16032-40-9

Basic information

• Product Name: 2-(4-METHOXYPHENYL)QUINOLINE
• Synonyms: 2-(4-METHOXYPHENYL)QUINOLINE;METHYL 4-(2-QUINOLINYL)PHENYL ETHER;2-(p-Methoxyphenyl)quinoline
• CAS NO: 16032-40-9
• Molecular Formula: C₁₆H₁₃NO
• Molecular Weight: 235.28
• Mol File: 16032-40-9.mol
• Article Data: 177

Chemical Properties

• Melting Point: 122-124℃
• Boiling Point: 398℃
• Flash Point: 144℃
• Appearance: /
• Density: 1.141
• PKA: 4.76±0.30(Predicted)
• CAS DataBase Reference: 2-(4-METHOXYPHENYL)QUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-METHOXYPHENYL)QUINOLINE(16032-40-9)
• EPA Substance Registry System: 2-(4-METHOXYPHENYL)QUINOLINE(16032-40-9)

Safety Data

• Hazardous Substances Data: 16032-40-9(Hazardous Substances Data)

Usage

Description

2-(4-Methoxyphenyl)quinoline, a quinoline derivative with the molecular formula C17H13NO, features a methoxyphenyl group attached to the 2-position of the quinoline ring. This chemical compound has garnered attention for its potential biological activities, such as antibacterial and antitumor properties, along with its utility as a fluorescent dye in bioimaging and chemical sensing applications. Its unique structural and pharmacological attributes render it a promising candidate for exploration in medicinal chemistry and materials science.

Uses

Used in Pharmaceutical Industry:
2-(4-Methoxyphenyl)quinoline is used as a pharmaceutical agent for its demonstrated antibacterial properties, offering a potential alternative for treating bacterial infections. Its antitumor capabilities also position it as a candidate for further research in oncology, where it could contribute to the development of novel cancer therapies.
Used in Bioimaging Applications:
As a fluorescent dye, 2-(4-Methoxyphenyl)quinoline is utilized in bioimaging to visualize and track cellular processes and structures. Its fluorescence properties allow researchers to monitor biological phenomena in real-time, enhancing the understanding of cellular dynamics and mechanisms.
Used in Chemical Sensing Applications:
2-(4-Methoxyphenyl)quinoline serves as a chemical sensor, detecting and responding to specific analytes in various environments. Its sensitivity and selectivity make it a valuable tool in analytical chemistry for environmental monitoring, medical diagnostics, and other fields requiring precise detection of chemical species.

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 62-53-3 aniline 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 148564-94-7 2-[3-hydroxy-3-(p-methoxyphenyl)prop-1-ynyl]trifluoroacetanilide 
• 221909-90-6 3-(2-aminophenyl)-1-(4-methoxyphenyl)prop-2-yn-1-one 
• 73031-42-2 1-(1-pyrrolidinyl)-1-(4-methoxyphenyl)ethene 
• 253-83-8 1,2,3-benzotriazine 
• 7647-01-0 hydrogenchloride 
• 22396-06-1 1-(4-methoxyphenyl)-3-(2-nitrophenyl)-2-propen-1-one 
• 64-19-7 acetic acid 
• 10034-85-2 hydrogen iodide 
• 1021684-82-1 (E)-1-(4-methoxyphenyl)-3-(2-nitrophenyl)prop-2-en-1-one 
• 5344-90-1 2-Aminobenzyl alcohol 
• 100-06-1 1-(4-methoxyphenyl)ethanone 

Downstream Products

• 246181-55-5 1-methyl-2-(4’-methoxyphenyl)-1H-4-quinolone 
• 109030-96-8 2-(4-hydroxyphenyl)-1-methylquinolin-4(1H)-one 
• 27382-42-9 1-(2-phenoxy-ethyl)-1H-quinolin-2-one 
• 1198359-38-4 2-(4-methoxyphenyl)quinoline hydrobromide 
• 1236385-08-2 4-chloro-2-(4-methoxyphenyl)-1,2-dihydroquinoline-1,3-dicarbaldehyde 
• 1448448-96-1 2-(4-methoxy-2-(5-methylthiophen-2-yl)phenyl)quinoline 
• 1662702-34-2 8-iodo-2-(3-iodo-4-methoxyphenyl)quinoline 
• 36710-31-3 2-(4-methoxylphenyl)quinoline N-oxide 

Relevant articles and documents

Pr2O3 Supported Nano-layered Ruthenium Catalyzed Acceptorless Dehydrogenative Synthesis of 2-Substituted Quinolines and 1,8-Naphthyridines from 2-Aminoaryl Alcohols and Ketones

Pr2O3 supported Ru nanolayers and Ru nanoparticles catalysts were examined for the synthesis of quinolines. The Ru nanolayer was most active catalyst and showed a broad substrate scope. Structure-activity relationship demonstrated that the metallic state and morphology of Ru as well as the basic site of Pr2O3 were indispensable factors of this catalytic system.

