128676-94-8

Basic information

• Product Name: 2-CHLOROQUINOLIN-3-OL
• Synonyms: 2-CHLOROQUINOLIN-3-OL;2-Chloro-3-hydroxyquinoline;3-Quinolinol, 2-chloro-
• CAS NO: 128676-94-8
• Molecular Formula: C9H6ClNO
• Molecular Weight: 179.6
• Mol File: 128676-94-8.mol

Chemical Properties

• Melting Point: >210℃
• Boiling Point: 315.201 °C at 760 mmHg
• Flash Point: 144.428 °C
• Appearance: /
• Density: 1.412
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 6.58±0.40(Predicted)
• CAS DataBase Reference: 2-CHLOROQUINOLIN-3-OL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLOROQUINOLIN-3-OL(128676-94-8)
• EPA Substance Registry System: 2-CHLOROQUINOLIN-3-OL(128676-94-8)

Safety Data

• Hazardous Substances Data: 128676-94-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-CHLOROQUINOLIN-3-OL is used as an antimalarial agent for its potential to combat malaria, a disease caused by Plasmodium parasites. Its unique structure allows it to target and disrupt the life cycle of the parasite, offering a new avenue for treatment.
2-CHLOROQUINOLIN-3-OL is also used as an antibacterial agent for its ability to inhibit the growth of various bacteria, which can be crucial in treating bacterial infections and developing new antibiotics to combat drug-resistant strains.
Furthermore, 2-CHLOROQUINOLIN-3-OL is used as an antiviral agent for its potential to treat viral infections by interfering with viral replication and assembly processes, providing a new approach to managing viral diseases.
Used in Chemical Synthesis:
2-CHLOROQUINOLIN-3-OL is used as a building block in the synthesis of various organic compounds, leveraging its unique structure to create new molecules with specific properties for different applications.
Used in Material Development:
2-CHLOROQUINOLIN-3-OL is used in the development of new materials, such as in the creation of organic semiconductors or as a component in advanced composites, due to its chemical and physical characteristics that can enhance material properties.

Upstream product

• 862249-68-1 2-chloro-3-lithioquinoline 
• 612-62-4 2-Chloroquinoline 
• 128676-84-6 (2-chloroquinolin-3-yl)boronic acid 

Downstream Products

• 26386-86-7 3-hydroxyquinolin-2(1H)-one 
• 856900-25-9 2-chloro-3-methoxymethoxy-quinoline 
• 847547-91-5 2-chloro-3-hydroxyquinoline-4-carboxylic acid 
• 1243531-74-9 C₂₂H₂₃ClN₂O₂ 

Relevant articles and documents

Enantioselective, intermolecular [2+2] photocycloaddition reactions of 3-acetoxyquinolone: Total synthesis of (-)-pinolinone

The natural product (-)-pinolinone was synthesised via a concise route (six steps, 17% overall yield) from 3-acetoxyquinolone, employing an enantioselective intermolecular [2+2] photocycloaddition as the key step. The Royal Society of Chemistry 2014.

Dioxygenase-catalyzed cis-dihydroxylation of pyridine-ring systems

Toluene dioxygenase-catalyzed dihydroxylation, in the carbocyclic rings of quinoline, 2-chloroquinoline, 2-methoxyquinoline, and 3-bromoquinoline, was found to yield the corresponding enantiopure cis-5,6- and -7,8-dihydrodiol metabolites using whole cells

THERAPEUTIC COMPOUNDS

no abstract published

HCV NS3 PROTEASE INHIBITORS

The present invention relates to macrocyclic compounds of formula (I) that are useful as inhibitors of the hepatitis C virus (HCV) NS3 protease, their synthesis, and their use for treating or preventing HCV infections.

A new approach to 3-hydroxyquinoline-2-carboxylic acid

Quinoline-2-carboxylic acid derivatives cap the N-terminal of several natural cyclic peptides with antitumoral activity. A new and convenient route for the preparation of 3-hydroxyquinoline-2-carboxylic acid is discussed. The preparation of the title compound is accomplished by a four-step procedure from 3-hydroxyquinoline via MOM protection of the hydroxyl group, followed by a 1,2-addition of methyllithium to the quinoline ring with concomitant oxidation, and, finally, a two-step oxidation procedure for the transformation of the methyl group to the carboxylic acid along with removal of the MOM group. Furthermore, different attempts to its preparation led to other interesting quinolines, such as 2-chloro-3-hydroxyquinoline-4-carboxylic acid and a protected 3,3′-dihydroxy-2,2′-biquinoline.

Directed ortho-Lithiation of Chloroquinolines. Application to Synthesis of 2,3-Disubstituted Quinolines

2-, 3- and 4-Chloroguinolines were selectively lithiated at low temperature by lithium diisopropylamide at the more acidic C-3, C-4 and C-3 positions respectively.Reaction of 2-chloro-3-lithioquinoline with electrophiles led to various 2,3-disubstituted quinolines.The versatility of this functionalization methodology is enhanced by the C-2 halogen reactivity towards oxygen or nitrogen nucleophiles.So, a great variety of 2,3-disubstituted quinolines were synthesized, such as 2-chloro, 2-alkoxy, 2-aminoquinolines or 2-quinolones bearing an hydroxy, carbonyl (aldehyde, ketone or carboxylic acid), iodo, trimethylsilyl or boronic acid moiety at the C-3.Some of the resulting 2,3-disubstituted synthons were annelated to tetracyclic polyaromatics, which possess the xanthone or indole structure.This could be achieved via further functionalization of the quinoline ring either by SNAr2 or heteroaromatic cross-coupling reactions, after the first directed-lithiation step.