411206-92-3

Usage

Uses

Used in Organic Synthesis:
4-(3-Nitrophenyl)benzaldehyde is used as a key intermediate in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its unique structure allows for versatile chemical reactions, making it a valuable building block in organic chemistry.
Used in Research and Laboratory Settings:
4-(3-Nitrophenyl)benzaldehyde is employed as a reagent in research and laboratory settings for the development and optimization of chemical reactions and processes. Its distinct properties enable researchers to study and understand the behavior of various chemical systems, contributing to the advancement of scientific knowledge.
Used in Analytical Chemistry:
In analytical chemistry, 4-(3-Nitrophenyl)benzaldehyde is utilized as a derivatizing agent for the detection and quantification of specific compounds. Its reactivity with certain functional groups allows for the formation of derivatives that can be easily analyzed using various analytical techniques, such as chromatography and spectroscopy.
Used in Material Science:
4-(3-Nitrophenyl)benzaldehyde is also employed in material science for the development of novel materials with specific properties. Its incorporation into polymers, for example, can result in materials with improved thermal stability, mechanical strength, or other desirable characteristics.

Upstream product

• 1122-91-4 4-bromo-benzaldehyde 
• 585-79-5 m-nitrobromobenzene 
• 87199-17-5 4-formylphenylboronic acid, 
• 13331-27-6 m-nitrobenzene boronic acid 
• 645-00-1 m-iodonitrobenzene 
• 873-76-7 para-Chlorobenzyl alcohol 
• 121-73-3 3-Nitrochlorobenzene 
• 59016-93-2 p-hydroxymethylphenylboronic acid 
• 104-88-1 4-chlorobenzaldehyde 
• 873-75-6 4-bromobenzenemethanol 
• 18282-51-4 4-iodo-benzyl alcohol 
• 880158-11-2 4-hydroxymethyl-3'-nitrobiphenyl 

Downstream Products

• 1197335-46-8 methyl (2S,5E)-2-(tritylamino)-4-oxo-6-(3′-nitrobiphen-4-yl)-hex-5-enoate 
• 1410776-33-8 methyl (2S,6R)-4-oxo-6-(3′-nitrobiphen-4-yl)piperidine-2-carboxylate 

Relevant academic research and scientific papers

Palladium catalyzed Suzuki cross-coupling reactions using N,O-bidentate ligands

Palladium-catalyzed Suzuki cross-coupling reactions employing Schiff-bases as ligands toward a series of substituted arylbromides and boronic acids were pursued. In the presence of N,O-bidentate ligand, 2-[1-(2,4,6-trimethyl- phenylimino)-ethyl]-phenol 5, the catalytic reactions could be carried out efficiently at room temperature with a wide array of arylbromides, even with electronically deactivated arènes. A deprotonated 5, 5′, chelated palladium acetate complex, [5′Pd(II)(OAc)(solv)] 8, was proposed as a precursor of a genuine catalytically active species.

Bimetallic docked covalent organic frameworks with high catalytic performance towards coupling/oxidation cascade reactions

Covalent organic frameworks (COFs) are an emerging class of crystalline porous polymers that make these materials suitable for use as excellent scaffold in heterogeneous catalysis. Here we synthesize a layered two-dimensional (2D) COF (TADP-COF) through the condensation reaction between four-branched 5,10,15,20-tetrakis(4-aminophenyl)porphyrin (TAPP) and linear 2,5-dihydroxyterephthalaldehyde (Dha) and 1,4-phthalaldehyde (PA) building blocks. Porphyrin units, imine and hydroxyl groups together with imines can provide wide coordination sites for metal docking. Using a programmed synthetic procedure, Cu(ii) ions first coordinated with the imine groups in conjunction with their adjacent hydroxyl groups, and porphyrin units and subsequently added Pd(ii) ions occupied the remaining imine sites in the space between adjacent COF layers. The bimetallic Pd(ii)/Cu(ii)@TADP-COF showed high catalytic activity in a one-pot coupling/oxidation cascade reaction in water. The high surface area, one-dimensional (1D) open channel structure and predesigned catalytic active sites of this material make it ideal candidate for use as heterogeneous catalyst in a wide range of catalytic reactions.

