57659-08-2

Basic information

• Product Name: 2-HYDROXYQUINOLINE-4-FORMYLCHLORIDE
• Synonyms: 2-HYDROXYQUINOLINE-4-FORMYLCHLORIDE;4-Quinolinecarbonyl chloride, 1,2-dihydro-2-oxo- (9CI)
• CAS NO: 57659-08-2
• Molecular Formula: C₁₀H₆ClNO₂
• Molecular Weight: 207.61
• Product Categories: ACIDHALIDE
• Mol File: 57659-08-2.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 427.9 °C at 760 mmHg
• Flash Point: 212.6 °C
• Appearance: /
• Density: 1.466 g/cm³
• Vapor Pressure: 6.31E-08mmHg at 25°C
• Refractive Index: 1.693
• CAS DataBase Reference: 2-HYDROXYQUINOLINE-4-FORMYLCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-HYDROXYQUINOLINE-4-FORMYLCHLORIDE(57659-08-2)
• EPA Substance Registry System: 2-HYDROXYQUINOLINE-4-FORMYLCHLORIDE(57659-08-2)

Safety Data

• Hazardous Substances Data: 57659-08-2(Hazardous Substances Data)

Usage

Description

2-Hydroxyquinoline-4-formylchloride, also known as 4-chloro-2-hydroxyquinoline-4-carboxaldehyde, is a chemical compound with the molecular formula C10H6ClNO2. It is a derivative of quinoline and is commonly used in the synthesis of pharmaceuticals and organic compounds. It is a light yellow crystalline solid, and its structure consists of a quinoline ring with a hydroxyl group at the 2-position and a formylchloride group at the 4-position. 2-Hydroxyquinoline-4-formylchloride is an important intermediate and building block in the preparation of various functionalized quinolines and quinoline-derived compounds, which have been found to exhibit a wide range of biological activities and applications in medicinal chemistry.

Uses

Used in Pharmaceutical Industry:
2-Hydroxyquinoline-4-formylchloride is used as an intermediate for the synthesis of various pharmaceuticals and organic compounds. Its unique structure allows for the development of functionalized quinolines and quinoline-derived compounds with a wide range of biological activities, making it a valuable building block in medicinal chemistry.
Used in Organic Chemistry:
2-Hydroxyquinoline-4-formylchloride is used as a reagent and building block in organic chemistry for the synthesis of various organic compounds. Its versatility and unique structure enable the creation of a diverse array of molecules with potential applications in various fields.
Used in Medicinal Chemistry:
2-Hydroxyquinoline-4-formylchloride is used as a key intermediate in the preparation of quinoline-based drugs and therapeutic agents. Its ability to form functionalized quinolines and quinoline-derived compounds with significant biological activities makes it an essential component in the development of new medications and treatments.

InChI:InChI=1/C10H6ClNO2/c11-10(14)7-5-9(13)12-8-4-2-1-3-6(7)8/h1-5H,(H,12,13)

Upstream product

• 91-56-5 indole-2,3-dione 
• 15733-89-8 2-hydroxyquinoline-4-carboxylic acid 
• 607-66-9 4-methylquinolin-2-ol 
• 102-01-2 N-phenylacetoacetamide 
• 15733-89-8 2-quinolone-4-carboxylic acid 

Downstream Products

• 325822-27-3 2-oxo-N-phenyl-1,2-dihydroquinoline-4-carboxamide 
• 325822-33-1 1,2-dihydro-2-oxoquinoline-4-carboxy-(4-methoxyphenyl)amide 

Relevant articles and documents

Discovery of SARS-CoV-2 main protease inhibitors using a synthesis-directed: De novo design model

The SARS-CoV-2 main viral protease (Mpro) is an attractive target for antivirals given its distinctiveness from host proteases, essentiality in the viral life cycle and conservation across coronaviridae. We launched the COVID Moonshot initiative to rapidly develop patent-free antivirals with open science and open data. Here we report the use of machine learning for de novo design, coupled with synthesis route prediction, in our campaign. We discover novel chemical scaffolds active in biochemical and live virus assays, synthesized with model generated routes. This journal is

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.

Scouting human A3 adenosine receptor antagonist binding mode using a molecular simplification approach: From triazoloquinoxaline to a pyrimidine skeleton as a key study

The concept of molecular simplification as a drug design strategy to shorten synthetic routes, while keeping or enhancing the biological activity of the lead drug, has been applied to design new classes of human A3 adenosine receptor (AR) antag