1472-68-0

Usage

Uses

Used in Dye and Fluorescent Chemical Production:
4-Methoxy-4'-nitrostilbene is used as a key intermediate in the production of dyes and fluorescent chemicals, leveraging its distinctive optical properties to enhance the performance and characteristics of these products.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, 4-Methoxy-4'-nitrostilbene serves as a potential intermediate for the synthesis of various drugs, contributing to the development of new medications with improved therapeutic effects.
Used in Agrochemical Synthesis:
Similarly, in the agrochemical sector, 4-Methoxy-4'-nitrostilbene is utilized as an intermediate in the synthesis of different agrochemicals, potentially leading to the creation of more effective and environmentally friendly products for agricultural applications.
Safety Precautions:
It is crucial to handle 4-Methoxy-4'-nitrostilbene with care, as it may pose health risks if ingested or inhaled, and can cause skin and eye irritation upon contact. Proper safety measures should be taken during its production, storage, and use to minimize potential hazards.

Upstream product

• 104-03-0 4-nitrobenzeneacetic acid 
• 123-11-5 4-methoxy-benzaldehyde 
• 6933-17-1 (4-nitrobenzylidene)triphenylphosphorane 
• 36134-65-3 3-(4-methoxy-phenyl)-2-(4-nitro-phenyl)-acrylic acid 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 100-13-0 4-nitrostyrene 
• 2767-70-6 (p-nitrobenzyl)triphenylphosphonium bromide 
• 637-69-4 4-Methoxystyrene 
• 456-27-9 4-nitrobenzenediazonium tetrafluoroborate 
• 586-78-7 para-nitrophenyl bromide 
• 99-99-0 1-methyl-4-nitrobenzene 
• 100-00-5 4-chlorobenzonitrile 
• 636-98-6 p-nitrobenzene iodide 
• 1145-93-3 diethyl 4-methoxybenzylphosphonate 

Downstream Products

• 7314-07-0 4-amino-4'-methoxystilbene 
• 15794-99-7 (α,α'-dibromo-4'-nitro-bibenzyl-4-yl)-methyl ether 
• 14802-10-9 4-[2-(4-methoxyphenyl)ethyl]aniline 
• 39082-36-5 (α'-bromo-4'-nitro-stilben-4-yl)-methyl ether 
• 1258785-37-3 2-(4-methoxyphenyl)-3-(4-nitrophenyl)-2H-azirine 
• 1186335-71-6 4,5,6,7-tetrachloro-2-(4-(4-methoxyphenethyl)phenyl)isoindoline-1,3-dione 
• 1608492-51-8 (2R,3S,4R,5S)-2,5-bis(4-methoxyphenyl)-3,4-bis(4-nitrophenyl)tetrahydrofuran 
• 14987-61-2 1-methoxy-4-(4-nitrophenethyl)benzene 
• 1203558-95-5 4-[(4'-methoxyldiphenylethylene-4-ylimino)methyl]phenol 
• 1253645-34-9 2-[(4'-methoxyldiphenylethylene-4-ylimino)methyl]phenol 
• 102549-09-7 (E)-N-(4-(4-methoxystyryl)phenyl)benzamide 

Relevant academic research and scientific papers

Synthesis, growth, structural, optical, spectral, thermal and mechanical studies of 4-methoxy 4-nitrostilbene (MONS): A new organic nonlinear optical single crystal

4-Methoxy 4-nitrostilbene (MONS), a new organic nonlinear optical material has been synthesized. Based on the solubility data good quality single crystal with dimensions up to 38 × 11 × 3 mm3 has been grown by slow evaporation method using ethyl methyl ketone (MEK) as a solvent. Powder XRD confirms the crystalline property and also the diffraction planes have been indexed. The lattice parameters for the grown MONS crystals were determined by using single crystal X-ray diffraction analysis and it reveals that the crystal lattice system is triclinic. The crystalline perfection of the grown crystals has been analysed by high resolution X-ray diffraction (HRXRD) rocking curve measurements. Fourier transform infrared (FTIR) spectrum for powdered MONS sample confirms the functional groups present in the grown crystal. The UV-vis absorption spectrum has been recorded in the range of 190-1100 nm and the cut off wavelength 499 nm has been determined. The optical constants of MONS have been determined through UV-vis-NIR spectroscopy. The MONS crystals were further subjected to other characterizations. i.e., 1H NMR, TG/DTA, photoluminescence and microhardness test. The Kurtz and Perry powder technique confirms the NLO property of the grown crystal and the SHG efficiency of MONS was found to be 1.55× greater than that of KDP crystal.

