5396-94-1

Usage

Uses

Used in Organic Synthesis:
2-[2-(4-bromophenyl)ethenyl]quinoline is used as a building block in the synthesis of other organic compounds, leveraging its chemical reactivity and structural features to create a wide range of molecules with diverse applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-[2-(4-bromophenyl)ethenyl]quinoline is used as a starting material for the development of new drugs. Its bioactive properties and interactions with biological targets make it a promising candidate for drug discovery and the treatment of various diseases.
Used in Materials Science:
2-[2-(4-bromophenyl)ethenyl]quinoline is utilized in materials science for its potential applications in the development of new materials with specific properties, such as光电材料 (photoelectric materials), 光催化剂 (photocatalysts), and 有机半导体 (organic semiconductors).
Used as a Fluorescent Probe in Biochemical and Cellular Studies:
2-[2-(4-bromophenyl)ethenyl]quinoline serves as a fluorescent probe in biochemical and cellular studies, allowing researchers to track and visualize specific biological processes and interactions due to its fluorescent properties.

InChI:InChI=1/C17H12BrN/c18-15-9-5-13(6-10-15)7-11-16-12-8-14-3-1-2-4-17(14)19-16/h1-12H

Upstream product

• 91-63-4 2-methylquinoline 
• 1122-91-4 4-bromo-benzaldehyde 
• 1780-19-4 1,2,3,4-tetrahydro-2-methylquinoline 
• 91-22-5 quinoline 
• 1613-37-2 Quinoline N-oxide 
• 873-75-6 4-bromobenzenemethanol 
• 2039-82-9 1-bromo-4-ethenyl-benzene 

Downstream Products

• 1246638-67-4 (E)-2-[2-(4'-methyl-[1,1'-biphenyl]-4-yl)vinyl]quinoline 
• 1246638-70-9 (E)-2-[2-(4'-chloro-[1,1'-biphenyl]-4-yl)vinyl]quinoline 
• 1246638-68-5 (E)-2-[2-(4'-methoxy-[1,1'-biphenyl]-4-yl)vinyl]quinoline 
• 190437-73-1 (E)-2-[2-([1,1'-biphenyl]-4-yl)vinyl]quinoline 

Relevant academic research and scientific papers

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

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.

Nickel-Catalyzed Direct Alkenylation of Methyl Heteroarenes with Primary Alcohols

An efficient nickel-catalyzed acceptorless dehydrogenative coupling of methyl-substituted heteroarenes with primary alcohols is achieved using an in situ generated complex of inexpensive NiBr2 and readily available 8-aminoquinoline picolinic amide ligand. The protocol is operationally simple and scalable and furnishes a series of high-value 2-alkenylheteroarenes in good yields (up to 88percent) with exclusive E-selectivity. The reaction proceeds with the release of water and molecular hydrogen, which was analyzed through gas chromatography to validate the reaction mechanism. ?

Direct Alkenylation of 2-Methylquinolines with Aldehydes through Synergistic Catalysis of 1,3-Dimethylbarbituric Acid and HOAc

An efficient and practical direct alkenylation of 2-methylquinolines with aldehydes has been achieved through a novel synergistic organocatalysis. The HOAc- activated 2-methylquiolines undergo a Michael addition to 1,3-dimethylbarbituric acid-activated aldehydes, followed by a retro-Michael addition to release 1,3-dimethylbarbituric acid and the target products. The transformation produced various 2-alkenylquinolines with good to excellent yields and featured mild reaction conditions, atom- and step-economy, good functional group tolerance, and operational simplicity. (Figure presented.).

Manganese-Catalyzed Dehydrogenative Alkylation or α-Olefination of Alkyl-Substituted N-Heteroarenes with Alcohols

Catalysis with earth-abundant transition metals is an option to help save our rare noble-metal resources and is especially interesting when novel reactivity or selectivity patterns are observed. We report here on a novel reaction, namely the dehydrogenative alkylation or α-olefination of alkyl-substituted N-heteroarenes with alcohols. Manganese complexes developed in our laboratory catalyze the reaction with high efficiency whereas iron and cobalt complexes stabilized by the same ligands are essentially inactive. Hydrogen is liberated during the reaction, and bromine and iodine functional groups as well as olefins are tolerated. A variety of alkyl-substituted N-heteroarenes can be functionalized, and benzylic and aliphatic alcohols undergo the reaction.

A trans-substituted olefin preparation method (by machine translation)

This invention relates to a trans-substituted olefin preparation method, which belongs to the technical field of organic chemical synthesis. The method adopts the simple alcohol and methyl nitrogen-containing heterocyclic as the starting material, by transition metal-catalyzed alkene base reaction, to obtain trans-substituted olefin compound. The reaction raw material, catalyst and additives is cheap, simple synthesis technology, greatly reduces the cost of synthesizing; mild reaction conditions, high yield, easy industrialization; the reaction of raw materials and catalyst cleaning toxic, small pollution to the environment. The trans-substituted olefin compound and its derivatives as an important fine chemicals, in the medical, agricultural chemicals, perfume and photoelectric and other industries have wide application. (by machine translation)

Manganese-Catalyzed Direct Olefination of Methyl-Substituted Heteroarenes with Primary Alcohols

Herein, we present the first catalytic direct olefination of methyl-substituted heteroarenes with primary alcohols through an acceptorless dehydrogenative coupling. The reaction is catalyzed by a complex of the earth-abundant transition metal manganese that is stabilized by a bench-stable NNN pincer ligand derived from 2-hydrazinylpyridine. The reaction is environmentally benign, producing only hydrogen and water as byproducts. A large number of E-disubstituted olefins were selectively obtained with high efficiency.

Synthesis of (E)-2-Alkenylazaarenes via Dehydrogenative Coupling of (Hetero)aryl-fused 2-Alkylcyclic Amines and Aldehydes with a Cobalt Nanocatalyst

To date, the synthesis of (E)-2-alkenylazaarenes via the condensation of 2-methyl N-heteroarenes with aldehydes or their equivalents has been well demonstrated. However, the direct formation of such a class of useful compounds from extensively distributed 2-alkylcyclic amine motifs remains an unresolved goal. Herein, by employing the nitrogen-silica-doped carbon (Vulcan XC-72R) as the support, we have developed a low-loading cobalt nanocatalyst (Co/N-Si-C). The combination of such a catalyst with p-nitrobenzoic acid and molecular O2 exhibits excellent catalytic performance towards the dehydrogenative coupling of (hetero)aryl-fused 2-alkylcyclic amines with aldehydes to afford the (E)-2-alkenylazaarenes. In the reaction, effective capture of the partially dehydrogenated cyclic amine motifs appears to be the key strategy to address the issue of the chemoselectivity. The developed catalytic transformation proceeds with the merits of broad substrate scope, good functional group tolerance, high atom-efficiency, use of an earth-abundant and reusable cobalt catalyst and molecular O2 as a green oxidant, which offers an important basis for the direct conversion of inert cyclic amine units into the functional frameworks.