2388-32-1

Basic information

• Product Name: 2-Chloroquinoline-4-carbonyl chloride
• Synonyms: 2-CHLORO-QUINOLINE-4-CARBONYL CHLORIDE;2-CHLORO QUINOLINE-4-CHLOROFORMYL;2-CHLORO QUINOLINE-4-FORMYL CHLORIDE;2-ChloroQuinonline-4-Chloroformyl;2-Chloro-4-quinolinecarbonyl chloride
• CAS NO: 2388-32-1
• Molecular Formula: C₁₀H₅Cl₂NO
• Molecular Weight: 226.06
• EINECS: 219-220-5
• Mol File: 2388-32-1.mol
• Article Data: 20

Chemical Properties

• Melting Point: 89 °C(Solv: benzene (71-43-2))
• Boiling Point: 341.2 °C at 760 mmHg
• Flash Point: 160.2 °C
• Appearance: /
• Density: 1.457 g/cm³
• Vapor Pressure: 8.17E-05mmHg at 25°C
• Refractive Index: 1.66
• Storage Temp.: 2-8°C
• PKA: -2.82±0.50(Predicted)
• CAS DataBase Reference: 2-Chloroquinoline-4-carbonyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloroquinoline-4-carbonyl chloride(2388-32-1)
• EPA Substance Registry System: 2-Chloroquinoline-4-carbonyl chloride(2388-32-1)

Safety Data

• Hazardous Substances Data: 2388-32-1(Hazardous Substances Data)

Usage

General Description

2-Chloroquinoline-4-carbonyl chloride is a chemical compound that belongs to the class of organochlorine compounds. These are organic compounds containing a chlorine atom. In particular, this compound contains a quinoline, a nitrogen-containing aromatic compound with a two-ring structure. It is a relatively less researched chemical but is known to be used as a reagent in the synthesis of various complex molecules used in the pharmaceutical and chemical industries. Its properties, such as its physical state, boiling point, melting point, and specific gravity, may vary depending on its purity and other conditional factors. As with many chemicals, it should be handled with care to avoid any harm or reaction.

InChI:InChI=1/C10H5Cl2NO/c11-9-5-7(10(12)14)6-3-1-2-4-8(6)13-9/h1-5H

Upstream product

• 5467-57-2 2-chloroquinoline-4-carboxylic acid 
• 15733-89-8 2-quinolone-4-carboxylic acid 
• 91-56-5 indole-2,3-dione 
• 15733-89-8 2-hydroxyquinoline-4-carboxylic acid 

Downstream Products

• 135323-95-4 (2-chloro-quinolin-4-yl)-(morpholin-4-yl)-methanone 
• 861020-37-3 1-(2-chloro-quinoline-4-carbonyl)-4-phenyl-piperazine 
• 107779-36-2 2-(n-butyloxy)-4-(n-butyloxycarbonyl)-quinoline 
• 87864-14-0 2-chloro-quinoline-4-carboxylic acid-(2-diethylamino-ethylamide) 
• 135323-86-3 2-chloro-quinoline-4-carboxylic acid phenyl-amide 
• 135323-90-9 2-chloro-quinoline-4-carboxylic acid benzyl-amide 
• 39112-22-6 2-chloro-4-benzoylquinoline 
• 4295-16-3 2-chloroquinoline-4-carboxamide 
• 135323-89-6 2-Chloro-quinoline-4-carboxylic acid (4-methoxy-phenyl)-amide 
• 5467-61-8 ethyl ester of 2-chlorocinchoninic acid 
• 875585-54-9 N-benzyl-2-chloro-N-methylquinoline-4-carboxamide 
• 80947-25-7 2-chloroquinoline-4-amine 
• 50786-32-8 4-Amino-2-ethoxy-chinolin 
• 85-79-0 Dibucaine 

Relevant articles and documents

Identification of dibucaine derivatives as novel potent enterovirus 2C helicase inhibitors: In vitro, in vivo, and combination therapy study

Enterovirus A71 (EV-A71) is a human pathogen causing hand, foot and mouth disease (HFMD) which seriously threatened the safety and lives of infants and young children. However, there are no licensed direct antiviral agents to cure the HFMD. In this study, a series of quinoline formamide analogues as effective enterovirus inhibitors were developed, subsequent systematic structure-activity relationship (SAR) studies demonstrated that these quinoline formamide analogues exhibited good potency to treat EV-A71 infection. As described, the most efficient EV-A71 inhibitor 6i showed good anti-EV-A71 activity (EC50 = 1.238 μM) in RD cells. Furthermore, compound 6i could effectively prevent death of virus infected mice at dose of 6 mg/kg. When combined with emetine (0.1 mg/kg), this treatment could completely prevent the clinical symptoms and death of virus infected mice. Mechanism study indicated that compound 6i inhibited EV-A71 via targeting 2C helicase, thus impeding RNA remodeling and metabolism. Taken together, these data indicated that 6i is a promising EV-A71 inhibitor and worth extensive preclinical investigation as a lead compound.

Discovery of Novel Quinoline-Chalcone Derivatives as Potent Antitumor Agents with Microtubule Polymerization Inhibitory Activity

A series of novel quinoline-chalcone derivatives were designed, synthesized, and evaluated for their antiproliferative activity. Among them, compound 24d exhibited the most potent activity with IC50 values ranging from 0.009 to 0.016 μM in a panel of cancer cell lines. Compound 24d also displayed a good safety profile with an LD50 value of 665.62 mg/kg by intravenous injection, and its hydrochloride salt 24d-HCl significantly inhibited tumor growth in H22 xenograft models without observable toxic effects, which was more potent than that of CA-4. Mechanism studies demonstrated that 24d bound to the colchicine site of tubulin, arrested the cell cycle at the G2/M phase, induced apoptosis, depolarized mitochondria, and induced reactive oxidative stress generation in K562 cells. Moreover, 24d has potent in vitro antimetastasis and in vitro and in vivo antivascular activities. Collectively, our findings suggest that 24d deserves to be further investigated as a potent and safe antitumor agent for cancer therapy.

Method for preparing N-(2-(diethyl)aminoethyl)-2-chloro-4-quinolinecarboxamide

The invention discloses a method for preparing a dibucaine hydrochloride intermediate N-(2-(diethyl)aminoethyl)-2-chloro-4-quinolinecarboxamide by a one-pot method. The method comprises the followingsteps: using 2-hydroxy-4-carboxyquinoline and thionyl chloride to synthesize 2-chloroquinoline-4-formyl chloride under catalysis of DMF; concentrating a reaction liquid to dry; and directly reacting the product with N,N'-diethylethylenediamine under conditions of an acid binding agent to obtain N-(2-(diethyl)aminoethyl)-2-chloro-4-quinolinecarboxamide having a liquid phase purity of 99.9% or aboveand a yield of 93% or above. The method for preparing N-(2-(diethyl)aminoethyl)-2-chloro-4-quinolinecarboxamide has advantages of short production cycle, simple operation, low cost, high yield and high quality, and is conducive to industrial production.