38101-69-8

Basic information

• Product Name: 2-(2-phenylethenyl)quinoline
• CAS NO: 38101-69-8
• Molecular Formula: C₁₇H₁₃N
• Molecular Weight: 231.2918
• Mol File: 38101-69-8.mol
• Article Data: 54

Chemical Properties

• Boiling Point: 387°C at 760 mmHg
• Flash Point: 168.7°C
• Density: 1.156g/cm³
• Vapor Pressure: 7.58E-06mmHg at 25°C
• Refractive Index: 1.727
• CAS DataBase Reference: 2-(2-phenylethenyl)quinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-phenylethenyl)quinoline(38101-69-8)
• EPA Substance Registry System: 2-(2-phenylethenyl)quinoline(38101-69-8)

Safety Data

• Hazardous Substances Data: 38101-69-8(Hazardous Substances Data)

Usage

Chemical class

Quinoline derivatives

Structural feature

Quinoline core with a phenylethene group attached to the 2-position

Potential biological activity

Yes

Use as a ligand

Yes, in coordination chemistry

Possible applications

Organic synthesis and medicinal chemistry

Interesting for further research

Yes, due to its properties and potential uses.

Upstream product

• 588-72-7 [(E)-2-bromoethenyl]benzene 
• 91-63-4 2-methylquinoline 
• 1221065-98-0 C₂₃H₃₉NO₂S 
• 73845-05-3 N-methanesulfonyl benzylideneamine 
• 13909-34-7 N-benzylidenephenylsulfonamide 
• 51608-60-7 N-(benzylidene)-p-methylbenzenesulfonamide 
• 14674-28-3 N-benzylidene-2-methylbenzenesulfonamide 
• 14674-32-9 N-Benzyliden-3-nitrobenzolsulfonamid 
• 780-25-6 N-benzylidene benzylamine 
• 52960-60-8 N-benzylidene-4-methoxy-benzenesulfonamide 
• 148838-27-1 N-2,4,6-trimethylphenylsulfonylbenzaldimine 
• 1218989-07-1 4-methyl-N-(1-phenyl-2-(quinolin-2-yl)ethyl)benzenesulfonamide 
• 38101-94-9 rac-1-phenyl-2-(quinolin-2-yl)ethanol 
• 16118-22-2 benzylidenamine 

Downstream Products

• 81340-59-2 2,2'-- (2-phenylpropane-1,3-diyl)diquinoline 
• 116030-17-2 1-[2]quinolyl-3-[4]quinolyl-2-phenyl-propane 
• 411239-46-8 2-(2,2-diphenyl-ethyl)-quinoline 
• 1613-41-8 2-phenethyl-quinoline 
• 93-10-7 quinoline-2-carboxylic acid 
• 94463-24-8 2-((αRS,βSR)-α,β-dibromo-phenethyl)-quinoline 
• 80998-91-0 (Z)-2-styrylquinoline 
• 122649-44-9 1,1'-dimethyl-2,2'-(2-phenyl-propanediyl)-bis-quinolinium; iodide 
• 101583-63-5 2-(2-phenylethyl)-1,2,3,4-tetrahydroquinoline 
• 132494-28-1 1-methyl-2-phenethyl-quinolinium; iodide 
• 94463-24-8 2-(α,β-dibromo-phenethyl)-quinoline 

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.

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.