62856-31-9

Usage

Uses

Used in Chemical Synthesis:
Benzene, 1-bromo-4-[2-(4-methylphenyl)ethenyl]is used as a reactant in the preparation of 4-n-alkyl-4''-cyanotolanes. This application is significant in the synthesis of various organic compounds and pharmaceuticals, as 4-n-alkyl-4''-cyanotolanes serve as key intermediates in the production of a wide range of chemical products.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Benzene, 1-bromo-4-[2-(4-methylphenyl)ethenyl]is utilized as a building block for the synthesis of various drug molecules. Its unique structure and reactivity make it a valuable component in the development of new medications and therapeutic agents.
Used in Research and Development:
Benzene, 1-bromo-4-[2-(4-methylphenyl)ethenyl]is also employed in research and development settings, where it is used to study the properties and behavior of organic compounds. Its reactivity and structural features make it an interesting subject for scientific investigations, contributing to the advancement of knowledge in organic chemistry and related fields.

Upstream product

• 2039-82-9 1-bromo-4-ethenyl-benzene 
• 106-38-7 para-bromotoluene 
• 104-87-0 4-methyl-benzaldehyde 
• 51044-13-4 4-bromobenzyl triphenylphosphonium bromide 
• 1530-37-6 (4-methylbenzyl)triphenylphosphonium chloride 
• 1122-91-4 4-bromo-benzaldehyde 
• 673-40-5 4-bromobenzenediazonium tetrafluoroborate 
• 73839-45-9 (E)-trimethyl[2-(4-methylphenyl)ethenyl]silane 
• 766-96-1 4-bromo-1-ethynylbenzene 
• 6293-68-1 bis(4-methylphenyl)iodonium bromide 
• 589-87-7 1,4-bromoiodobenzene 
• 149777-84-4 4,4,5,5-tetramethyl-2-[(E)-2-p-tolylethenyl]-1,3,2-dioxaborolane 
• 624-31-7 4-tolyl iodide 
• 104-82-5 4-Methylbenzyl chloride 

Downstream Products

• 1395063-64-5 (Z)-4-[2-(4-methylphenyl)vinyl]biphenyl 
• 2131-83-1 1-(4-methyl-trans-styryl)-4-trans-styrylbenzene 
• 32092-95-8 (E)-2-(p-bromophenyl)-3-p-tolylcyclopropanecarboxylic acid 
• 143959-01-7 ethyl N-<(E)-2-(p-bromophenyl)-3-p-tolylcyclopropyl>carbamate 
• 143959-10-8 ethyl N-nitroso-N-<(E)-2-(p-bromophenyl)-3-p-tolylcyclopropyl>carbamate 
• 1422172-84-6 (E)-4,4,5,5-tetramethyl-2-(4-(4-methylstyryl)phenyl)-1,3,2-dioxaborolane 

Relevant academic research and scientific papers

N-Methylphenothiazine S-Oxide Enabled Oxidative C(sp2)–C(sp2) Coupling of Boronic Acids with Organolithiums via Phenothiaziniums

Herein, we report the development of a transition-metal-free oxidative C(sp2)–C(sp2) coupling of readily available boronic acids and organolithiums via phenothiazinium ions. Various biaryl, styrene, and diene derivatives were obtained using this reaction system. The key to this process is N-methylphenothiazine S-oxide (PTZSO), which allows efficient conversion of boronic acids to phenothiazinium ions. The mechanism of phenothiazinium formation using PTZSO was investigated using theoretical calculations and experiments, which provided insight into the unique reactivity of PTZSO.

E, Z -Selectivity in the reductive cross-coupling of two benzaldehydes to stilbenes under substrate control

Unsymmetrical E- and Z-stilbenes can be synthesized from two differently substituted benzaldehydes in a MesP(TMS)Li-promoted reductive coupling sequence. Depending on the order of addition of the two coupling partners, the same olefin can be produced in either E- or Z-enriched form under identical reaction conditions. A systematic study of the correlation between the stereochemical outcome of the reaction and the substitution pattern at the two aldehydes is presented. The results can be used as guidelines to predict the product stereochemistry. This journal is

Novel Carbazole-Based N-Heterocyclic Carbene Ligands to Access Synthetically Relevant Stilbenes in Pd-Catalyzed Coupling Processes

A series of new carbazole-based N-heterocyclic carbene (NHC) ligands have been synthesized in a simple and facile synthetic route and subsequently used in a Pd/carbazole-based NHC catalytic system, which was found to be effective in catalyzing Heck reactions to provide substituted stilbene derivatives in good yields. Several bioactive stilbenes, including pterostilbene, pinosylvin, trimethoxy resveratrol, and resveratrol, were synthesized in good yields, and a 10 mmol scale-up was also performed for trimethoxy resveratrol. The synthetic application was also extended by performing a double-tandem chemoselective Heck reaction followed by Miyaura borylation in a one-pot procedure to give single-step access to synthetically useful stilbenyl boronate esters. Similarly, a unique triple-tandem protocol of a chemoselective Heck reaction/Miyaura borylation/Suzuki–Miyaura coupling reaction sequence was performed for the one-pot modification of biologically relevant molecules.