The Discovery of Novel ACA Derivatives as Specific TRPM2 Inhibitors that Reduce Ischemic Injury Both in Vitro and in Vivo

The transient receptor potential melastatin 2 (TRPM2) channel is associated with ischemia/reperfusion injury, inflammation, cancer, and neurodegenerative diseases. However, the limit of specific inhibitors impedes the development of TRPM2-targeted therapeutic agents. To discover more potent and selective TRPM2 inhibitors, 59 N-(p-amylcinnamoyl) anthranilic acid (ACA) derivatives were synthesized and evaluated using calcium imaging and electrophysiology approaches. Systematic structure-activity relationship studies resulted in some potent compounds inhibiting the TRPM2 channel with sub-micromolar half-maximal inhibitory concentration values. Among them, the preferred compound A23 exhibited TRPM2 selectivity over TRPM8 and TRPV1 channels as well as phospholipase A2 and showed neuroprotective activity in vitro. Following pharmacokinetic studies, A23 was further evaluated in a transient middle cerebral artery occlusion model in vivo, which significantly reduced cerebral infarction. These data indicate that A23 might serve as a useful tool for TRPM2-related research as well as a lead compound for the development of therapeutic agents for ischemic injury.

Monosubstituted, Anionic Imidazolyl Ligands from N?H NHC Precursors and Their Activity in Pd-Catalyzed Cross-Coupling Reactions

We report that treatment of several 2-diphenylphosphinoimidazoles with Pd(II) salts generates monosubstituted N?H NHC?Pd complexes via insertion into the C?P bond. Removal of the N?H proton in situ leads to anionic (X-type) or imidazolyl-Pd complexes that are highly stable and catalytically active, achieving up to 340,000 turnovers at 1 ppm catalyst loading in Suzuki-Miyaura reactions. DFT-calculated Tolman electronic parameters for the sterically small ligands suggest that these ligands are significantly more donating than traditional NHCs, which provides a rationale for rapid cross-coupling catalysis. Excellent reactivity is also demonstrated in Sonogashira reactions. (Figure presented.).

Antioxidant properties of synthesis nanometallic Pd-Ni?2-mercaptoethanol as effective catalyst for suzuki-miyaura reactions

The palladium-catalyzed Suzuki coupling reaction is one of the most efficient strategies for constructing a carbon-carbon bond. In recent years, bimetallic catalysts have become candidates for the Suzuki coupling reaction. In this work, Pd-Ni?2-Mercaptoethanol nanoparticles were synthesized for the Suzuki-Miyaura cross-coupling of arylboronic acids with aryl bromides, in the N,N-dimethylformamide/water mixture catalyzed by Pd-Ni: A simple and efficient reaction performed in a solvent, without a ligand, and in open air. We found that the Suzuki-Miyaura reactions are remarkably fast (5 min), with high yields and the products are highly pure. The Pd-Ni?2-Mercaptoetanol nanoparticles have a narrow size distribution with a mean crystallite size of 10 nm. Radical scavenging activities of the complexes have been evaluated by using DPPH, DMPD+ and ABTS+ assays. IC50 values (μg/ml) of the complexes and standards on DPPH, DMPD+ and ABTS+ respectively following the sequences.

Palladium-catalyzed denitrative Sonogashira-type cross-coupling of nitrobenzenes with terminal alkynes

Described herein is a palladium-catalyzed cross-coupling reaction between nitroarenes and terminal alkynes, offering a facile method for C(sp2)-C(sp) bond formation. The utility of this protocol has been proven by the construction of polycyclic aromatic hydrocarbons (PAHs) and orthogonal cross-coupling.

