14174-62-0

Basic information

• Product Name: 2-[(E)-2-(2-chlorophenyl)ethenyl]quinoline
• CAS NO: 14174-62-0
• Molecular Formula: C₁₇H₁₂ClN
• Molecular Weight: 265.7369
• Mol File: 14174-62-0.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 417.3°C at 760 mmHg
• Flash Point: 238.6°C
• Density: 1.253g/cm³
• Vapor Pressure: 8.7E-07mmHg at 25°C
• Refractive Index: 1.728
• CAS DataBase Reference: 2-[(E)-2-(2-chlorophenyl)ethenyl]quinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[(E)-2-(2-chlorophenyl)ethenyl]quinoline(14174-62-0)
• EPA Substance Registry System: 2-[(E)-2-(2-chlorophenyl)ethenyl]quinoline(14174-62-0)

Safety Data

• Hazardous Substances Data: 14174-62-0(Hazardous Substances Data)

Usage

Chemical Family

Quinoline family

Physical Appearance

Yellow crystalline solid

Molecular Weight

265.73 g/mol

Structural Feature

Quinoline ring

Substituent

2-chlorophenyl group at position 2

Ethenyl Group

At position 2 in the E configuration

Potential Applications

Organic synthesis and pharmaceutical research

Precaution

Hazardous effects if not used properly

Upstream product

• 91-63-4 2-methylquinoline 
• 89-98-5 2-chloro-benzaldehyde 
• 135822-90-1 o-chloro-N-tosylbenzaldimine 
• 41001-24-5 N-(2-chlorobenzyl)aniline 
• 89-97-4 2-CHLOROBENZYLAMINE 
• 91-22-5 quinoline 
• 1613-37-2 Quinoline N-oxide 
• 2039-87-4 2-chlorostyrene 
• 17849-38-6 2-Chlorobenzyl alcohol 

Relevant articles and documents

Metal-Free Synthesis of Alkenylazaarenes and 2-Aminoquinolines through Base-Mediated Aerobic Oxidative Dehydrogenation of Benzyl Alcohols

A metal-free, base-mediated, and atom-efficient oxidative dehydrogenative coupling of substituted phenylmethanols (benzyl alcohols) with methyl azaarenes or phenylacetonitriles to afford substituted alkenylazaarenes or 2-aminoquinolines, respectively is described. CsOH.H2O was discovered to be the base of choice for obtaining optimal yields of the title compounds, although the reaction could proceed with KOH as well. The protocol that works efficiently in the presence of air is amenable over broad range of substrates.

NH4I-mediated sp3 C-H cross-dehydrogenative coupling of benzylamines with 2-methylquinoline for the synthesis of E-2-styrylquinolines

Without any metal catalyst, a simple and efficient method for the synthesis of E-2-styrylquinolines through sp3 C-H cross-dehydrogenative coupling of benzylamines with 2-methylquinolines mediated by NH4I under air is successfully developed. The oxidative olefination proceeded through deamination and sp3 C–H bond activation. A plausible mechanism is proposed for the construction of E-2-styrylquinolines.

Malononitrile-activated synthesis and anti-cholinesterase activity of styrylquinoxalin-2(1: H)-ones

Herein, we report a base-free malononitrile activated condensation of 3-methylquinoxaline-2(1H)-one (3MQ) 1 with aryl aldehydes 3a-3ad for synthesis of styrylquinoxalin-2(1H)-ones (SQs) 4a-4ad with excellent yields. In this reaction, malononitrile activates the aldehyde via Knoevenagel condensation towards reaction with 3MQ 1 and gets liberated during the course of reaction to yield the desired SQs 4a-4ad. The SQs were evaluated for in vitro cholinesterase inhibition and 4n was found to display a mixed type of inhibition of AChE, which was supported by molecular modelling studies. This study has led to the discovery of a new chemotype for cholinesterase inhibition which might be useful in finding a remedy for Alzheimer's disease.