Ligand-controlled iridium-catalyzed semihydrogenation of alkynes with ethanol: highly stereoselective synthesis of E- and Z-alkenes

A ligand-controlled iridium-catalyzed semihydrogenation of alkynes to E- and Z-alkenes with ethanol was developed. Effective selectivity control was achieved by ligand regulation. The use of 1,2-bis(diphenylphosphino)ethane (DPPE) and 1,5-cyclooctadiene (COD) was critical for the stereoselective semihydrogenation of alkynes. The general applicability of this procedure was highlighted by the synthesis of more than 40 alkenes, with good stereoselectivities. The value of our approach in practical applications was investigated by studying the effects of pinosylvin and 4,4′-dihydroxystilbene (DHS) on zebrafish as a vertebrate model.

Method for catalytic-selectively synthesizing Z- and E-alkene through alcohol supply hydrogen iridium controlled by ligand

The invention discloses a method for catalytic-selectively synthesizing Z- and E-alkene through alcohol supply hydrogen iridium controlled by a ligand. The method comprises the following steps: usinga disubstituted acetylene compound as a starting raw mat

Method of photo-induced catalytic selective synthesis of Z- and E-olefins

The invention discloses a method of photo-induced catalytic selective synthesis of Z- and E-olefins. According to the method, a disubstituted acetylene compound is used as a starting raw material, a cheap acid is used as a hydrogen source, a phosphine is

Photo-induced catalytic method for selectively synthesizing cis olefin and trans olefin by using alcohol as hydrogen source

The invention discloses a photo-induced catalytic method for selectively synthesizing a cis olefin and a trans olefin by using alcohol as a hydrogen source. According to the method, a di-substituted acetylene compound is used as an initial raw material, t

Piperidine-appended imidazolium ionic liquid as task-specific basic-IL for Suzuki and Heck reactions and for tandem Wittig-Suzuki, Wittig-Heck, Horner-Emmons-Suzuki, and Horner-Emmons-Heck protocols

Facile, high yielding, one-pot methods for the synthesis of a library of diversely substituted bi-aryls, diarylethenes, and aryl-enoates, via Suzuki and Heck reactions, and by sequential Wittig-Suzuki, Wittig-Heck, Horner-Emmons-Suzuki, and Horner-Emmons-Heck reactions are reported. The reactions employ piperidine-appended imidazolium ionic liquid [PAIM][NTf2] as a task-specific basic-IL, butyl-methyl-imidazolium ionic liquid [BMIM][X] (X?=?PF6, BF4) as solvent, and catalytic amounts of Pd(OAc)2 with no other additives. Wittig and Horner-Emmons reactions are effected by reacting substituted benzaldehydes with 4-bromobenzyl-PPh3 (or bromomethyl-PPh3) phosphonium salts, or diethylphosphonate with bromobenzaldehydes respectively, to form the corresponding ethenes. Subsequent cross-coupling reactions are accomplished by addition of aryl-boronic acid or phenyl-ethenes along with Pd(OAc)2 to bring about the aforementioned hyphenated transformations. The feasibility to perform double-olefination via Wittig and Horner-Emmons reactions with dialdehydes to form highly conjugated bis-styryl and bis-enoate compounds is also shown. The [BMIM][X] solvent is recycled and reused.

Synthesis of stilbene derivatives via visible-light-induced cross-coupling of aryl diazonium salts with nitroalkenes using-NO2 as a leaving group

The straightforward visible-light-induced synthesis of stilbene compounds via the cross-coupling of nitroalkenes and diazonium tetrafluoroborates under transition-metal-free conditions is described. The protocol uses green LEDs as light sources and eosin Y as an organophotoredox catalyst. Broad substrate scope and exclusive selectivity for the (E)-configuration of stilbenes are observed. This protocol proceeds via a radical pathway, with nitroalkenes serving as the radical acceptor, and the nitro group is cleaved during the process.

Iminophosphine palladium(II) complexes: Synthesis, characterization, and application in Heck cross-coupling reaction of aryl bromides

Palladium(II) complexes containing phosphorus and nitrogen donor atoms (iminophosphine), dichlorido{N-[2-(diphenylphosphino)benzylidene]-2- trifluoromethylaniline}palladium(II) 1, dichlorido{N-[2-(diphenylphosphino) benzylidene]-3-trifluoromethylaniline}palladium(II) 2, dichlorido{N-[2- (diphenylphosphino)benzylidene]-2-methylaniline}palladium(II) 3, dichlorido{N-[2-(diphenylphosphino)benzylidene]-3-methylaniline}palladium(II) 4 have been successfully synthesized and fully characterized by FT-IR and NMR (1H, 31P, 19F, and 13C) spectroscopy techniques. These complexes were first step tested in the reaction of bromobenzene and styrene to determine the optimal coupling reaction conditions and then successfully applied as catalysts for Heck cross-coupling reactions of activated and deactivated aryl bromides with styrene derivatives and several acrylates. Copyright