Immobilized Pd on a NHC-functionalized metal-organic FrameworkMIL-101(Cr): An efficient heterogeneous catalyst in the heck and copper-free Sonogashira coupling reactions

A heterogeneous palladium catalyst system based on immobilization of palladium moieties on a N-heterocyclic carbene (NHC) modified metal organic framework (MOF) was developed for the Heck and copper-free Sonogashira coupling reactions. In order to prepare this catalyst system, first, MIL-101(Cr) was functionalized with NHC moieties through a post synthetic modification (PSM) approach, and then Pd metal was stabilized on the prepered MIL-101(Cr)-NHC substrate. This material was characterized using various microscopic and spectroscopic techniques and then was used as an efficient heterogeneous Pd catalyst system in the Heck and copper-free Sonogashira reactions. Results of the heterogeneity tests showed that the Pd-NHC-MIL-101(Cr) catalyst can efficiently catalyzed these coupling reactions heterogeneously and no remarkable changes observed in the morphology and structure of MIL-101(Cr) template during the reaction progress. Also, existence of palladium nanoparticles immobilized on the MOF structure affirmed by the TEM and XPS analysis confirmed the oxidation state of Pd. A variety of alkene and alkyne derivatives were synthesized in good to excellent yields using this heterogeneous Pd catalyst system under normal conditions. More importantly Pd-NHC-MIL-101(Cr) catalyst was simply recovered from the reaction medium without remarkable decreasing in its catalytic activities after five times of reusability. The ICP analysis showed the very low Pd and Cr metals leaching, representing high stability and applicability of this catalyst in Pd coupling reactions.

New Bidentate N-Sulfonyl-Substituted Aromatic Amines as Chelate Ligand Backbones: Pd Catalyst Generation in C-C Coupling via in Situ and Precatalyst Modes

A series of six new, bidentate ligands based on N-(2-(R-sulfonamido)benzyl)R-sulfonamide have been isolated as dianionic or monoanionic chelators via condensation of 2-(aminomethyl)aniline with sulfonyl chloride reagents; R = methyl (1 and 1′), tolyl (2 and 2′), 2,4,6-Trimethylphenyl (3), or 2,4,6-Triisopropylphenyl (4). Complexes of ligands 2-4 reacted at room temperature with palladium(ii) acetate in the presence of various monodentate N-donor co-ligands to form complexes Pd2(2dmap), Pd2′(OAc.py), Pd3(2acn), Pd3(2py), Pd4(2acn), and Pd4(2py), which were structurally confirmed by three X-ray crystal analyses. Results of catalysis studies in water showed high turnover frequencies and yields of up to 98 % within 10 min and at 0.2 mol-% palladium catalyst loading. Relative to ligand-free catalysis in the presence of only Pd(OAc)2, the ligand-supported palladium species clearly possess positive catalytic advantage. Furthermore, Suzuki coupling efficiencies by 1: 1 'Pd(OAc)2 + ligand' yielded notably better outcomes than for the 1: 2 'Pd(OAc)2 + ligand' in situ catalyst generation, which reveals that coordinative saturation is undesirable. The size of the complementing monodentate co-ligand was observed to influence the catalytic efficiency such that bulkier co-ligands consistently yielded improved turnover frequency values, which leads to the conclusion that steric repulsion between the synthesised ligands and the bulkier co-ligands aided the generation of vacant coordination sites for the more active complexes. Moderate Heck coupling activity was recorded for the complexes and better activities appear to correlate with moderate bulkiness of ligand 3.

Multidentate N-Heterocyclic Carbene Complexes of Nickel and Palladium: Structural Analysis and Catalytic Application in Mizoroki–Heck Coupling Reaction

Two series of electron-rich metal (Ni and Pd) complexes, namely a pyridine-coordinated tridentate NHC/amidate/phenoxy metal complex and a tetradentate complex bearing an extra pyridyl group, were synthesized. Two carbene moieties, imidazole-based and benzimidazole-based NHCs, were also incorporated into the ligand backbones. Seven of the new complexes were structurally characterized and comparative structural analysis revealed that the tetradentate complex with a flanking pyridyl side-arm was less distorted, leading to chelation-assisted stronger NHC coordination and hence a shorter metal–carbene bond. The catalytic activities of the two sets of palladium complexes for the Mizoroki–Heck coupling reaction were investigated. The comparative data showed that despite the higher thermal stability and the presence of the flanking hemilabile pyridyl side-arm which provided unsaturation to the metal center, the catalytic performance was slightly inferior to that of the tridentate palladium complex with a “throw-away” pyridine ligand. The tridentate palladium complex with the benzimidazole-based NHC moiety was the most effective catalyst, allowing the utilization of a range of aryl chlorides including deactivated substrates with a low 0.2 mol-% Pd loading in molten n-tetrabutylammonium bromide.

Promising new catalytic properties of a Co (II)-carboxamide complex and its derived Co3O4 nanoparticles for the Mizoroki-Heck and the Epoxidation reactions

The new Co(II) - carboxamide complex (1) and Co3O4 nanoparticles (2), by way of thermal decomposition of (1) have been efficiently synthesised in the environment-friendly. X-ray diffraction reveals a slightly distorted octahedral coordination of cobalt (four nitrogens and two oxygens) in (1) and regular octahedral or tetrahedral ones (oxygens only) in (2). The investigation of (1) and (2) in the Mizoroki-Heck and epoxidation of alkens reactions showed them both to be powerful, green and inexpensive catalysts.

