102878-20-6

Basic information

• Product Name: 2,4-dichloro-8-methylquinoline
• Synonyms: 2,4-dichloro-8-methylquinoline
• CAS NO: 102878-20-6
• Molecular Formula: C₁₀H₇Cl₂N
• Molecular Weight: 212.07528
• Mol File: 102878-20-6.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,4-dichloro-8-methylquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-dichloro-8-methylquinoline(102878-20-6)
• EPA Substance Registry System: 2,4-dichloro-8-methylquinoline(102878-20-6)

Safety Data

• Hazardous Substances Data: 102878-20-6(Hazardous Substances Data)

Usage

General Description

2,4-dichloro-8-methylquinoline is a chemical compound with the molecular formula C10H7Cl2N. It is a yellowish solid that is used as a building block in the synthesis of pharmaceuticals and agrochemicals. 2,4-dichloro-8-methylquinoline is primarily used in the development of antimalarial drugs and in the production of herbicides and insecticides. It is a potent inhibitor of the enzyme lactate dehydrogenase, which is essential for the growth and survival of the malaria parasite. Additionally, 2,4-dichloro-8-methylquinoline has shown potential as an antimicrobial agent and is being studied for its potential application in treating drug-resistant bacterial infections. Due to its biological activity and versatile chemical structure, this compound is of interest in the fields of medicinal chemistry and drug discovery.

Upstream product

• 141-82-2 malonic acid 
• 95-53-4 o-toluidine 
• 1677-42-5 8-methylquinoline-2,4-diol 
• 1677-42-5 4-hydroxy-8-methyl-1,2-dihydroquinolin-2-one 

Downstream Products

• 113226-20-3 4-chloro-8-methylquinoline-2(1H)-one 
• 1228173-79-2 2-[(2-benzoyl-4-chlorophenyl)amino]-4-chloro-8-methylquinoline 
• 1392408-90-0 2,4,5-tris(dimethylamino)-8-methylquinolinium monopicrate 
• 1386328-62-6 ethyl 4-(3-(2-chloro-8-methylquinolin-4-yloxy)phenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 
• 1424371-18-5 dimethyl 4-(4-(2-chloro-8-methylquinolin-4-yloxy)phenyl)-2,6-dimethyl-1,4-dihydro pyridine-3,5-dicarboxylate 
• 1424371-08-3 diethyl 4-(4-(2-chloro-8-methylquinolin-4-yloxy)phenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate 
• 360078-59-7 8-methyl-4-(triphenylphosphoranylideneamino)quinoline-2(1H)-thione 
• 360078-50-8 8-methyl-4-(triphenylphosphoranylideneamino)quinolin-2(1H)-one 

Relevant articles and documents

Synthesis, characterization, pharmacological, molecular modeling and antimicrobial activity evaluation of novel isomer quinoline derivatives

The structural and spectroscopic characteristics of the synthesized structurally novel compound 4-chloro-6-methylquinoline-2(1H)-one (4C6MQ) and its isomer 4-chloro-8-methylquinoline-2(1H)-one (4C8MQ) have been examined by means of experimental and computational quantum chemical methods like density functional theory (DFT). The crystal structure of the 4C6MQ compound has been brought to light by single-crystal x-ray diffraction (SCXRD) method which consists of two independent molecules (A and B) in the asymmetric unit with similar conformations. Both the isomer compounds are characterized spectroscopically by FTIR, FT-Raman, UV-Vis, and NMR spectrum and compared with DFT results. The geometries of the isomer compounds have been optimized by using DFT/B3LYP method with the 6-311G++(d,p) basis sets. From the optimized geometry of the compounds, geometric parameters (bond lengths, bond angles, and torsion angles); vibrational analysis; chemical shifts; and electronic absorption of the isomer compounds have been computed and compared with the experimental result. The detailed assignments of vibrational wave numbers have been prepared based on potential energy distribution (PED) which was carried out in the VEDA4 program. In addition, natural bonding orbital analysis, frontier molecular orbital, and molecular electrostatic potential have been explained theoretically. The in silico (absorption, distribution, metabolism, excretion and toxicity) studies were analyzed to identify the potential drug likeliness of the isomer compounds. The implications of the inhibitory activity of isomer compounds against DNA gyrase and lanosterol 14 α-demethylase enzyme by molecular docking are discussed. Further, the isomer compounds were screened for their antibacterial and antifungal activities.

Regioselective synthesis of novel 2-chloroquinoline derivatives of 1,4-dihydropyridines

Highly regioselective reaction of some substituted 2,4-dichloroquinolines with symmetrical 1,4-dihydropyridines, leading to novel quinoline derivatives of DHPs, has been achieved in the presence of powdered K2CO 3, as a mild and efficient base, at moderate temperature. All the synthesized compounds were characterized by use of IR, NMR, and mass spectral data.

Ultrasound-promoted synthesis, biological evaluation and molecular docking of novel 7-(2-chloroquinolin-4-yloxy)-4-methyl-2H-chromen-2-one derivatives

A series of quinoline-based coumarin derivatives have been synthesized by one pot dehydrochlorination of 2,4-dichloroquinolines (1a-g); 7-hydroxy-4-methyl-2H-chromen-2-one (2) under ultrasonic irradiation method with high regio selectivity. All the synthesized compounds were characterized through spectral data and screened against representative antibacterial and antioxidant activities. Some of the compounds are found to be equipotent or more potent than that of standard drugs. Molecular docking studies show that the binding energy value of the compounds is very less than that of standard chloroquine and amodiaquine drugs.