4295-08-3

Basic information

• Product Name: 2-CHLORO-4-ETHOXYQUINOLINE
• Synonyms: 2-CHLORO-4-ETHOXYQUINOLINE;AURORA KA-3911
• CAS NO: 4295-08-3
• Molecular Formula: C₁₁H₁₀ClNO
• Molecular Weight: 207.66
• Product Categories: Aromatics;Heterocycles;Intermediates;Aromatics, Heterocycles, Intermediates
• Mol File: 4295-08-3.mol

Chemical Properties

• Boiling Point: 293.1°C at 760 mmHg
• Flash Point: 131.1°C
• Appearance: /
• Density: 1.227g/cm³
• Vapor Pressure: 0.00308mmHg at 25°C
• Refractive Index: 1.606
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• Solubility: Chloroform, Ethyl Acetate
• CAS DataBase Reference: 2-CHLORO-4-ETHOXYQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-4-ETHOXYQUINOLINE(4295-08-3)
• EPA Substance Registry System: 2-CHLORO-4-ETHOXYQUINOLINE(4295-08-3)

Safety Data

• Hazardous Substances Data: 4295-08-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Chloro-4-ethoxyquinoline is used as a key intermediate in the synthesis of compounds with anticonvulsant activity. It plays a crucial role in the development of medications aimed at treating seizure disorders and epilepsy by modulating the neuronal activity and reducing the frequency of seizures.
Additionally, 2-Chloro-4-ethoxyquinoline is utilized in the preparation of compounds with potent antibacterial activity against gram-positive pathogens. This application is significant in the field of antibiotics, as it helps in the development of new drugs to combat resistant bacterial strains and improve treatment outcomes for various infections caused by gram-positive bacteria.

InChI:InChI=1/C11H10ClNO/c1-2-14-10-7-11(12)13-9-6-4-3-5-8(9)10/h3-7H,2H2,1H3

Upstream product

• 64-17-5 ethanol 
• 703-61-7 2,4-dichloroquinoline 
• 141-52-6 sodium ethanolate 

Downstream Products

• 437716-09-1 2-[3-(3,4-Dichlorobenzylamino)prop-1-ylamino]-1H-quinolin-4-one 
• 54971-01-6 5-Aethoxy-s-triazol<4,3-a>chinolin. 
• 771555-21-6 2-chloroquinolin-4-ol 

Relevant articles and documents

Regioselective preparation and NMR spectroscopy study of 2-chloro-4-ethoxy-quinoline for the synthesis of 2-((3-aminopropyl)amino)quinolin-4(1H)-one

Herein, we describe the C4-ethoxylation of 2,4-dichloroquinoline to prepare 2-chloro-4-ethoxy-quinoline (3), which is a prominent intermediate used for the synthesis of 2-substituted quinolones. To achieve this goal, we studied different conditions for the reaction between 2,4-dichloroquinoline and sodium ethoxide. We discovered that the use of 18-crown-6 ether as an additive and dimethylformamide as the reaction solvent allowed us to obtain the desired product 3 in very good yield and selectivity. In addition, a definitive distinction between the C2 and C4 ethoxylation products was achieved using 1H─15N heteronuclear multiple bond correlation. Compound 3 is an intermediate used for the synthesis of 2-((3-aminopropyl)amino)quinolin-4(1H)-one, which displays peculiar behavior during 1H nuclear magnetic resonance analysis, such as the broadening of the H8 singlet and unexpected deuteration at the C8-position. Effort has been dedicated to understand these findings.

Preparation, antibacterial evaluation and preliminary structure-activity relationship (SAR) study of benzothiazol- and benzoxazol-2-amine derivatives

In this study, a novel benzothiazol- and benzooxazol-2-amine scaffold with antibacterial activity was designed and synthesized. Preliminary structure-activity relationship analysis displayed that compound 8t with a 5,6-difluorosubstituted benzothiazole was found to be a potent inhibitor of Gram-positive pathogens, and exhibited some potential against drug-resistant bacteria and without cytotoxicity in therapeutic concentrations. In addition, molecular docking studies indicated that Staphylococcus aureus methionyl-tRNA synthetase might be the possible target of these compounds. Taken together, the present study provides an effective entry to the synthesis of a good lead for subsequent optimization and a new small molecule candidate drug for antibacterial therapeutics.