1137-77-5

Usage

Uses

Used in Organic Synthesis:
4'-METHOXY-BIPHENYL-4-YLAMINE is used as a reagent in organic synthesis for its ability to participate in a wide range of chemical reactions, such as coupling, condensation, and substitution processes. Its presence can lead to the formation of new compounds with diverse applications in various industries.
Used in Spectral Analysis:
In the field of spectral analysis, 4'-METHOXY-BIPHENYL-4-YLAMINE is utilized as a reagent to assist in the identification and characterization of other compounds. Its unique spectral properties can help in determining the structure and composition of unknown substances, making it a valuable tool for researchers and analysts.

Upstream product

• 100-66-3 methoxybenzene 
• 100-65-2 N-Phenylhydroxylamine 
• 5720-07-0 4-methoxyphenylboronic acid 
• 540-37-4 p-aminoiodobenzene 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 89415-43-0 (4-aminophenyl)boronic acid 
• 2143-90-0 4-methoxy-4'-nitrobiphenyl 
• 58970-19-7 4-chloro-(4'-methoxybiphenyl) 
• 126971-87-7 4-iodo-4’-methoxy-1,1’-biphenyl 
• 33397-21-6 tris(4-methoxyphenyl)bismuth 
• 24067-17-2 4-nitrophenylboronic acid 
• 100-01-6 4-nitro-aniline 
• 586-78-7 para-nitrophenyl bromide 
• 106-47-8 4-chloro-aniline 

Downstream Products

• 18158-44-6 4-dimethylamino-4'-methoxybiphenyl 
• 1360630-64-3 6-methoxy-N-(4'-methoxybiphenyl-4-yl)naphthalene-2-sulfonamide 
• 1237534-12-1 3,4-dibromo-1-(4'-methoxybiphenyl-4-yl)-1H-pyrrole-2,5-dione 
• 34008-11-2 (CH₃)3SnC₆H₄-p-CHNC₆H₄-p-C₆H₄-p-OCH₃ 

Relevant academic research and scientific papers

Nickel-catalyzed monoarylation of ammonia

Structurally diverse (hetero)aryl chloride, bromide, and tosylate electrophiles were employed in the Ni-catalyzed monoarylation of ammonia, including chemoselective transformations. The employed JosiPhos/[Ni(cod)2] catalyst system enables the use of commercially available stock solutions of ammonia, or the use of ammonia gas in these reactions, thereby demonstrating the versatility and potential scalability of the reported protocol. Proof-of-principle experiments established that air-stable [(JosiPhos)NiCl2] precatalysts can be employed successfully in such transformations. Lighten Up: The substrate scope of the title reaction includes (hetero)aryl chloride, bromide, and tosylate electrophiles. The versatility and potential scalability of the reported method is demonstrated by the use of either commercially available stock solutions of ammonia or ammonia gas.

Microwave-assisted Suzuki-Miyaura reactions with an insoluble pyridine-aldoxime Pd-catalyst

The preparation of a solid Pd(II)-precatalyst and its use in microwave-assisted Suzuki-Miyaura reactions in water is described. The precatalyst is obtained by treatment of 4-pyridine-aldoxime with Na 2PdCl4 and is insoluble in organic solvents as well as in water. Its robustness under microwave conditions and its insolubility allows simple reuse in 'teabags'.

Liquid-Assisted Grinding Accelerating: Suzuki-Miyaura Reaction of Aryl Chlorides under High-Speed Ball-Milling Conditions

The effect of liquid-assisted grinding has been studied using mechanical Suzuki-Miyaura reaction of aryl chlorides as the model reaction. Catalytic systems of Davephos and PCy3 are tested respectively showing strong influences from different liquids. Unexpected improvement of yield over 55% is observed using alcohols as additives, which is explained by in situ formed alkoxides and their participation in oxidative addition. Further expansion of substrates using Pd(OAc)2/PCy3/MeOH system gives desired products in good to high yields.

Multiplexed CuAAC Suzuki-Miyaura Labeling for Tandem Activity-Based Chemoproteomic Profiling

Mass-spectrometry-based chemoproteomics has enabled the rapid and proteome-wide discovery of functional and potentially 'druggable' hotspots in proteins. While numerous transformations are now available, chemoproteomic studies still rely overwhelmingly on

Base-Free Suzuki–Miyaura Coupling Reaction Using Palladium(II) Supported Catalyst in Water

Abstract: The carbon–carbon bond formation via Suzuki–Miyaura reaction was performed in water as green solvent. Pd(OAc)2(PPh3)2 supported on magnesium hydroxide and cerium carbonate hydroxide composite was prepared and characterized by various techniques. The cross-coupling reaction of aryl halides carried out in water using mild conditions. The effects of temperature, solvents, the amount of catalyst and leaving groups were studied to find the optimization conditions for cross-coupling reaction. Various aryl halides were smoothly transformed into the biaryls in good yields. In addition, the catalyst also exhibited stability and catalytic performance in the cross-coupling of aryl halides. Graphical Abstract: [Figure not available: see fulltext.] A new approach is developed for carbon–carbon bond formation via Suzuki–Miyaura reaction.2 Pd(OAc)2(PPh3)2?supported on mixed magnesium hydroxide and cerium carbonate hydroxide were prepared and characterized by XRD, XPS, SEM–EDX techniques. The cross-coupling reaction of aryl halides can be carried out in water and under mild conditions (80 °C).