Development of Tetrachlorophthalimides as Liver X Receptor β (LXRβ)-Selective Agonists

Liver X receptor (LXR) agonists are candidates for the treatment of atherosclerosis via induction of ABCA1 (ATP-binding cassette A1) gene expression, which contributes to reverse cholesterol transport (RCT) and to cholesterol efflux from the liver and intestine. However, LXR agonists also induce genes involved in lipogenesis, such as SREBP-1c (sterol regulatory binding element protein 1c) and FAS (fatty acid synthase), thereby causing an undesirable increase in plasma and hepatic triglyceride (TG) levels. Recent studies indicate that LXRα contributes to lipogenesis in liver, and selective LXRβ activation improves RCT in mice. Therefore, LXRβ-selective agonists are promising candidates to improve atherosclerosis without increasing plasma or hepatic TG levels. However, the ligand-binding domains in the two LXR isoforms α/β share high sequence identity, and few LXR ligands show subtype selectivity. In this study we identified a tetrachlorophthalimide analogue as an LXRβ-selective agonist. Structural development led to (E)-4,5,6,7-tetrachloro-2-(2-styrylphenyl)isoindoline-1,3-dione (24 a), which shows potent and selective LXRβ agonistic activity in reporter gene assays. In binding assays, compound 24 a bound to LXRβ preferentially over LXRα. It also induced the expression of ABCA1 mRNA but not SREBP-1c mRNA in cells. Compound 24 a appears to be a promising lead compound for therapeutic agents to treat atherosclerosis without the side effects induced by LXRα/β dual agonists.

Synthesis of polystyrene-supported Pd(II)-NHC complex derived from theophylline as an efficient and reusable heterogeneous catalyst for the Heck-Matsuda cross-coupling reaction

The polystyrene-supported palladium(II)-N-heterocyclic carbene complex PS-NHC-Pd(II) was successfully synthesized from theophylline as an environmentally benign NHC precursor, using chloromethylated polystyrene resin. The PS-NHC-Pd(II) complex was characterized by various techniques including Fourier transform infrared spectroscopy (FTIR), energy dispersive X-ray spectroscopy (EDX), thermal analysis (TGA-DTG), inductively coupled plasma (ICP), and CHN elemental analysis. The morphology of the polymer beads was also studied using scanning electron microscope. The polymer supported Pd(II)-NHC complex exhibits excellent catalytic activity and stability for the Heck-Matsuda cross-coupling reaction under mild conditions. A variety of arenediazonium tetrafluoroborate salts was coupled with the olefinic substrates in ethanol, in the presence of the 0.9 mol% of the catalyst to afford the corresponding cross-coupling adducts in high yields under aerial conditions. Moreover, the heterogeneous catalyst can be easily recovered by simple filtration and reused for seven cycles without significant loss in its activity.

Stilbene-benzophenone dyads for free radical initiating polymerization of methyl methacrylate under visible light irradiation

The AB and AB2 trans-stilbene-benzophenone dyads were synthesized through multi-step pathway. The target dyads showed remarkable absorption in visible light region. Visible light photoinitiating polymerization of methyl methacrylate by the new dyads was studied by photo-differential scanning calorimetry. The results suggested that the AB2 dyad showed more efficient photoinitiating polymerization of methyl methacrylate than the AB one under visible light irradiation. Furthermore, the new dyads yielded the greater visible light photoinitiaing polymerization effect than the intermolecular photoinitiating systems and the commercial photoinitiator titanocene respectively. The molecular weights of visible light photopolymers produced by the new dyads were determined by gel permeation chromatography. The visible light photoinitiating mechanism of the new dyads was analyzed by the static and transient absorption and emission spectra, electron spin resonance spectra and cyclic voltammograms. The thermal stabilities of the new dyads were further studied by differential scanning calorimetry and thermograving.

A stilbene compound of preparation method

The invention provides a preparation method of toluylene compounds. A deep eutectic solvent formed by use of choline chloride and amide is taken as a reaction solvent, and substituted or unsubstituted diethyl benzylphosphonate and substituted or unsubstituted benzaldehyde are taken as raw materials to have a Wittig-Horner reaction under catalysis of an alkali, and consequently, the toluylene compounds can be obtained. According to the preparation method, the deep eutectic solvent formed by use of choline chloride and amide is taken as the reaction solvent, and the solvent is suitable for the synthesis of the toluylene compounds; the preparation method has the advantages of good universality, mild reaction conditions, convenient operations, low cost, environmental friendliness and the like, and is suitable for industrial production.

Polyaniline-anchored palladium catalyst-mediated Mizoroki-Heck and Suzuki-Miyauraa reactions and one-pot Wittig-Heck and Wittig-Suzuki reactions

A polyaniline-anchored palladium catalyst was prepared and screened for coupling reactions of aryl halides. The robust and recyclable catalyst was effective in Mizoroki-Heck and Suzuki-Miyaura reactions of aryl bromides and aryl iodides. The catalyst system was further employed for one-pot Wittig-Heck and Wittig-Suzuki combinations to build conjugated compounds in good conversions.