171850-30-9

Basic information

• Product Name: 5,7-DICHLORO-4-HYDROXYQUINOLINE-3-CARBOXYLIC ACID
• Synonyms: 5,7-DICHLORO-4-HYDROXYQUINOLINE-3-CARBOXYLIC ACID;BUTTPARK 81\09-32;5,7-Dichloro-4-hydroxy-1-azanaphthalene-3-carboxylic acid, 3-Carboxy-5,7-dichloro-4-hydroxyquinoline;5,7-Dichloro-4-hydroxyquinoline-3-carboxylicacid97%
• CAS NO: 171850-30-9
• Molecular Formula: C10H5Cl2NO3
• Molecular Weight: 258.06
• EINECS: 431-250-2
• Mol File: 171850-30-9.mol

Chemical Properties

• Boiling Point: 428.3°Cat760mmHg
• Flash Point: 212.8°C
• Appearance: /
• Density: 1.651g/cm³
• Vapor Pressure: 4.26E-08mmHg at 25°C
• Refractive Index: 1.656
• PKA: 0.43±0.30(Predicted)
• CAS DataBase Reference: 5,7-DICHLORO-4-HYDROXYQUINOLINE-3-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 5,7-DICHLORO-4-HYDROXYQUINOLINE-3-CARBOXYLIC ACID(171850-30-9)
• EPA Substance Registry System: 5,7-DICHLORO-4-HYDROXYQUINOLINE-3-CARBOXYLIC ACID(171850-30-9)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 171850-30-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5,7-DICHLORO-4-HYDROXYQUINOLINE-3-CARBOXYLIC ACID is used as an antimicrobial agent for treating various bacterial infections, particularly urinary tract infections and respiratory infections. It works by inhibiting bacterial DNA synthesis and preventing pathogen replication, providing effective treatment for these conditions.
Used in Antimicrobial Research:
5,7-DICHLORO-4-HYDROXYQUINOLINE-3-CARBOXYLIC ACID is used as a research compound for studying its antimicrobial properties and potential applications in developing new antibiotics. Its unique mechanism of action and potential anti-inflammatory and antioxidant properties make it a valuable subject for research in the field of antimicrobial drug development.
Used in Drug Development:
5,7-DICHLORO-4-HYDROXYQUINOLINE-3-CARBOXYLIC ACID is used as a starting material or intermediate in the synthesis of new quinolone antibiotics. Its structure and properties can be modified to create novel compounds with improved antimicrobial activity, selectivity, and reduced side effects.
Used in Veterinary Medicine:
5,7-DICHLORO-4-HYDROXYQUINOLINE-3-CARBOXYLIC ACID is used as an antimicrobial agent in veterinary medicine for treating bacterial infections in animals. Its broad-spectrum activity and potential to combat antibiotic-resistant bacteria make it a valuable tool in veterinary practice.
Used in Cosmetics and Personal Care Products:
5,7-DICHLORO-4-HYDROXYQUINOLINE-3-CARBOXYLIC ACID is used as a preservative in cosmetics and personal care products to prevent microbial contamination and extend product shelf life. Its antimicrobial properties help maintain product safety and efficacy, ensuring consumer health and satisfaction.

InChI:InChI=1/C10H5Cl2NO3/c11-4-1-6(12)8-7(2-4)13-3-5(9(8)14)10(15)16/h1-3H,(H,13,14)(H,15,16)

Upstream product

• 93514-82-0 ethyl 4-hydroxy-5,7-dichloroquinoline-3-carboxylate 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 
• 626-43-7 3,5-Dichloroaniline 

Downstream Products

• 171850-29-6 4-hydroxy-5,7-dichloroquinoline 

Relevant articles and documents

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.

Method for preparing 4-hydroquinolines and/or tautomeric compounds

The invention concerns a method for preparing 4-hydroquinolines and/or tautomeric compounds. More particularly, the invention concerns 5,7-dichloro-4-quinolines and/or its tautomeric compounds. The method is characterized in that it consists in heating a 4-hydroquinolinecarboxylic acid, its derivatives or precursors, at a temperature not more than 200° C. in the presence of a base.

Intermediates for producing 5,7-dichloro-4-hydroxyquinoline

An industrially advantageous process for producing 5,7-dichloro-4-hydroxyquinoline (DCHQ) useful as an intermediate for agrohorticultural bactericides. The process comprises (i) hydrolyzing 3-cyano- or 3-ethoxycarbonyl-5,7-dichloro-4-hydroxyquinoline into 5,7-dichloro-3-carboxy-4-hydroxyquinoline (DCQA) in the presence of hydrochloric, sulfuric or phosphoric acid and (ii) decarboxylating the formed DCQA into DCHQ in the presence of sulfuric or phosphoric acid. In particular, this process comprises continuously conducting the hydrolysis of 5,7-dichloro-3-ethoxycarbonyl-4-hydroxyquinoline and the decarboxylation of the hydrolyzate in the presence of sulfuric acid having a specified concentration. The invention also relates to a process for producing DCQA by hydrolyzing 3-cyano- or 3-ethoxycarbonyl-5,7-dichloro-4-hydroxyquinoline in the presence of hydrochloric, sulfuric or phosphoric acid and a process for producing DCHQ by decarboxylating DCQA in the presence of sulfuric or phosphoric acid.