4714-21-0

Usage

Uses

Used in Organic Synthesis:
4-Methylstilbene is used as a building block for the synthesis of various organic compounds due to its versatile chemical structure and reactivity.
Used in Pharmaceuticals:
In the pharmaceutical industry, 4-Methylstilbene is utilized as a precursor in the development of new drugs, leveraging its chemical properties to create novel therapeutic agents.
Used in Photophysics and Photochemistry:
4-Methylstilbene is employed as a component in studies and applications related to photophysics and photochemistry, capitalizing on its photochemical properties such as photooxidation and photodimer formation.
Used in Fluorescent Dyes:
This chemical compound is used in the creation of fluorescent dyes, where its photophysical properties contribute to the development of materials with specific light-emitting characteristics.
Used as an Antioxidant:
4-Methylstilbene is studied for its potential use as an antioxidant, which could be beneficial in various applications where protection against oxidative stress is required.

InChI:InChI=1/C15H14/c1-13-7-9-15(10-8-13)12-11-14-5-3-2-4-6-14/h2-12H,1H3

Upstream product

• 99429-99-9 4-methylphenyl cinnamate 
• 20498-63-9 1-(4-methylphenyl)-2-phenylethanol 
• 19019-27-3 phenyl-4-methylphenylbenzaldehyde azine 
• 140-10-3 (E)-3-phenylacrylic acid 
• 106-49-0 p-toluidine 
• 2001-28-7 2-phenyl-1-p-tolyl-ethanone 
• 100-42-5 styrene 
• 60126-95-6 p-tolylazoxy p-tolyl sulphone 
• 10557-67-2 N-nitroso-p-methyl-acetanilide 
• 33604-67-0 (4-methylphenyl)azo 4-methylphenyl sulfone 
• 60126-94-5 phenylazoxy p-tolyl sulphone 
• 106-38-7 para-bromotoluene 
• 624-31-7 4-tolyl iodide 
• 5720-05-8 4-methylphenylboronic acid 

Downstream Products

• 109652-91-7 1-(4-trans-styryl-benzyl)-pyridinium; bromide 
• 1657-45-0 (Z)-4-methylstilbene 
• 14310-20-4 4-methylbibenzyl 
• 102009-55-2 diethyl-(4-trans-styryl-benzyl)-amine 
• 110050-03-8 dipropyl-(4-trans-styryl-benzyl)-amine 
• 10516-47-9 bis-(2-hydroxy-ethyl)-(4-trans-styryl-benzyl)-amine 
• 100461-32-3 meso-4-methylstilbene dibromide 
• 74614-35-0 α-methoxy-4'-methyl-deoxybenzoin oxime 
• 16726-79-7 trans-1-(4-Phenyl-styryl)-4-stryl-benzol 
• 6194-48-5 Phenyl-β-naphthyldivinylbenzene (P-β-NDVβ) 
• 70151-74-5 4-styrylbenzyl bromide 
• 2131-85-3 1-(4-chloro-trans-styryl)-4-trans-styryl-benzene 
• 24601-55-6 ethyl trans-2-(4-methylphenyl)-3-phenylcyclopropanecarboxylate 
• 72301-55-4 2-Fluoro-1-phenyl-2-p-tolyl-ethanol 

Relevant academic research and scientific papers

Simple kinetic method for distinguishing between homogeneous and heterogeneous mechanisms of catalysis, illustrated by the example of "ligand-free" suzuki and heck reactions of aryl iodides and aryl bromides

Using a simple method based on an analysis of the phase trajectories of competing reactions of several substrates, it has been established that the selectivity of catalytically active species in the Suzuki reaction of aryl bromides depends on the nature of the catalyst precursor. This indicates that there is a considerable contribution from heterogeneous catalysis. At the same time, in the reaction involving aryl iodides, when the catalyst concentration in the solution is much higher, the selectivity of the catalyst is precursor-independent, suggesting that homogeneous catalysis is dominant. In the Heck reaction of both aryl bromides and aryl iodides, pure homogeneous catalysis takes place. Pleiades Publishing, Ltd., 2012.

Charge-tagged acetate ligands as mass spectrometry probes for metal complexes investigations: Applications in suzuki and heck phosphine-free reactions

An acetate anion bearing an imidazolium cation as its charge tag was reacted with M(OAc)2 complexes (where M = Ni, Cu, and Pd; in situ reaction) to form members of a new class of charge-tagged metal complexes. The formation of these unprecedented precatalysts with potential for cross-coupling reactions was confirmed by electrospray ionization (and tandem) mass spectrometry. The catalytic performance of the palladium complex was tested in Heck and Suzuki cross-coupling reactions, often with superior activity and yields as compared with Pd(OAc)2.

Phosphine-Functionalized Chitosan Microparticles as Support Materials for Palladium Nanoparticles in Heck Reactions

Herein, we investigated the activation and stabilization of Pd nanoparticles using microparticles of chitosan-functionalized with phosphine moieties. The catalytic activity of the prepared material was assessed in a series of Heck reactions, which demonst

Pd-Catalyzed desulfitative arylation of olefins by: N -methoxysulfonamide

A novel Pd-catalyzed protocol for the desulfitative Heck-type reaction of N-methoxy aryl sulfonamides with alkenes was reported. The cross-coupling reaction was performed successfully with a variety of olefins to obtain aryl alkenes. Different substituents on the aromatic ring of N-methoxysulfonamides were also found to be compatible with the reaction conditions. Expectedly, the reaction proceeds through CuCl2-promoted generation of the nitrogen radical and subsequent desulfonylation under thermal conditions to afford the aryl radical for the Pd-catalyzed coupling reaction. N-Methoxysulfonamide was further exploited for the synthesis of symmetrical biaryls in the presence of CuCl2. This journal is

