2585-04-8

Basic information

• Product Name: 6-Chloro-2-hydroxy-4-methylquinoline
• Synonyms: 6-Chloro-2-hydroxy-4-methylquinoline;6-Chloro-4-methylquinolin-2(1H)-one;6-CHLORO-4-METHYLQUINOLIN-2(1H)-OL;2-Hydroxy-4-Methyl-6-chloroquinoline;6-Chloro-1,2-dihydro-4-methyl-2-oxoquinoline;6-chloro-4-methyl-1H-quinolin-2-one;6-chloro-4-methyl-carbostyril;6-Chloro-4-methylquinolin-2(1H)
• CAS NO: 2585-04-8
• Molecular Formula: C10H8ClNO
• Molecular Weight: 193.6
• Mol File: 2585-04-8.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 379.3 °C at 760 mmHg
• Flash Point: 183.2 °C
• Appearance: /
• Density: 1.273 g/cm³
• Vapor Pressure: 5.92E-06mmHg at 25°C
• Refractive Index: 1.587
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 6-Chloro-2-hydroxy-4-methylquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Chloro-2-hydroxy-4-methylquinoline(2585-04-8)
• EPA Substance Registry System: 6-Chloro-2-hydroxy-4-methylquinoline(2585-04-8)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 2585-04-8(Hazardous Substances Data)

Usage

General Description

6-Chloro-2-hydroxy-4-methylquinoline is a chemical compound that belongs to the quinoline family. It is a pale yellow crystalline solid with the molecular formula C10H8ClNO. 6-Chloro-2-hydroxy-4-methylquinoline is widely used as an intermediate in the synthesis of pharmaceuticals, agrochemicals, and dyes. It has shown to have antifungal, antibacterial, and antiparasitic properties, making it a valuable building block in the development of new drugs and agrochemical products. Additionally, it has been studied for its potential in treating certain types of cancer and as an anti-inflammatory agent. Overall, 6-Chloro-2-hydroxy-4-methylquinoline is an important and versatile chemical with potential applications in various industries.

InChI:InChI=1/C10H8ClNO/c1-6-4-10(13)12-9-3-2-7(11)5-8(6)9/h2-5H,1H3,(H,12,13)

Upstream product

• 73339-34-1 3-oxo-glutaric acid bis-(4-chloro-anilide) 
• 101-92-8 4'-Chloroacetoacetanilide 
• 106-47-8 4-chloro-aniline 
• 124-38-9 carbon dioxide 
• 720681-64-1 4-chloro-2-(prop-1-en-2-yl)aniline 
• 4341-76-8 Ethyl 2-butynoate 
• 539-03-7 N-(4-chlorophenyl)acetamide 
• 20139-55-3 N-(2-methyl-4-chlorophenyl)-3-oxobutanamide 
• 103907-21-7 (6-chloro-2-hydroxy-[4]quinolyl)-acetic acid 
• 141-97-9 ethyl acetoacetate 

Downstream Products

• 90723-71-0 6-chloro-4-methyl-2-chloroquinoline 
• 32431-30-4 6-chloro-2-hydroxy-quinoline-4-carboxylic acid 
• 188062-67-1 6-Chloro-4-methyl-2-oxo-2H-quinoline-1-carboxylic acid [1-(2,4-dichloro-phenyl)-meth-(E)-ylidene]-hydrazide 
• 188062-61-5 1-(4-nitrobenzylidenehydrazido)-6-chloro-4-methylquinolin-2-one 
• 188062-63-7 6-Chloro-4-methyl-2-oxo-2H-quinoline-1-carboxylic acid [1-(2-nitro-phenyl)-meth-(E)-ylidene]-hydrazide 
• 188062-65-9 6-Chloro-4-methyl-2-oxo-2H-quinoline-1-carboxylic acid [1-(2-chloro-phenyl)-meth-(E)-ylidene]-hydrazide 

Relevant articles and documents

Ru-NHC-Catalyzed Asymmetric Hydrogenation of 2-Quinolones to Chiral 3,4-Dihydro-2-Quinolones

Direct enantioselective hydrogenation of unsaturated compounds to generate chiral three-dimensional motifs is one of the most straightforward and important approaches in synthetic chemistry. We realized the Ru(II)-NHC-catalyzed asymmetric hydrogenation of 2-quinolones under mild reaction conditions. Alkyl-, aryl- and halogen-substituted optically active dihydro-2-quinolones were obtained in high yields with moderate to excellent enantioselectivities. The reaction provides an efficient and atom-economic pathway to construct simple chiral 3,4-dihydro-2-quinolones. The desired products could be further reduced to tetrahydroquinolines and octahydroquinolones.

Free energy perturbation guided Synthesis with Biological Evaluation of Substituted Quinoline derivatives as small molecule L858R/T790M/C797S mutant EGFR inhibitors targeting resistance in Non-Small Cell Lung Cancer (NSCLC)

Two different schemes of novel substituted quinoline derivatives were designed and synthesized via simple reaction steps and conditions. A comparative molecular docking study was carried out on two different types of EGFR enzymes which include wild-type (PDB: 4I23) and T790M mutated (PDB: 2JIV) respectively. Compounds were also validated upon T790M/C797S mutated (PDB ID: 5D41) EGFR enzyme at the allosteric binding site. Free energy perturbations were carried out to determine the absolute binding free energy of a protein–ligand complex in the form of ΔGbinding, which in turn provided 4ab and 5ad as the most potential contenders through the structural enhancement in the determined initial scaffolds. Anticancer activity of the synthesized derivatives was examined against HCC827, H1975 (L858R/T790M), A549, and HT-29 cell lines by standard MTT assay. Compound 4ad (6-chloro-2-(isoindolin-2-yl)-4-methylquinoline) has shown excellent inhibitory activities against mutant EGFR kinase with IC50 value 0.91 μM. The potency of compounds 4ab, 4ad and 5ad was compared through an insilico ADMET study.

Discovery, synthesis and molecular substantiation of N-(benzo[d]thiazol-2-yl)-2-hydroxyquinoline-4-carboxamides as anticancer agents

The effort was taken to develop a series of benzothiazole and quinoline fused bioactive compounds obtained through a four-step synthetic route using a range of substituted acetoacetanilides. Achieved N-(benzo[d]thiazol-2-yl)-2-hydroxyquinoline-4-carboxamides (6a-l) were produced up to 96% of yield while the eco-friendly p-TSA used as a catalyst. Further, the anticancer activity of these compounds was determined using a range of cancer cell lines starting from MCF-7 (Breast cancer), HCT-116 (Colon cancer), PC-3 & LNCaP (Prostate) and SK-HEP-1 (Liver cancer). Present study compounds were also testified for antioxidant properties prior to anticancer studies since the Reactive Oxygen Species (ROS) being vital in cancer development. To determine the cell membrane stability effects of the compounds, human red blood cells (HRBC) based membrane protection assay was determined. In the results, compounds 6a-l were able to produce a dominated result values over PC3 cell lines (Prostate cancer) than the other cell lines used in this study. Since the connectivity of human germ cell alkaline phosphatase (hGC-ALP) in the development of prostate cancer is known, the most active compounds were evaluated for the hGC-ALP inhibition in order to ensure a mechanism of anticancer action of these compounds. The mode of interaction and binding affinity of these compounds was also investigated by a molecular docking study. In the results, 6d, 6i, 6k, and 6l were found with least IC50 values 0.075 μM and highest relative activity of 92%, 90%, and 96% respectively. The need for further animal model evaluation and pre-clinical studies recognized.