A copper(II)-catalyzed protocol for modified Friedl?nder quinoline synthesis

2-Aminobenzyl alcohol reacts with an array of ketones in dioxane at 100 °C in the presence of a catalytic amount of CuCl2 along with KOH under O2 atmosphere to afford the corresponding quinolines in good yields. 2-Aminobenzyl alcohol is also oxidatively coupled and cyclized with various aldehydes by step-by-step procedure, an initial treatment of 2-aminobenzyl alcohol in the presence of CuCl2 and KOH in dioxane under O2 atmosphere and subsequent addition of aldehyde to the mixture followed by stirring under argon atmosphere, to give 3-substituted quinolines in moderate to good yields.

The Diverse One-Pot Reactions of 2-Quinolylzincates: Homologation, Electrophilic Trapping, Hydroxylation, and Arylation Reactions

2-Quinolylzincates were efficiently produced from the regioselective metalation reactions of quinoline with various organozincates as key intermediates. The four different types of title reactions of these intermediates under the presented reaction conditions allowed for the facile formation of the corresponding C-2 functionalized quinolines, which are not successfully accessed through typical zincation methods.

Samarium diiodide mediated reductive coupling of 2-nitro-1,3-diphenyl-2-propen-1-one: Synthesis of quinolines

The intramolecular reductive cyclization of 2-nitro-1,3-diphenyl-2-propen-1-ones (1) induced by SmI2 was investigated and 2-arylquinolines (2) were obtained in moderate to good yields at room temperature under neutral conditions.

Multifunctional catalysis of a ruthenium-grafted hydrotalcite: One-pot synthesis of quinolines from 2-aminobenzyl alcohol and various carbonyl compounds via aerobic oxidation and aldol reaction

The Ru-grafted hydrotalcite was found to be an excellent multifunctional catalyst for one-pot synthesis of quinolines from 2-aminobenzyl alcohol and various carbonyl compounds. These quinolines were obtained through aerobic oxidation by the Ru species, followed by aldol reaction on base sites of the hydrotalcite.

Large-Scale Cobalt-Catalyzed Cross-Couplings of Functionalized Bench-Stable Arylzinc Pivalates with (Hetero)Aryl and Alkenyl Halides

A robust and scalable CoCl 2 -catalyzed cross-coupling between functionalized arylzinc pivalates and various electron-poor (hetero)aryl and alkenyl halides is reported.

Synthesis of Quinolines Through Acceptorless Dehydrogenative Coupling Catalyzed by Rhenium PN(H)P Complexes

A practical and sustainable synthesis of substituted quinolines was achieved through the annulation of 2-aminobenzyl alcohol with various secondary alcohols, ketones, aldehydes, or nitriles, under hydrogen-borrowing conditions. Under the catalysis of well-defined rhenium complexes bearing tridentate diphosphinoamino ligands, the reaction proceeded efficiently (31 examples were isolated with yields up to 96 %) affording a variety of quinoline derivatives.

A Domino Heck Coupling-Cyclization-Dehydrogenative Strategy for the One-Pot Synthesis of Quinolines

An efficient, one-pot, domino synthesis of quinolines via the coupling of iodoanilines with allylic alcohols facilitated by palladium catalysis is described. The overall synthetic process involves an intermolecular Heck coupling between 2-iodoanilines and allylic alcohols, intramolecular condensation of in situ generated ketones with an internal amine functional group, and a dehydrogenation sequence. Notably, this protocol occurs in water as a green solvent. Significantly, the method exhibits broad substrate scope and is applied for the synthesis of deuterated quinolines through a deuterium-exchange process.

Visible-Light-Mediated Oxidative Cyclization of 2-Aminobenzyl Alcohols and Secondary Alcohols Enabled by an Organic Photocatalyst

This paper describes a visible-light-mediated oxidative cyclization of 2-aminobenzyl alcohols and secondary alcohols to produce quinolines at room temperature. This photocatalytic method employed anthraquinone as an organic small-molecule catalyst and DMSO as an oxidant. According to this present procedure, a series of quinolines were prepared in satisfactory yields.