Palladium Nanoparticles Supported on Cellulosic Paper as Multifunctional Catalyst for Coupling and Hydrogenation Reactions

Hallmark of a successful catalyst is its high efficiency, economic aspects, operational simplicity, extensive reusability, higher environment friendliness, and potential use in multiple industrial applications. Herein, a facile protocol involving a cataly

Heterobimetallic Pd/Mn and Pd/Co complexes as efficient and stereoselective catalysts for sequential Cu-free Sonogashira coupling–alkyne semi-hydrogenation reactions

A series of heterobimetallic PdII/MII complexes (MII = Mn, Co) were synthesised and tested as precatalysts for sequential Sonogashira coupling–alkyne semi-hydrogenation reactions to form Z-aryl alkenes. The carbometalated heterobimetallic PdII/CoII complex CoPdL3′ demonstrated an apparent cooperative effect compared to the corresponding monometallic counterparts. This compound was identified as a potent single-molecule catalyst for the one-pot Cu-free Sonogashira coupling of aryl bromides with terminal alkynes followed by chemo- and stereoselective semi-hydrogenation of the alkyne intermediate using NH3·BH3 as a hydrogen source. Furthermore, different aromatic substrates have been tested to show the generality of the reaction for the synthesis of Z-alkenes, including biologically active combretastatin A-4. In addition, the homogeneous nature of the catalytically active species was demonstrated.

Synthesis of new adamantyl-imine palladium(II) complexes and their application in Mizoroki-Heck and Suzuki-Miyaura C[sbnd]C cross-coupling reactions

Improving carbon–carbon cross-coupling reactions is an ongoing process and finding the most versatile and stable catalyst precursors has been of great interest. Ligand design has been proven to be important since it is responsible for providing electron density and steric saturation around the metal centre, thus contributing towards the stereo-electronic properties. The adamantyl moiety has been used to generate highly bulky and electron-rich ligands for application in palladium-catalysed cross-coupling reactions. Accordingly, we have prepared some Schiff-base adamantyl ligands (L1-L3) and complexed them with [PdCl2(MeCN)2] to afford the (pre)catalysts C1-C3, which were successfully applied in Mizoroki-Heck and Suzuki-Miyaura carbon–carbon cross-coupling reactions. The cross-coupling reaction products were obtained in good yields using 0.5 mol % Pd catalyst loading. C2 and C3 showed remarkable activity in the Mizoroki-Heck coupling reactions involving substrates with substituents on the olefin and aryl halide (including 4-Cl, 4-CH3, -CO2Me and -CO2Et). We also, observed that the Suzuki-Miyaura cross-coupling system was active towards challenging activated and deactivated aryl chlorides, with to up 70% conversions recorded. The mercury poisoning tests conducted revealed that the catalysts act as homogenous molecular active species in the Mizoroki-Heck reactions and act as both homogenous and heterogeneous catalysts in the Suzuki-Miyaura cross-coupling reactions.

Recyclable heterogeneous iron supported on imidazolium ionic liquid catalysed palladium and copper-free Heck reaction

A natural friendly iron-immobilized on imidazolium supported ionic liquid [Gmim]Cl-Fe (III) was effectively evaluated as a heterogeneous catalyst for Mizoroki-Heck reaction with good to excellent yield under solvent free condition. [Gmim]Cl-Fe (III) showed good activities that were comparable to that of palladium catalysts. Furthermore, this phosphine, copper and palladium- free catalyst was simply recovered from the reaction mixture and recycled seven times.

Palladium Complexes with Phenoxy- And Amidate-Functionalized N-Heterocyclic Carbene Ligands Based on 3-Phenylimidazo[1,5- a]pyridine: Synthesis and Catalytic Application in Mizoroki-Heck Coupling Reactions with Ortho-Substituted Aryl Chlorides

Mononuclear and tetranuclear palladium complexes with functionalized "abnormal"N-heterocyclic carbene (aNHC) ligands based on 3-phenylimidazo[1,5-a]pyridine were synthesized. All of the new complexes were structurally characterized by single-crystal X-ray diffraction studies. The new complexes were applied in the Mizoroki-Heck coupling reaction of aryl chlorides with alkenes in neat n-tetrabutylammonium bromide (TBAB). The mononuclear palladium complex with a tridentate phenoxy- and amidate-functionalized aNHC ligand displayed activity superior to that of the palladium complex with a bidentate amidate-functionalized aNHC ligand. The new tetranuclear complex with the tridentate ligand displayed the best activities, capable of the activation of deactivated aryl chlorides as substrates with a low Pd atom loading. Even challenging sterically demanding ortho-substituted aryl chlorides were successfully utilized as substrates. The studies revealed that the robustness of the catalyst precursor is crucial in delivering high catalytic activities. Also, the promising use of tetranuclear palladium complexes with functionalized aNHC ligands as the catalyst precursors in the Mizoroki-Heck coupling reaction in neat TBAB was demonstrated.

N-Heterocyclic carbene palladium (II)-pyridine (NHC-Pd (II)-Py) complex catalyzed heck reactions

A mild, efficient, and practical catalytic system for the synthesis of highly privileged stilbene pharmacophores is reported. This system uses N-heterocyclic carbene palladium (II) Pyridine (NHC-Pd (II)-Py) complex to catalyze the formation of carbon-carbon bonds between olefin derivatives and various bromide. This simple, gentle and user-friendly method can offer a variety of stilbene products in excellent yields under solvent-free condition. And its scale-up reaction has excellent yield and this system can be applied to industrial fields. The utility of this method is highlighted by its universality and modular synthesis of a series of bioactive molecules or important medical intermediates.