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

Downstream Products

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

Relevant articles and documents

Ru(II)–NNO pincer-type complexes catalysed E-olefination of alkyl-substituted quinolines/pyrazines utilizing primary alcohols

An efficient and selective E-olefination of alkyl-substituted quinolines and pyrazines through acceptorless dehydrogenative coupling of alcohols catalysed by Ru(II)–N^N^O pincer-type complexes encompassing carbonyl and triphenylarsines as co-ligands is de

Waste-minimized synthesis of C2 functionalized quinolines exploiting iron-catalysed C-H activation

Herein we present an efficient and regioselective iron-catalyzed methodology for the external oxidant-free functionalization of quinoline-N-oxides. The protocol, based on the use of inexpensive and easily accessible FeSO4, showed broad applicability to a wide range of substrates. An additional green feature of this synthetic methodology is H2O being the only by-product. Experimental and computational investigations provide support to a mechanism based on a facile C-H activation event. The green efficiency of the process has also been carefully assessed using: (i) metrics related to the synthetic process (AE, Yield, 1/SF, MRP and RME); (ii) safety/hazard metrics (SHZI and SHI); and (iii) metrics related to the metal used as the catalyst (Abundance, OEL and ADP). In addition to the many advantages of this protocol related to the green iron catalyst used and the safety/hazard features of the process, an E-factor value of ca. 0.92 (84 to >99% reduction compared to known protocols) evidently confirms the sustainable efficiency of the procedure presented. Practical utility has also been demonstrated by performing the reaction efficiently on a multi-gram scale. This journal is

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.