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 
• 16600-22-9 7-chloro-4-hydroxyquinoline-3-carboxylic acid,ethyl ester 
• 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 

Downstream Products

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

Relevant articles and documents

Synthesis method of 4,7-dichloroquinoline

The invention discloses a synthesis method of 4,7-dichloroquinoline. The synthesis method is characterized by comprising the following steps: synthesizing 7-chloro-4-hydroxylquinoline-3-carboxylic acid by using a one-pot method, and carrying out decarboxylation and chlorination on the 7-chloro-4-hydroxylquinoline-3-carboxylic acid to obtain 4,7-dichloroquinoline. The step of synthesizing the 7-chloro-4-hydroxylquinoline-3-carboxylic acid by the one-pot method comprises the following sub-steps: with m-chloroaniline, triethyl orthoformate or trimethyl orthoformate and diethyl malonate as raw materials, carrying out condensation under the catalysis of anhydrous ferric trichloride to obtain diethyl 2-[[(3-chlorophenyl)amino]methylene]malonate, directly adding a condensation reaction solution into an organic solvent, carrying out heating cyclization to obtain 7-chloro-4-hydroxylquinoline-3-carboxylic acid ethyl ester, and after the cyclization reaction is completed, adding sodium hydroxidefor hydrolysis to obtain 7-chloro-4-hydroxylquinoline-3-carboxylic acid. Although the whole process comprises five reactions, intermediate products are good enough in purity and can be directly synthesized into a target product without purification, so operation is easy and convenient and industrialization is facilitated; and raw materials are easily available, and pollution is small.

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.