482639-32-7

Basic information

• Product Name: 2-CHLORO-5,7-DIMETHYL-3-QUINOLINECARBALDEHYDE
• Synonyms: 2-CHLORO-5,7-DIMETHYL-3-QUINOLINECARBALDEHYDE;AKOS BB-7562;2-CHLORO-5,7-DIMETHYL-QUINOLINE-3-CARBALDEHYDE;2-CHLORO-5,7-DIMETHYLQUINOLINE-3-CARBOXALDEHYDE
• CAS NO: 482639-32-7
• Molecular Formula: C₁₂H₁₀ClNO
• Molecular Weight: 219.67
• Mol File: 482639-32-7.mol

Chemical Properties

• Boiling Point: 365.4 °C at 760 mmHg
• Flash Point: 174.8 °C
• Appearance: /
• Density: 1.27 g/cm³
• Vapor Pressure: 1.57E-05mmHg at 25°C
• Refractive Index: 1.655
• CAS DataBase Reference: 2-CHLORO-5,7-DIMETHYL-3-QUINOLINECARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-5,7-DIMETHYL-3-QUINOLINECARBALDEHYDE(482639-32-7)
• EPA Substance Registry System: 2-CHLORO-5,7-DIMETHYL-3-QUINOLINECARBALDEHYDE(482639-32-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 482639-32-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Chloro-5,7-dimethyl-3-quinolinecarbaldehyde is used as a key reactant for the synthesis of isoxazolo[5,4-b]quinoline derivatives and 2-chloroquinolinyl-4-quinolinones. These synthesized compounds have potential applications in the development of new drugs and pharmaceutical agents, particularly those targeting various diseases and conditions.
Used in Chemical Research:
In the field of chemical research, 2-chloro-5,7-dimethyl-3-quinolinecarbaldehyde serves as an important building block for the creation of novel chemical entities. Its unique structure allows for further functionalization and modification, leading to the discovery of new compounds with potential applications in various industries, including pharmaceuticals, materials science, and agrochemicals.

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

Upstream product

• 2050-45-5 N-acetyl-3,5-dimethylaniline 
• 108-69-0 3,5-dimethylaminoaniline 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 1309388-96-2 2-(2,4-dichlorophenylthio)-5,7-dimethylquinoline-3-carbaldehyde 
• 1309389-13-6 methyl 2-((2-(2,4-dichlorophenylthio)-5,7-dimethylquinolin-3-yl)(hydroxy)methyl)acrylate 
• 1309388-97-3 5,7-dimethyl-2-(p-tolylthio)quinoline-3-carbaldehyde 
• 1591873-26-5 C₃₅H₃₀N₂O₄ 
• 1591873-52-7 C₃₆H₃₀N₂O₄ 
• 1591873-49-2 C₃₅H₂₉ClFN₃O₃ 
• 1591873-48-1 C₃₆H₃₃N₃O₃ 
• 1591873-47-0 C₃₅H₃₁N₃O₃ 
• 606101-83-1 N-(2-((3-cyano-5,7-dimethylquinolin-2-yl)amino)ethyl)-3-methoxybenzamide 
• 917747-10-5 2-chloro-5,7-dimethylquinoline-3-carbonitrile 
• 1356485-81-8 C₁₂H₁₁ClN₂O 
• 1356485-97-6 N-(3-(3-cyano-5,7-dimethylquinolin-2-ylamino)propyl)-4-methoxybenzamide 
• 1356485-96-5 N-(3-(3-cyano-5,7-dimethylquinolin-2-ylamino)propyl)-3-methoxybenzamide 
• 1356485-95-4 N-(3-(3-cyano-5,7-dimethylquinolin-2-ylamino)propyl)-2-methoxybenzamide 

Relevant articles and documents

Enantioselective synthesis of functionalized 1,4-dihydropyrazolo-[4′,3′:5,6]pyrano[2,3-: B] quinolines through ferrocenyl-phosphine-catalyzed annulation of modified MBH carbonates and pyrazolones

An enantioselective synthesis of highly functionalized 1,4-dihydropyrazolo[4′,3′:5,6]pyrano[2,3-b]quinolines from modified MBH carbonates and pyrazolones via a chiral phosphine-mediated alkylation/annulation sequence has been realized. The chiral dihydropyrano[2,3-c]pyrazoles bearing bio-active condensed heterocycles were facilely formed in good chemical yields and with high to excellent enantioselectivity by utilizing low catalyst loading.

