40941-53-5

Basic information

• Product Name: 7-chloro-4-methylquinoline
• Synonyms: 7-chloro-4-methylquinoline;4-Methyl-7-chloroquinoline
• CAS NO: 40941-53-5
• Molecular Formula: C₁₀H₈ClN
• Molecular Weight: 177.63022
• EINECS: 255-147-5
• Mol File: 40941-53-5.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 294.2°Cat760mmHg
• Flash Point: 159.6°C
• Appearance: /
• Density: 1.225g/cm³
• Vapor Pressure: 0.00289mmHg at 25°C
• Refractive Index: 1.634
• CAS DataBase Reference: 7-chloro-4-methylquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 7-chloro-4-methylquinoline(40941-53-5)
• EPA Substance Registry System: 7-chloro-4-methylquinoline(40941-53-5)

Safety Data

• Hazardous Substances Data: 40941-53-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H8ClN/c1-7-4-5-12-10-6-8(11)2-3-9(7)10/h2-6H,1H3

Upstream product

• 6607-66-5 1,3,3-trimethoxybutane 
• 141-85-5 3-chloroaniline hydrochloride 
• 78-94-4 methyl vinyl ketone 
• 108-42-9 3-chloro-aniline 
• 86-98-6 4,7-dichloroquinoline 
• 75-16-1 methylmagnesium bromide 
• 121714-78-1 iron(III) chloride hexahydrate 
• 18826-95-4 1.3-butanediol 

Downstream Products

• 476472-18-1 2-(7-chloro-quinolin-4-yl)-1-pyridin-2-yl-ethanone 
• 476472-19-2 2-(7-chloro-quinoline-4-yl)-1-(6-methyl-pyridin-2-yl)-ethanone 
• 476473-26-4 1-[2-(7-Chloro-quinolin-4-yl)-1-pyridin-2-yl-eth-(E)-ylideneamino]-pyrrolidin-2-one 
• 476473-27-5 1-[2-(7-Chloro-quinolin-4-yl)-1-(6-methyl-pyridin-2-yl)-eth-(E)-ylideneamino]-pyrrolidin-2-one 
• 13337-66-1 7-chloroquinoline-4-carboxylic acid 

Relevant articles and documents

Synthesis and biological evaluation of benzhydryl-based antiplasmodial agents possessing Plasmodium falciparum chloroquine resistance transporter (PfCRT) inhibitory activity

Due to the surge in resistance to common therapies, malaria remains a significant concern to human health worldwide. In chloroquine (CQ)-resistant (CQ-R) strains of Plasmodium falciparum, CQ and related drugs are effluxed from the parasite's digestive vacuole (DV). This process is mediated by mutant isoforms of a protein called CQ resistance transporter (PfCRT). CQ-R strains can be partially re-sensitized to CQ by verapamil (VP), primaquine (PQ) and other compounds, and this has been shown to be due to the ability of these molecules to inhibit drug transport via PfCRT. We have previously developed a series of clotrimazole (CLT)-based antimalarial agents that possess inhibitory activity against PfCRT (4a,b). In our endeavor to develop novel PfCRT inhibitors, and to perform a structure-activity relationship analysis, we synthesized a new library of analogues. When the benzhydryl system was linked to a 4-aminoquinoline group (5a-f) the resulting compounds exhibited good cytotoxicity against both CQ-R and CQ-S strains of P. falciparum. The most potent inhibitory activity against the PfCRT-mediated transport of CQ was obtained with compound 5k. When compared to the reference compound, benzhydryl analogues of PQ (5i,j) showed a similar activity against blood-stage parasites, and a stronger in vitro potency against liver-stage parasites. Unfortunately, in the in vivo transmission blocking assays, 5i,j were inactive against gametocytes.

Dearomative Photocatalytic Construction of Bridged 1,3-Diazepanes

The construction of diverse sp3-rich skeletal ring systems is of importance to drug discovery programmes and natural product synthesis. Herein, we report the photocatalytic construction of 2,7-diazabicyclo[3.2.1]octanes (bridged 1,3-diazepanes) via a reductive diversion of the Minisci reaction. The fused tricyclic product is proposed to form via radical addition to the C4 position of 4-substituted quinoline substrates, with subsequent Hantzsch ester-promoted reduction to a dihydropyridine intermediate which undergoes in situ two-electron ring closure to form the bridged diazepane architecture. A wide scope of N-arylimine and quinoline derivatives was demonstrated and good efficiency was observed in the construction of sterically congested all-carbon quaternary centers. Computational and experimental mechanistic studies provided insights into the reaction mechanism and observed regioselectivity/diastereoselectivity.

Quinolines synthesis by reacting 1,3-butanediol with anilines in the presence of iron catalysts

2-, 4-, 6-, 7-, and 8-substituted quinolines were synthesized in 78–95% yield by the reaction of 1,3- butanediol with anilines in the presence of iron catalysts in carbon tetrachloride.