38101-91-6

Usage

Uses

Used in Biochemical and Cell Biology Research:
(E)-2-(4-Chlorostyryl)quinoline is used as a staining agent for visualizing and tracking cellular components such as DNA, mitochondria, and endoplasmic reticulum. Its fluorescent properties allow researchers to observe these structures and processes more effectively.
Used in Organic Light-Emitting Diodes (OLEDs) and Optoelectronic Devices:
(E)-2-(4-Chlorostyryl)quinoline is used as a light-emitting component in OLEDs and other optoelectronic devices due to its ability to emit light when excited, making it a potential candidate for these applications.
Used in Pharmaceutical Research:
(E)-2-(4-Chlorostyryl)quinoline is studied for its potential as an anti-cancer agent, with research being conducted to explore its pharmacological properties and possible applications in cancer treatment.

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 
• 1780-19-4 1,2,3,4-tetrahydro-2-methylquinoline 
• 873-76-7 para-Chlorobenzyl alcohol 
• 105-13-5 4-Methoxybenzyl alcohol 
• 91-22-5 quinoline 
• 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 

Relevant academic research and scientific papers

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

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.

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

Deaminative Olefination of Methyl N-Heteroarenes by an Amine Oxidase Inspired Catalyst

We explored the bioinspired o-quinone cofactor catalyzed aerobic primary amine dehydrogenation for a cascade olefination reaction with nine different methyl N-heteroarenes, including pyrimidines, pyrazines, pyridines, quinolines, quinoxolines, benzimidazoles, benzoxazoles, benzthiazoles, and triazines. An o-quinone catalyst phd (1,10-phenanthroline-5,6-dione) combined with a Br?nsted acid catalyzed the reaction. N-Heteroaryl stilbenoids were synthesized in high yields and (E)-selectivities under mild conditions using oxygen (1 atm) as the sole oxidant without needing transition-metal salt, ligand, stoichiometric base, or oxidant.

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.

MnO2 mediated sequential oxidation/olefination of alkyl-substituted heteroarenes with alcohols

A practical and efficient ligand-free MnO2 mediated sequential oxidation and olefination has been developed for the facile synthesis of a broad range of unsaturated N-heteroazaarenes from simple alkyl-substituted heteroarenes and alcohols. The procedure tolerates a series of functional groups, such as methoxyl, chloro, bromo, iodo, vinyl, phenolic and hetero groups, providing the olefination products in moderate to good yields.The protocol could be conducted at mild conditions and used environmentally friendly air as the clear oxidant.

Iron/TEMPO-catalyzed direct aerobic oxidative coupling of methyl-mubstituted N-heteroazaarenes with alcohols

A novel direct oxidative coupling of methyl-substituted N-heteroazaarenes with alcohols has been developed to construct olefins under mild condition. The reaction is catalyzed by Fe(NO3)3·9H2O/TEMPO with oxygen as terminal oxidant. A variety of E-disubstituted olefins bearing diverse functional groups could be obtained selectively in moderate to excellent yields. The reaction is environmentally friendly and ligand-free.

Preparation method of trans-disubstituted olefin

The invention relates to the technical field of organic chemical synthesis, and in particular, relates to a preparation method of trans-disubstituted olefin. According to the preparation method, primary alcohol and methyl azacycle are taken as raw materials, transition metal salt, nitric oxide and alkali are taken as catalysts, an organic solution is taken as a reaction medium, and reaction is carried out in an oxygen atmosphere. According to the preparation method, a reaction by-product is only water, the environment is not polluted, the required transition metal catalyst is cheap and easy toobtain, the reaction does not need high temperature, and the reaction cost and the requirements on reaction conditions can be reduced.

NaCl as Catalyst and Water as Solvent: Highly E-Selective Olefination of Methyl Substituted N-Heteroarenes with Benzyl Amines and Alcohols

Oxidative coupling of benzylamines and alcohols with methyl substituted N-heteroarenes such as quinolines and quinoxalines has been achieved using chloride, a sea abundant anion as the catalyst for practical synthesis of a wide range of E-disubstituted olefins in aqueous medium. Detailed mechanistic studies and control experiments were carried out to deduce the reaction mechanism which indicated that in situ formed ClO2- is the active form of the catalyst. We have successfully carried out a 1 g scale reaction using this methodology, and five pharmaceutically relevant conjugated olefins were also synthesized by this method in moderate to good yields.