Design, synthesis and biological evaluation of mono- and bisquinoline methanamine derivatives as potential antiplasmodial agents

Several classes of antimalarial drugs are currently available, although issues of toxicity and the emergence of drug resistant malaria parasites have reduced their overall therapeutic efficiency. Quinoline based antiplasmodial drugs have unequivocally been long-established and continue to inspire the design of new antimalarial agents. Herein, a series of mono- and bisquinoline methanamine derivatives were synthesised through sequential steps; Vilsmeier-Haack, reductive amination, and nucleophilic substitution, and obtained in low to excellent yields. The resulting compounds were investigated for in vitro antiplasmodial activity against the 3D7 chloroquine-sensitive strain of Plasmodium falciparum, and compounds 40 and 59 emerged as the most promising with IC50 values of 0.23 and 0.93 μM, respectively. The most promising compounds were also evaluated in silico by molecular docking protocols for binding affinity to the {0 0 1} fast-growing face of a hemozoin crystal model.

Transition-metal-free oxidative cyclization reaction of enynals to access pyrane-2-one derivatives

A novel and efficient metal-free C-H functionalization of enynals is developed to synthesize α-pyrone derivatives via the formation of two C-O bonds. In this project, K2S2O8 has been introduced as an efficient oxygen source and C-H functionalization agent in regioselective oxidative cyclization reaction with a relatively broad substrate scope.

Coupling-Isomerization-Cycloisomerization Reaction (CICIR) – An Unexpected and Efficient Domino Approach to Luminescent 2-(Hydroxymethylene)indenones

A Pd/Cu-catalyzed base mediated domino process of ortho-halo (hetero)aryl carboxaldehydes and propargyl alcohols unexpectedly furnish 2-(hydroxymethylene)indenones in good to excellent yield as a result of a coupling-isomerization-cycloisomerization reaction (CICIR). In addition, the title compounds constitute an interesting class of luminophores with tunable emission solvatochromicity.

Synthesis of new 3-(2-Chloroquinolin-3-yl)-5-phenylisoxazole derivatives via click chemistry approach

Herein, we report the synthesis of new substituted 3-(2-chloroquinolin-3- yl)-5-phenylisoxazole (3a-j) by click chemistry in good to moderate yields. This approach is based on the regioselective copper(I)-catalyzed cycloaddition between different nitrile oxides derived from 2-chloroquinoline- 3-carbaldehyde (2a-j) and phenylacetylene. Finally these derivatives were screened for their antibacterial evaluation in vitro against three Gram-negative clinical bacteria: Escherichia coli, Pseudomonas aeruginosa and Acinetobacter baumannii using standard methods.

Efficient synthesis of novel pyranoquinoline derivatives from simple acetanilide derivatives: Experimental and theoretical study of their physicochemical properties using DFT calculations

A convenient reaction of 2-chloroquinoline-3-carbaldehyde derivatives and dimedone in the presence of KF-Al2O3 for the synthesis of useful pyranoquinolines is described. Reasonable yields (41-50percent), easily available starting materials and less expensive efficient catalyst are the key features of the present method. A mechanism was proposed for the reaction course. Attribution of the chemical shifts was made with the help of the density functional theory (DFT) calculations. The computed nuclear magnetic resonance (NMR) chemical shifts are in good agreement with available experimental data. The nucleus-independent chemical shift (NICS) values were used as quantitative measures for the relative aromatic character in pyranoquinolines. The calculated NICS values obtained for the phenyl group of pyranoquinoline compounds are smaller than that of benzene. ?2014 Sociedade Brasileira de Qui?mica.

CYANOQUINOLINE COMPOUNDS HAVING ACTIVITY IN CORRECTING MUTANT-CFTR PROCESSING AND INCREASING ION TRANSPORT AND USES THEREOF

The present disclosure provides pharmaceutical compositions, pharmaceutical preparations and methods for increasing activity of a mutant cystic fibrosis transmembrane conductance regulator protein (mutant-CFTR). The pharmaceutical compositions, pharmaceut

Structure-activity relationships of cyanoquinolines with corrector-potentiator activity in Δf508 cystic fibrosis transmembrane conductance regulator protein

Cystic fibrosis (CF) is caused by mutations in the cystic fibrosis transmembrane conductance regulator (CFTR) chloride channel. The most common CF-causing mutation, ΔF508-CFTR, produces CFTR loss-of-function by impairing its cellular targeting to the plas

Cyanoquinolines with independent corrector and potentiator activities restore ΔPhe508-cystic fibrosis transmembrane conductance regulator chloride channel function in cystic fibrosis

The ΔPhe508 mutation in the cystic fibrosis transmembrane conductance regulator (CFTR) protein impairs its folding, stability, and chloride channel gating. Although small molecules that separately correct defective ΔPhe508-CFTR folding/cellular processing

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.