the formula: STR1 in which R1 represents a hydrogen atom or an alkyl radical (1 to 5 carbon atoms), and R2 represents an alkyl radical (1 to 5 carbon atoms) optionally substituted by a dialkylamino group, or a phenyl radical optionally substituted by one or more carboxy and hydroxy radicals and alkyl radicals (1 to 4 carbon atoms) optionally substituted by a dialkylamino group, are prepared by the condensation of an amine of the formula: STR2 with a chloro-1,2,3,4-tetrahydroquinolin-4-one of the formula: STR3 with aromatization of the tetrahydroquinoline, the reaction being carried out in the presence of a ruthenium based catalyst on a support. The 4-amino-chloroquinoline products are useful as pharmaceuticals.