Nanoparticulate palladium catalyst stabilized by supported on feather keratin for Suzuki coupling reaction

Palladium nanoparticles supported in a feather keratin matrix were efficient catalyst for the coupling reactions of aryl bromides with arylboronic acid in aqueous medium under mild reaction conditions. The biopolymer-based catalyst demonstrated excellent activity for substrates with a wide range of functional groups. The product biaryls were precipitated from the reaction mixture with good to excellent yields and purities. The catalyst was recovered from the reaction solution easily by simple filtration, and can be reused at least seven times.

Magnetic chitosan-functionalized cobalt-NHC: Synthesis, characterization and catalytic activity toward Suzuki and Sonogashira cross-coupling reactions of aryl chlorides

Aryl chlorides are one of the most stable and available electrophiles, however, their coupling with nucleophiles remains a challenge in organic synthesis. Herein, we prepared a Cobalt-NHC (N-Heterocyclic carbene) complex anchored on magnetic chitosan nanoparticles and assayed its catalytic activity for the reactions of substituted phenylboronic acid and also phenlacetylene with derivatives of aryl chlorides. These reactions are of great importance since they are employed for the synthesis of unsymmetrical diarylethynes and biphenyls, which belong to a prime class of building blocks. The synthesized nanocatalyst was found to be highly efficient in Suzuki and Sonogashira coupling in terms of their activity and recyclability in polyethylene glycol (PEG) as a green reaction media under conditions of temperatures (70 and 100 °C) and Co loading (3 and 6 mol%). To the best of our knowledge, this is the first attempt of using cobalt-NHC complex for catalyzing the abovementioned reactions. Moreover, replacing the earth-abundant Cobalt-based catalyst as an alternative to high cost palladium make this approach promising from sustainable chemistry view.

Room-Temperature Aqueous Suzuki-Miyaura Cross-Coupling Reactions Catalyzed via a Recyclable Palladium@Halloysite Nanocomposite

A reliable method for encapsulation of palladium nanoparticles (6-8 nm particles) in halloysite (Pd@Hal) has been developed. The Pd@Hal was found to be a highly efficient room-temperature catalyst for Suzuki-Miyaura cross-coupling reactions that gave high yields of a diverse array of coupling products in 5:2 n-PrOH/H2O within 1 h. The catalytic system was remarkably effective with a broad substrate scope. In addition, the catalyst was easily recovered and recycled without a significant loss of catalytic activity.

Assembly immobilized palladium(0) on carboxymethylcellulose/Fe3O4 hybrid: An efficient tailor-made magnetically catalyst for the Suzuki–Miyaura couplings

The Pd nanoparticles (Pd NPs) embedded on magnetically retrievable carboxymethylcellulose/Fe3O4 (Pd0@CMC/Fe3O4) organic/inorganic hybrid were prepared via the conventional simple process. The presence of the hydroxyl and carboxyl groups within the framework of the magnetic hybrid enables the facile preparation and stabilization of Pd NPs in this organic/inorganic hybrid. This hybrid catalyst was very effective in the Suzuki–Miyaura reaction of a variety of aryl halides with arylboronic acid to afford excellent product yields. The catalyst showed good stability and could be easily recovered with an external magnetic field and reused for several times without a significant loss in its catalytic activity. Furthermore, the Pd0@CMC/Fe3O4 hybrid catalyst was fully characterized by UV–Vis, FT–IR, XRD, SEM, EDX, TEM, XPS and TGA techniques. The hot filtration test suggests that a homogeneous mechanism is operative in Suzuki–Miyaura reaction.

Safe palladium-catalyzed cross-couplings with microwave heating using continuous-flow silicon carbide reactors

Herein we present a 200 mm × 3 mm i silicon carbide (SiC) tube reactor for use in a commercially available microwave heated continuous-flow system. The SiC flow reactor enables palladium(0)-catalyzed reactions that, due to precipitation and subsequent hot spot formation, often followed by reactor failure, are unsuitable to conduct in standard microwave-transparent borosilicate glass reactors. We report continuous-flow protocols for the Mizoroki-Heck reaction (10 examples, 81-86% yield) as well as the Suzuki-Miyaura cross-coupling (14 examples, 70-87% yield), showing the utility of the SiC reactor. Furthermore, we performed a scale-out of the NSAID biphenylacetic acid, achieving outputs of 14 mmol/h of the Suzuki-Miyaura reaction, and a 72% overall yield over three steps. The SiC reactor enabled fast and efficient temperature control, high robustness, and easy maintenance.