5043-91-4

Usage

SMILES code

OC(=O)C=CC1=C(C=CC(C2=CC=C(Cl)C=C2)=C1)C(=O)C

Molecular weight

252.73 g/mol

Functional groups

Chlorine atom, methoxy group, phenyl ring, vinyl group

Structure

Contains two phenyl rings connected by a vinyl group, with a chlorine atom and a methoxy group attached to one of the phenyl rings

Physical state

Likely a solid at room temperature, based on its molecular weight and structure

Applications

Used in organic synthesis and research as a starting material for the production of various pharmaceuticals, agrochemicals, and dyes; used as a building block for the synthesis of various organic compounds; has applications in the field of medicinal chemistry

Environmental considerations

Potential environmental pollutant; should be handled and disposed of with care to minimize its impact on the environment

Hazards

Not specified in the provided material, but may include toxicity, flammability, or reactivity with other substances, depending on its specific properties and handling conditions.

Upstream product

• 104-87-0 4-methyl-benzaldehyde 
• 135705-51-0 p-chlorobenzyldibutyltelluronium bromide 
• 51044-12-3 (4-chlorobenzyl)triphenylphosphonium bromide 
• 123-11-5 4-methoxy-benzaldehyde 
• 622-95-7 4-chlorobenzyl bromide 
• 824-94-2 p-methoxybenzyl chloride 
• 104-88-1 4-chlorobenzaldehyde 
• 105336-81-0 4(C₅H₅)^(1-)*2Zr⁽⁴⁺⁾*2(NNCHC₆H₄OCH₃)^(2-)=((C₅H₅)2ZrNNCHC₆H₄OCH₃)2 
• 1073-67-2 4-vinylbenzyl chloride 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 696-62-8 para-iodoanisole 
• 637-69-4 4-Methoxystyrene 
• 106-39-8 bromochlorobenzene 
• 1145-93-3 diethyl 4-methoxybenzylphosphonate 

Downstream Products

• 2131-84-2 1-methoxy-4-(4-styrylstyryl)benzene 
• 1608492-52-9 (2R,3S,4R,5S)-3,4-bis(4-chlorophenyl)2,5-bis(4-methoxyphenyl)tetrahydrofuran 
• 5043-91-4 (E)-4-chloro-4'-methoxystilbene 
• 1333128-06-5 5-[4-[(E)-2-(4-methoxyphenyl)vinyl]phenyl]-1,2-dimethylimidazole 
• 1333128-07-6 3-[4-[2-(4-methoxyphenyl)ethenyl]phenyl]imidazo[1,2-a]pyridine 
• 18951-46-7 (E)-4-<2-(4-chlorophenyl)ethenyl>phenol 
• 1588534-24-0 C₂₈H₂₀Cl₂O₂ 
• 54945-17-4 1-(4-chlorophenyl)-2-(4-methoxyphenyl)-ethane-1,2-dione 
• 10547-60-1 4-chloro-4'-methoxybenzophenone 

Relevant academic research and scientific papers

Synthesis, crystal structure, and catalytic activity of bridged-bis(N-heterocyclic carbene) palladium(II) complexes in selective Mizoroki-Heck cross-coupling reactions

A series of three 1,3-propanediyl bridged bis(N-heterocyclic carbene)palladium(II) complexes (Pd-BNH1, Pd-BNH2, and Pd-BNH3), with + I effect order of the N-substituents of the ligand (isopropyl > benzyl > methoxyphenyl), was the subject of a spectroscopic, structural, computational and catalytic investigation. The bis(NHC)PdBr2 complexes were evaluated in Mizoroki-Heck coupling reactions of aryl bromides with styrene or acrylate derivatives and showed high catalytic efficiency to produce diarylethenes and cinnamic acid derivatives. The X-ray structure of the most active palladium complex Pd-BNH3 shows that the Pd(II) center is bonded to the two carbon atoms of the bis(N-heterocyclic carbene) and two bromide ligands in cis position, resulting in a distorted square planar geometry. The NMR data of Pd-BNH3 are consistent with a single chair-boat rigid conformer in solution with no dynamic behavior of the 8-membered ring palladacycle in the temperature range 25–120 °C. The catalytic activities of three Pd-bridged bis(NHC) complexes in the Mizoroki-Heck cross-coupling reactions were not found to have a direct correlation with +I effect order of the N-substituents of the ligand. However, a direct correlation was found between the DFT calculated absolute softness of the three complexes with their respective catalytic activity. The highest calculated softness, in the case of Pd-BNH3, is expected to favor the coordination steps of both the soft aryl bromides and alkenes in the Heck catalytic cycle.

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.

