323196-71-0

Basic information

• Product Name: 2-CHLORO-5,8-DIMETHYL-3-QUINOLINECARBALDEHYDE
• Synonyms: AKOS BB-7558;2-CHLORO-5,8-DIMETHYL-3-QUINOLINECARBALDEHYDE;2-CHLORO-5,8-DIMETHYL-QUINOLINE-3-CARBALDEHYDE;2-CHLORO-5,8-DIMETHYLQUINOLINE-3-CARBOXALDEHYDE
• CAS NO: 323196-71-0
• Molecular Formula: C₁₂H₁₀ClNO
• Molecular Weight: 219.67
• Mol File: 323196-71-0.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 364.5°C at 760 mmHg
• Flash Point: 174.2°C
• Appearance: /
• Density: 1.27g/cm³
• Vapor Pressure: 1.68E-05mmHg at 25°C
• Refractive Index: 1.655
• CAS DataBase Reference: 2-CHLORO-5,8-DIMETHYL-3-QUINOLINECARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-5,8-DIMETHYL-3-QUINOLINECARBALDEHYDE(323196-71-0)
• EPA Substance Registry System: 2-CHLORO-5,8-DIMETHYL-3-QUINOLINECARBALDEHYDE(323196-71-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 323196-71-0(Hazardous Substances Data)

Usage

General Description

2-Chloro-5,8-dimethyl-3-quinolinecarbaldehyde is a chemical compound with the molecular formula C12H10ClNO. It is a yellow solid with a molecular weight of 225.67 g/mol. 2-CHLORO-5,8-DIMETHYL-3-QUINOLINECARBALDEHYDE is used in the synthesis of various pharmaceuticals and agrochemicals. It acts as an intermediate in the production of antimalarial drugs and has potential applications in the field of medicinal chemistry. Additionally, it is utilized as a reagent in organic synthesis and in the development of novel chemical compounds. However, it is important to handle this compound with care as it may pose hazards to human health and the environment.

InChI:InChI=1/C12H10ClNO/c1-7-3-4-8(2)11-10(7)5-9(6-15)12(13)14-11/h3-6H,1-2H3

Upstream product

• 95-78-3 2,5-Dimethylaniline 
• 2050-44-4 N-(2,5-dimethylphenyl)acetamide 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 1620844-73-6 (Z)-5-((2-chloro-6,8-dimethylquinolin-3-yl)methylene)-3-phenyl-2-thioxothiazolidin-4-one 

Relevant articles and documents

Efficient synthesis of 3-pyrrolylquinolines via an 1,3-dipolar cycloaddition/oxidation sequence

The synthesis of some new functionalized quinolyl derivatives relies on the 1,3-dipolar cycloaddition of an azomethine ylide, generated from sarcosine and paraformaldehyde, to quinolyl α,β-unsaturated esters, followed by oxidation of the pyrrolidinyl moiety to pyrrole with activated MnO2. Copyright Taylor & Francis, Inc.

Synthesis and Herbicidal Activity of Triketone-Quinoline Hybrids as Novel 4-Hydroxyphenylpyruvate Dioxygenase Inhibitors

4-Hydroxyphenylpyruvate dioxygenase (EC 1.13.11.27, HPPD) is one of the most important targets for herbicide discovery. In the search for new HPPD inhibitors with novel scaffolds, triketone-quinoline hybrids were designed and subsequently optimized on the basis of the structure-activity relationship (SAR) studies. Most of the synthesized compounds displayed potent inhibition of Arabidopsis thaliana HPPD (AtHPPD), and some of them exhibited broad-spectrum and promising herbicidal activity at the rate of 150 g ai/ha by postemergence application. Most promisingly, compound III-l, 3-hydroxy-2-(2-methoxy-7-(methylthio)quinoline-3-carbonyl)cyclohex-2-enone (Ki = 0.009 ～M, AtHPPD), had broader spectrum of weed control than mesotrione. Furthermore, compound III-l was much safer to maize at the rate of 150 g ai/ha than mesotrione, demonstrating its great potential as herbicide for weed control in maize fields. Therefore, triketone-quinoline hybrids may serve as new lead structures for novel herbicide discovery.

Synthesis and biological evaluation of new rhodanine analogues bearing 2-chloroquinoline and benzo[h]quinoline scaffolds as anticancer agents

Several rhodanine derivatives (9-39) were synthesized for evaluation of their potential as anticancer agents. Villsmeier cyclization to synthesize aza-aromatic aldehydes, rhodanine derivatives preparation and Knoevenagel type of condensation between the rhodanines and aza-aromatic aldehydes are key steps used for the synthesis of 31 compounds. In vitro antiproliferative activity of the synthesized rhodanine derivatives (9-39) was studied on a panel of six human tumor cell lines viz. HGC, MNK-74, MCF-7, MDAMB-231, DU-145 and PC-3 cell lines. Some of the compounds were capable of inhibiting the proliferation of cancer cell lines at a micromolar concentration. Six compounds are found to be potent against HGC cell lines; compound 15 is found to be active against HGC - Gastric, MCF7 - Breast Cancer and DU145 - Prostate Cancer cell lines; compound 39 is potent against MNK-74; four compounds are found to be potent against MCF-7 cell lines; three compounds are active against MDAMB-231; nine compounds are found to be potent against DU-145; three compounds are active against PC-3 cell lines. These compounds constitute a promising starting point for the development of novel and more potent anticancer agents in future.