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Usage

Uses

Used in Pharmaceutical Industry:
(E)-1-(2-Bromovinyl)-2-methylbenzene is used as a starting material for the synthesis of various pharmaceutical compounds. Its unique structure allows for the creation of a wide range of medicinal agents, contributing to the development of new drugs and therapies.
Used in Agrochemical Industry:
In the agrochemical sector, (E)-1-(2-Bromovinyl)-2-methylbenzene is employed as a precursor for the production of different agrochemicals. Its versatility in synthesis enables the creation of compounds that can be used in the development of pesticides, herbicides, and other agricultural products to enhance crop protection and yield.
Used in Organic Synthesis:
(E)-1-(2-Bromovinyl)-2-methylbenzene is utilized as a key intermediate in organic synthesis, allowing for the formation of a diverse array of organic compounds. Its reactivity and structural features make it a valuable component in the synthesis of specialty chemicals, materials, and other complex molecules for various applications across different industries.

Upstream product

• 2373-76-4 2-methylcinnamic acid 
• 104464-03-1 1,1-dibromo-2-(2-methylphenyl)ethene 
• 529-20-4 2-methylphenyl aldehyde 

Downstream Products

• 832-69-9 1-methylphenanthrene 
• 67535-55-1 9-(2-methylbenzylidene)-9H-fluorene 
• 889869-30-1 trans-1-(2-bromovinyl)-2-methylbenzene 
• 1313709-36-2 trans-(2-methyl)-1-phenylthiostyrene 

Relevant academic research and scientific papers

Selective Rhodium-Catalyzed Hydroformylation of Terminal Arylalkynes and Conjugated Enynes to (Poly)enals Enabled by a π-Acceptor Biphosphoramidite Ligand

The hydroformylation of terminal arylalkynes and enynes offers a straightforward synthetic route to the valuable (poly)enals. However, the hydroformylation of terminal alkynes has remained a long-standing challenge. Herein, an efficient and selective Rh-catalyzed hydroformylation of terminal arylalkynes and conjugated enynes has been achieved by using a new stable biphosphoramidite ligand with strong π-acceptor capacity, which affords various important E-(poly)enals in good yields with excellent chemo- and regioselectivity at low temperatures and low syngas pressures.

A Simplified Protocol for the Stereospecific Nickel-Catalyzed C-S Vinylation Using NiX 2 Salts and Alkyl Phosphites

A Ni-catalyzed C-S cross-coupling using only NiI 2 (0.5-2.5 molpercent) and P(O i Pr) 3 (2.0-10.0 molpercent) is reported. Using an air-stable Ni(II) precatalyst, and a cheap and commercially available ligand, a scalable and robust method was developed to cross-couple various thiophenols and styryl bromides, including some sterically encumbered thiols, an α-bromocinnamaldehyde as well as a thiolation-cyclization.

Construction of Phenanthrenes and Chrysenes from β-Bromovinylarenes via Aryne Diels-Alder Reaction/Aromatization

A highly efficient transition-metal-free general method for the synthesis of polycyclic aromatic hydrocarbons like phenanthrenes and chrysenes (and tetraphene) from β-bromovinylarenes and arynes has been developed. The reactions proceed via an aryne Diels-Alder (ADA) reaction, followed by a facile aromatization. This is the first report on direct construction of chrysenes (and tetraphene) using the ADA approach. Unlike the literature method which is limited to only 9/10-substituted derivatives, this method gives access to a wide variety of functionalized phenanthrenes.

Metal-Mediated Debromination of gem-Dibromoalkenes under Mild Conditions

We describe the facile and efficient metal-promoted reduction of C-Br bonds of gem-dibromides. When the reaction is mediated by indium, the corresponding vinyl bromides are obtained in good yields and high E-stereoselectivities. Alternatively, when the reduction is mediated by samarium diiodide, vinyl bromides are obtained in moderate yields and good Z-selectivities.

Ultrasonically Assisted Decarboxylative Bromination of α,β-Unsaturated Carboxylic Acids under Vilsmeier-Haack Conditions

An efficient method for decarboxylative bromination of cinnamic acids (α,β-unsaturated carboxylic acids or 3-arylpropenoic acids) was achieved under relatively mild conditions using Vilsmeier-Haack reagent and KBr in acetonitrile media. Vilsmeier-Haack reagent is prepared by using 1:1 ratio of oxychloride (SOCl2 or POCl3) and DMF under chilled condition. Ultrasonically assisted reactions underwent smoothly with highly significant rate enhancements and afforded bromostyrenes as products in very good yields even though the reactions were too sluggish.

Palladium(0)-catalyzed cross-coupling of 1,1-diboronates with vinyl bromides and 1,1-dibromoalkenes

Palladium-catalyzed cross-coupling reactions of 1,1-diboronates with vinyl bromides and dibromoalkenes were found to afford 1,4-dienes and allenes, respectively. These reactions utilize the high reactivities of both 1,1-diboronates and allylboron intermediates generated in the initial coupling.