Transition-Metal-Free Matsuda-Heck Type Cross-Coupling and Mechanistic Evidence for a Radical Mechanism

The Matsuda-Heck reaction, usually performed with palladium catalysts, can be carried out under transition-metal-free conditions in the presence of a KOtBu/DMF couple. This system allows the selective and direct synthesis of stilbenes from aryldiazonium salts under mild temperature (20 °C). Mechanistic studies suggest a radical pathway in which the DMF acts as the initiator of the overall process.

Dual ligand-promoted palladium-catalyzed nondirected C-H alkenylation of aryl ethers

Direct C-H functionalization of aryl ethers remains challenging owing to their low reactivity and selectivity. Herein, a novel strategy for nondirected C-H alkenylation of aryl ethers promoted by a dual ligand catalyst was demonstrated. This catalytic system readily achieved the highly efficient alkenylation of alkyl aryl ethers (anisole, phenetole, n-propyl phenyl ether, n-butyl phenyl ether and benzyl phenyl ether), cyclic aryl ethers (1,4-benzodioxan, 2,3-dihydrobenzofuran, dibenzofuran), and diphenyl oxides. Moreover, the proposed methodology was successfully employed for the late-stage modification of complex drugs containing the aryl ether motif. Interestingly, the compounds developed herein displayed fluorescent properties, which would facilitate their biological applications.

Diarylethene synthesis method without transition metal catalysis

The invention discloses a diarylethene synthesis method without transition metal catalysis. The method comprises the following steps: a cinnamic acid derivative and aryl trifluoroborate are subjectedto a decarboxylation coupling reaction in a solvent under the action of an oxidizing agent, postprocessing is performed after the reaction, and diarylethene is obtained. K2S2O8 is adopted to promote acatalytic system in the synthetic method, and a free radical coupling reaction can be performed directly under the condition that no ligand, transition metal or alkali is added. The method has widersubstrate range and higher yield; the method is simple to operate, reaction conditions are mild, and large-scale application is facilitated.

Preparation method of palladium catalyzed 1,2-trans diaryl alkene

The invention discloses a preparation method of palladium catalyzed 1,2-trans diaryl alkene. The method comprises the following steps that under the effects of catalysts, cocatalysts and alkali, arylacrylic acid and aromatic esters p-toluene sulfonate take decarboxylation coupling reaction in an organic solvent; after the reaction is finished, the 1,2-trans diaryl alkene is obtained through posttreatment. The method has the advantages that through C-O bond fracture, the operation is simple; a stable palladium catalyst with low cost is used; the substrate applicability is high; the harsh reaction conditions and the addition of strong alkali are not needed; the trans 1,2-diaryl alkene can be generated at high selectivity.

Palladium nanoparticles immobilized on Schiff base-functionalized mesoporous silica as a highly efficient and magnetically recoverable nanocatalyst for Heck coupling reaction

A new magnetically recoverable nanocatalyst was prepared by functionalization of mesoporous silica (SBA-15) with a Schiff base ligand, and then immobilization of palladium nanoparticles on it using a simple procedure. This heterogeneous catalyst was fully characterized using appropriate analyses and its catalytic efficiency was investigated in Heck reaction using iodo-, bromo- and chlorobenzene derivatives and styrene, with the aim of synthesizing stilbene derivatives, a class of compounds with a variety of pharmacological properties. Some of the characteristics of this nanocatalyst include good dispersion of palladium nanoparticles on the SBA-15 support, easy separation, catalyses the production of stilbene derivatives in a short time with excellent yields even for bromo- and chlorobenzene, and preservation of its catalytic activity after eight reaction cycles.

Facile synthesis of a recyclable Pd-rGO/CNT/CaFe2O4 nanocomposite with high multifunctional photocatalytic activity under visible light irradiation

We report a facile method to synthesize a magnetically separable Pd-rGO/CNT/CaFe2O4 photocatalyst. The incorporation of CNTs into rGO can form a conductive network structure to bridge the gaps between rGO sheets. This conductive netw

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.

Synthesis and characterization of a new zwitterionic palladium complex as an environmentally friendly catalyst for the Heck-Mizoroki coupling reaction in GVL

A new zwitterionic Palladium (II) complex has been synthesized by the one-pot mixing of Pd(OAc)2, 2-aminophenol and (3-formyl-4-hydroxy-5-methylbenzyl) triphenylphosphonium chloride, in refluxing ethanol. The metal complex formed was characterized by 1H NMR, 13C NMR, 31P NMR and X-ray crystallographic technique and its efficiency tested as a homogeneous pre-catalyst in Heck-Mizoroki cross coupling reaction using γ-Valerolactone (GVL) as a biomass-derived green medium. All the products were obtained in good to excellent yields.