5392-19-8

Basic information

• Product Name: 2-[2-(4-chlorophenyl)ethenyl]quinoline
• Synonyms: alpha-(p-Chlorobenzylidene)-quinaldine
• CAS NO: 5392-19-8
• Molecular Formula: C₁₇H₁₂ClN
• Molecular Weight: 265.7369
• Mol File: 5392-19-8.mol
• Article Data: 33

Chemical Properties

• Boiling Point: 420°C at 760 mmHg
• Flash Point: 240.3°C
• Density: 1.253g/cm³
• Vapor Pressure: 7.12E-07mmHg at 25°C
• Refractive Index: 1.728
• CAS DataBase Reference: 2-[2-(4-chlorophenyl)ethenyl]quinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[2-(4-chlorophenyl)ethenyl]quinoline(5392-19-8)
• EPA Substance Registry System: 2-[2-(4-chlorophenyl)ethenyl]quinoline(5392-19-8)

Safety Data

• Hazardous Substances Data: 5392-19-8(Hazardous Substances Data)

Usage

Chemical Class

Quinolines

Derivation

4-chlorobenzaldehyde and aniline

Usage

Fluorescent dye, pharmaceutical intermediate

Molecular Structure

Quinoline core with a 4-chlorophenylethenyl group

Properties

Fluorescent, pharmaceutical

Applications

Synthesis of drugs targeting bacterial and protozoal infections, important compound in the pharmaceutical industry.

Upstream product

• 91-63-4 2-methylquinoline 
• 104-88-1 4-chlorobenzaldehyde 
• 3157-65-1 N-(p-chlorobenzylidene)-p-toluenesulfonamide 
• 4750-61-2 N-(p-chlorobenzyl)aniline 
• 104-86-9 4-chlorobenzylamine 
• 75-52-5 nitromethane 
• 30626-03-0 (3E)-4-(4-chlorophenyl)-3-buten-2-one 
• 552-89-6 2-nitro-benzaldehyde 
• 1073-67-2 4-vinylbenzyl chloride 
• 1613-37-2 Quinoline N-oxide 
• 873-76-7 para-Chlorobenzyl alcohol 
• 1780-19-4 1,2,3,4-tetrahydro-2-methylquinoline 
• 91-22-5 quinoline 
• 105-13-5 4-Methoxybenzyl alcohol 

Downstream Products

• 70391-37-6 (4-chlorophenyl)(quinolin-2-yl)methanone 

Relevant articles and documents

Nickel(II)-Catalyzed Selective (E)-Olefination of Methyl Heteroarenes Using Benzyl Alcohols via Acceptorless Dehydrogenative Coupling Reaction

An efficient catalytic protocol for the synthesis of selective (E)-olefins by the newly synthesized nickel complexes via greener acceptorless dehydrogenative coupling methodology is presented. Two nickel(II) N, S chelating complexes were structurally characterized with the aid of spectral and single crystal X-ray diffraction methods. Olefination of 2-methylheteroarenes with benzyl alcohols via acceptorless dehydrogenative coupling is achieved by inexpensive nickel(II) catalysts. The present olefination protocol is simple and furnishes the desired 2-alkenylheteroarenes in 35 h and yields in the range of 40–93 %. The dehydrogenative coupling reaction proceeds via the generation of an aldehyde intermediate and produces water and hydrogen as sole by-products. The wide substrate scope of this catalytic reaction covered the synthesis of drug intermediates.

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.