20146-59-2

Basic information

• Product Name: 4-CHLORO-2-HYDROXYQUINOLINE
• Synonyms: 4-CHLORO-2-HYDROXYQUINOLINE;4-chloroquinolin-2(1H)-one(SALTDATA: FREE);4-Chloroquinolin-2(1H)-one;4-Chloro-1H-quinolin-2-one;4-Chloroquinolin-2(1H)
• CAS NO: 20146-59-2
• Molecular Formula: C₉H₆ClNO
• Molecular Weight: 179.60304
• Mol File: 20146-59-2.mol
• Article Data: 12

Chemical Properties

• Melting Point: 254 °C
• Boiling Point: 366.9 °C at 760 mmHg
• Flash Point: 175.7 °C
• Appearance: /
• Density: 1.38 g/cm³
• Vapor Pressure: 1.42E-05mmHg at 25°C
• Refractive Index: 1.641
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 10.33±0.70(Predicted)
• CAS DataBase Reference: 4-CHLORO-2-HYDROXYQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-2-HYDROXYQUINOLINE(20146-59-2)
• EPA Substance Registry System: 4-CHLORO-2-HYDROXYQUINOLINE(20146-59-2)

Safety Data

• Hazardous Substances Data: 20146-59-2(Hazardous Substances Data)

Usage

General Description

4-CHLORO-2-HYDROXYQUINOLINE is a chemical compound with the molecular formula C9H6ClNO. It is a derivative of quinoline and contains a chloro and a hydroxy group at the 4 and 2 positions, respectively. 4-CHLORO-2-HYDROXYQUINOLINE is a yellow crystalline solid with antimicrobial properties, making it useful in the pharmaceutical and healthcare industries. It is also used as a building block in the synthesis of various other organic compounds. Additionally, 4-CHLORO-2-HYDROXYQUINOLINE has potential applications in the field of agrochemicals and is used as an intermediate in the production of pesticides and fungicides. Overall, this compound has diverse uses across different industries and is a valuable chemical in organic synthesis and antimicrobial applications.

InChI:InChI=1/C9H6ClNO/c10-7-5-9(12)11-8-4-2-1-3-6(7)8/h1-5H,(H,11,12)

Upstream product

• 703-61-7 2,4-dichloroquinoline 
• 105-13-5 4-Methoxybenzyl alcohol 

Downstream Products

• 703-61-7 2,4-dichloroquinoline 
• 91300-75-3 4-(4-benzyl-1-piperazinyl)-2(1H)-quinolinone hydrochloride 

Relevant articles and documents

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Identification and molecular modeling of new quinolin-2-one thiosemicarbazide scaffold with antimicrobial urease inhibitory activity

Abstract: A new series of 6-substituted quinolin-2-one thiosemicarbazides 6a–j has been synthesized. The structure of the target compounds was proved by different spectroscopic and elemental analyses. All the designed final compounds were evaluated for their in vitro activity against the urease-producing R. mucilaginosa and Proteus mirabilis bacteria as fungal and bacterial pathogens, respectively. Moreover, all compounds were in vitro tested as potential urease inhibitors using the cup-plate diffusion method. Compounds 6a and 6b were the most active with (IC50 = 0.58 ± 0.15 and 0.43 ± 0.09?μM), respectively, in comparison with lead compound I (IC50 = 1.13 ± 0.00?μM). Also, the designed compounds were docked into urease proteins (ID: 3LA4 and ID: 4UBP) using Open Eye software to understand correctly about ligand–receptor interactions. The docking results revealed that the designed compounds can interact with the active site of the enzyme through multiple strong hydrogen bonds. Moreover, rapid overlay of chemical structures’ analysis was described to understand the 3D QSAR of synthesized compounds as urease inhibitors. The results emphasize the importance of polar thiosemicarbazide directly linked to 6-substituted quinolone moieties as promising antimicrobial urease inhibitors. Graphic abstract: [Figure not available: see fulltext.]

Arylidenes of Quinolin-2-one scaffold as Erlotinib analogues with activities against leukemia through inhibition of EGFR TK/ STAT-3 pathways

A new series of 6-substiuted-4-(2-(4-substituted-benzylidene)hydrazinyl)quinolin-2(1H)-one derivatives have been designed and synthesized. The structure of the synthesized compounds was proved by 1H NMR, 13C NMR, 2D NMR, mass and elemental analyses. The target compounds were evaluated for their in vitro cytotoxic activity against 60 cancer cell lines according to NCI protocol. Consequently, the most active compounds were further examined against the most sensitive leukemia RPMI-8226 and on healthy cell lines. 6-Chloro-derivative was the most active one; with IC50 = 15.72 ± 1.21 and 46.05 ± 2.36 μM against RPMI-8226 and normal cell lines, respectively. Also, it showed a remarkable inhibitory activity compared to gefitinib on the EGFR TK mutant, wild and on H-RAS in addition to STAT-3 with IC50 = 695.49 ± 21.8, 263.15 ± 15.13, 10.61 ± 0.27 and 1.753 ± 0.81 nM, respectively. Cell cycle analysis of RPMI-8226 cells treated with the 6-chloro-derivative showed cell cycle arrest at G2/M phase (supported by Caspases-3,8, BAX and Bcl-2 studies) with a significant pro-apoptotic activity as indicated by annexin V-FITC staining. Moreover, the docking studies ROCS analysis and Tanimoto scores supported the results. The study illustrated the effect of several factors on compounds activity.