86-47-5

Basic information

• Product Name: 7-CHLORO-4-HYDROXY QUINOLINE-3-CARBOXYLIC ACID
• Synonyms: usafkf-16;7-Chloro-4-Hydroxy-3-Carboxyquineoline;7-Chloro-4-Hydroxylquinoline-3;7-Chloro-4-hydroxy-3-quinolinecarboxalic acid;7-CHLORO-4-HYDROX-3-QUINOLINECARBOXYLIC ACIDCHLOROQUINE PHOSPHATE;4-Hydroxy-7-chloroquinoline-3-carboxylic acid;7-chloro-4-keto-1H-quinoline-3-carboxylic acid;4-Hydroxy-7-chloro-3-quinolinecarboxylic acid
• CAS NO: 86-47-5
• Molecular Formula: C₁₀H₆ClNO₃
• Molecular Weight: 223.61
• EINECS: 201-673-5
• Product Categories: Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Quinolines;QuinolinesHeterocyclic Building Blocks
• Mol File: 86-47-5.mol
• Article Data: 6

Chemical Properties

• Melting Point: 250 °C (dec.)(lit.)
• Boiling Point: 395 °C at 760 mmHg
• Flash Point: 192.7 °C
• Appearance: /
• Density: 1.600
• Vapor Pressure: 6E-07mmHg at 25°C
• Refractive Index: 1.648
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 0.65±0.30(Predicted)
• CAS DataBase Reference: 7-CHLORO-4-HYDROXY QUINOLINE-3-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 7-CHLORO-4-HYDROXY QUINOLINE-3-CARBOXYLIC ACID(86-47-5)
• EPA Substance Registry System: 7-CHLORO-4-HYDROXY QUINOLINE-3-CARBOXYLIC ACID(86-47-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: VB1950000
• Hazardous Substances Data: 86-47-5(Hazardous Substances Data)

Usage

Chemical Properties

Colorless to pale yellow granules

InChI:InChI=1/C10H6ClNO3/c11-5-1-2-6-8(3-5)12-4-7(9(6)13)10(14)15/h1-4H,(H,12,13)(H,14,15)

Upstream product

• 2458-23-3 7-chloro-4-hydroxyquinoline-3-carbonitrile 
• 108-42-9 3-chloro-aniline 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 
• 3412-99-5 2-(3-chlorophenylamino)methylenemalonic acid diethyl ester 
• 16596-00-2 N,N'-bis-(3-chloro-phenyl)-formamidine 
• 105-53-3 diethyl malonate 
• 16600-22-9 7-chloro-4-hydroxyquinoline-3-carboxylic acid,ethyl ester 

Downstream Products

• 86-98-6 4,7-dichloroquinoline 
• 54-05-7 Chloroquine 
• 5407-57-8 N-(7-chloroquinolin-4-yl)ethylenediamine 
• 86-99-7 7-chloro-4-hydroxylquinoline 

Relevant articles and documents

Preparation method 4-7 -dichloroquinoline (by machine translation)

The method comprises the steps of: adding 4 chloroaniline and ethoxymethyl diethyl malonate as raw materials, carrying out decarboxylation reaction, carrying out decarboxylation through condensation, cyclization and hydrolysis, carrying out decarboxylation reaction, adding sulfuric acid to 7 - under 3 - pressure, 4 and washing to obtain solid 7 - hydroxyl 3 - chloroquinolines. 230 - 260 °C. The method comprises the following steps: carrying out decarboxylation reaction, adding sulfuric acid to reaction completely, layering, organic layer recovery and water layer reaction till 90 - 100 °C 6.0 - 6.5 kg reaction until reaction is complete 90 - 100 °C, layering, organic layer recovery and water layer reaction; and the steps and chlorination are carried out 150 -170 °C pH4 - 5 4 -7 . Reaction conditions are mild, yield is high, and quality is good. (by machine translation)

Dichloro-4-quinolinol-3-carboxylic acid: Synthesis and antioxidant abilities to scavenge radicals and to protect methyl linoleate and DNA

5,7-, 5,8-, 6,8-, 7,8-Dichloro-4-quinolinol-3-carboxylic acid (5,7-, 5,8-, 6,8-, 7,8-DCQA) together with 7-chloro-4-quinolinol-3-carboxylic acid (7-CQA) and 4-quinolinol-3-carboxylic acid (QA) were synthesized to investigate the antioxidant properties. 5,7-DCQA exhibited the highest ability to scavenge 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS+.), 2,2′-diphenyl-1-picrylhydrazyl (DPPH) and galvinoxyl radicals. 6,8-DCQA possessed the highest efficacy to protect methyl linoleate against 2,2′-azobis(2-amidinopropane)dihydrochloride (AAPH)-induced oxidation. 5,7-, 5,8-DCQA and QA were able to retard the β-carotene-bleaching in β-carotene-linoleic acid emulsion. In addition, 5,8- and 6,8-DCQA efficiently protected DNA against hydroxyl radical (.OH)-mediated oxidation, and 5,8-DCQA and 7-CQA were active to protect DNA against AAPH-induced oxidation. Furthermore, only 7-CQA can protect DNA against Cu2+/glutathione (GSH)-mediated oxidation. Dichloro-4-quinolinol-3-carboxylic acids were potent to be antiradical drugs, and were worthy to be researched pharmacologically.

Antimalarials: Synthesis of 4-aminoquinolines that circumvent drug resistance in malaria parasites

The strategies described here have permitted the synthesis of a series of 4-aminoquinoline antimalarials. Substantive improvements over previous syntheses include nucleophilic substitution with neat amine rather than in phenol, regioselective reductive alkylation to convert the terminal primary amine (12a-20a) on the diaminoalkane side chain to a diethylamino group, and purification by column chromatography with basic alumina. The 1H nmr spectra obtained after regioselective reductive alkylation with sodium borodeuteride (in comparison with sodium borohydride) demonstrated that this reductive alkylation proceeds via formation and subsequent reduction of the corresponding diamides in situ.