Pd-Au-Y as Efficient Catalyst for C-C Coupling Reactions, Benzylic C-H Bond Activation, and Oxidation of Ethanol for Synthesis of Cinnamaldehydes

Pd-Au nanoalloy supported on zeolite-Y (Pd-Au-Y) matrix was found to be an effective catalyst for C-Cl bond activation and oxidative coupling of 2-naphthol, leading to the formation of various biaryl products and 1,1′-bi-2-naphthol, BINOL. The same catalyst was also highly efficient for selective oxidation of benzylic alcohols to benzaldehydes. Cinnamaldehydes were obtained directly from benzaldehydes by aldol condensation with acetaldehyde generated in situ by partial oxidation of ethanol in the presence of Pd-Au-Y catalyst at 120 °C under basic condition. The biaryl products were also obtained directly from benzylic alcohols in a one-pot system by reacting with phenylboronic acid. The formation of biaryls from benzylic alcohols was believed to occur via one-pot benzylic C-H and C-Cl bond activation. A high % yield of biaryls, BINOL, aldehydes, and cinnamaldehydes was obtained by performing different reactions using the single Pd-Au-Y catalyst. The strong interaction of chloro-benzylic alcohol was predominantly located at active gold species. X-ray photoelectron and diffuse reflectance spectroscopic studies revealed the strong interaction between Pd and Au particles. Electrochemical studies provided proper evidence for the individual role of the nanoparticles (NPs) in one-pot synthesis of biaryls from benzylic alcohols.

Novel chiral bis-phosphoramides as organocatalysts for tetrachlorosilane-mediated reactions

The formation of novel chiral bidentate phosphoroamides structures able to promote Lewis base-catalyzed Lewis acid-mediated reactions was investigated. Two different classes of phosphoroamides were synthetized: the first class presents a phthalic acid/pri

Poly(: O -aminothiophenol)-stabilized Pd nanoparticles as efficient heterogenous catalysts for Suzuki cross-coupling reactions

Poly(o-aminothiophenol) (PATP)-stabilized Pd nanoparticles with Pd nanoparticles embedded in a polymer matrix have been obtained through a facile one-step route by mixing o-aminothiophenol monomer and Pd(NO3)2 in an acidic aqueous solution without additional template or surfactant. The redox reaction between o-aminothiophenol and Pd(NO3)2 leads to the simultaneous formation of a PATP polymer and Pd nanoparticles. The PATP-stabilized Pd nanoparticles have been characterized by TEM, FTIR, XRD, ICP-MS and XPS. Catalytic results showed that PATP-stabilized Pd nanoparticles were highly stable and active catalysts for Suzuki cross-coupling reactions, where high yields could be achieved with arylboronic acid and aryl halides bearing a variety of substituents.

VP1 crystal structure-guided exploration and optimization of 4,5-dimethoxybenzene-based inhibitors of rhinovirus 14 infection

Human rhinoviruses (HRV) are the predominant cause of common colds and flu-like illnesses, but are also responsible for virus-induced exacerbations of asthma and chronic obstructive pulmonary disease. However, to date, no drug has been approved yet for clinical use. In this study, we present the results of the structure-based lead optimization of a class of new small-molecule inhibitors that we previously reported to bind into the pocket beneath the canyon of the VP1 protein. A small series of analogues that we designed based on the available structure and interaction data were synthesized and evaluated for their potency to inhibit the replication of HRV serotype 14. 2-(4,5-Dimethoxy-2-nitrophenyl)-1-(4-(pyridin-4-yl)phenyl)ethanol (3v) was found to be a potent inhibitor exhibiting micromolar activity (EC50 Combining double low line 3.4 ± 1.0 μM) with a toxicity for HeLa cells that was significantly lower than that of our previous hit (LPCRW-0005, CC50 Combining double low line 104.0 ± 22.2 μM; 3v, CC50 > 263 μM).