125142-06-5

Usage

Uses

Used in Organic Synthesis:
(Z)-2-(2-Bromoethenyl)pyridine is used as a key intermediate in organic synthesis for the creation of a wide range of chemical products. Its unique structure allows for further functionalization and modification, making it a valuable component in the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (Z)-2-(2-Bromoethenyl)pyridine is used as a building block for the development of new drugs. Its structural properties enable the creation of novel pharmaceutical compounds with potential therapeutic applications.
Used in Agrochemicals:
(Z)-2-(2-Bromoethenyl)pyridine is also utilized in the agrochemical sector, where it serves as a starting material for the synthesis of various agrochemical products, such as pesticides and herbicides.
Used in Dye Production:
(Z)-2-(2-Bromoethenyl)pyridine is used as a precursor in the production of dyes, thanks to its ability to form colored compounds when reacted with other chemicals.
Used in Material Science:
(Z)-2-(2-Bromoethenyl)pyridine has potential applications in material science, where it can be used to develop new materials with specific properties, such as conductivity or magnetism.
Used in the Synthesis of Functionalized Pyridine Derivatives:
As a valuable starting material, (Z)-2-(2-Bromoethenyl)pyridine is employed in the synthesis of various functionalized pyridine derivatives. These derivatives exhibit diverse properties and find applications in different fields, including pharmaceuticals, agrochemicals, and material science.

Upstream product

• 1121-60-4 pyridine-2-carbaldehyde 
• 1034-49-7 (bromomethyl)triphenyl phosphonium bromide 
• 109-04-6 2-bromo-pyridine 
• 1945-84-2 2-ethynylpyridine 
• 86521-05-3 2-(trimethylsilylethynyl)pyridine 
• 182815-94-7 2-(2,2-dibromovinyl)-pyridine 

Relevant academic research and scientific papers

Regio- and stereoselective synthesis of bromoalkenes by homolytic hydrobromination of alkynes with hydrogen bromide

Homolytic hydrobromination of terminal and internal alkynes with a commercially available solution of hydrogen bromide in acetic acid has been investigated for regio- and stereoselective synthesis of bromoalkenes. Under an aerobic atmosphere at room temperature, the reaction of ethynylarenes with a small excess of HBr efficiently gave (2-bromoethenyl)arenes with good to high E-selectivity. (Alk-1-ynyl)arenes, or internal alkynes bearing both phenyl and alkyl groups at the sp-carbons also underwent the air-initiated hydrobromination to exhibit high Z-selectivity under kinetic conditions using a half equivalent of HBr.

The hydrodebromination of 1,1-dibromoalkenes via visible light catalysis

Vinyl bromides are versatile synthetic intermediates and widely applied in organic synthesis and pharmaceuticals. Herein, a hydrodebromination reaction of 1,1-dibromoalkenes was established via visible light catalysis. A variety of structurally different vinyl bromides were obtained in moderate to excellent yields.

Nickel(II)-magnesium-catalyzed cross-coupling of 1,1-dibromo-1-alkenes with diphenylphosphine oxide: One-pot synthesis of (E)-1-alkenylphosphine oxides or bisphosphine oxides

A novel nickel(II)-magnesium-mediated cross-coupling of diphenylphosphine oxide with a variety of 1,1-dibromo-1-alkenes has been developed, which provides a powerful and general methodology for the stereoselective synthesis of various (E)-1-alkenylphosphine oxides or bisphosphine oxides, with operational simplicity of the procedure, good to high yields and broad substrate applicability. Mechanistic studies reveal that the reaction might involve a Hirao reduction, cross-coupling and Michael addition. Copyright

Method for the synthesis of 3-substituted indolizine and benzoindolizine compounds

A method of making a compound of Formula I: comprises reacting a compound of Formula II with a compound such as R1OH or R1SH, to produce said compound of Formula I. Compounds of Formula I are useful, among other things, as dyes, spectral sensitizers, glycosidase inhibitors, and as antibacterial, antiviral, and anti-inflammatory agents.

Direct synthesis of monofunctionalized indolizine derivatives bearing alkoxymethyl substituents at C-3 and their benzofused analogues

(Chemical Equation Presented) Treatment of (Z)-2-pyridine and quinoline silylated vinylacetylenes at reflux with several alcohols in the presence of a suitable inorganic base (KOH, K2CO3, CsF, or KF) serendipitously gave 3-alkoxylmet

Practical synthesis of (Z)-polyaromatic and heteroaromatic vinylacetylenes

(Chemical Equation Presented) Two synthetic routes to several (Z)-polyaromatic and heteroaromatic substituted vinylacetylenes are described. The nature of aryl- or heteroaryl-substituted carboxaldehyde used as starting material dictated the choice of Wittig salt employed. A very attractive way to construct polyaromatic and pyridine-containing enynes is the reaction of polyaromatic and pyridine-containing aldehydes with bromomethyltriphenylphosphonium bromide in the presence of potassium tert-butoxide followed by a Sonogashira desilylation procedure (method B).

Stereoselective hydrogenolysis of 1,1-dibromo-1-alkenes and stereospecific synthesis of conjugated (Z)-alkenyl compounds

The Pd-catalyzed hydrogenolysis of 1,1-dibromoalkenes with Bu3SnH occurs at room temperature stereoselectively to give (Z)-1-bromo-1-alkenes. We sought to determine the optimal reaction conditions and illustrate the scope of this method with 32 dibromoalkenes including alkenyl- and alkynyl- conjugated 1,1-dibromo-1-alkenes 7a-h and 2,2-disubstituted 1,1-dibromo-1- alkenes 9af. Triphenylphosphine was the best ligand for the Pd-catalyzed hydrogenolysis. A wide range of solvents can be used for this reaction excluding EtOH, AcOH, and CHCl3. However, the reaction proceeds even in these solvents with the addition of a cosolvent or radical scavenger. The reaction of 1,1-diiodo-1-alkene (3) gave a mixture of (Z)-1-iodo-1-alkene (4), (Z)-1-tributylstannyl-1-alkene (5), and a terminal alkene 6, while that of 1,1-dichloroalkene did not occur. This selectivity can be explained by the stereoselective insertion of Pd(0) to a trans bromine-alkenyl carbon bond, successive transmetalation with Bu3SnH, and reductive elimination. The Suzuki and Sonogashira couplings of the resulting (Z)-1-bromo-1-alkenes with alkenyl(dialkoxy)borane and terminal alkyne occurred to give conjugated polyenes and enynes stereospecifically. The Pd-catalyzed hydrogenolysis of 1,1-dibromo-1-alkene and successive cross-coupling can be carried out either in a stepwise manner or in one-pot under the same Pd catalysis. These two processes should be useful for the synthesis of geometrically pure polyene and enyne with a Z-alkenyl unit.

A general and convenient synthetic method of geometrically pure (Z)-1-bromo-1-alkenes

Palladium catalyzed hydrogenolysis of 1,1-dibromo-1-alkenes by tributyltin hydride proceeds smoothly to give (Z)-1-bromo-1-alkenes with excellent stereoselectivity in good yields. Dibromomethylenation of aldehydes by a combination of CBr4 and P