6242-97-3

Usage

Uses

Used in Electronics Industry:
4-Chloro-4'-nitrobiphenyl is used as a chemical intermediate for the synthesis of various electronic components, such as semiconductors and other materials with specific electronic properties. Its unique structure and functional groups contribute to the desired characteristics of these components.
Used in Scientific Research:
4-Chloro-4'-nitrobiphenyl is employed as a research compound in various scientific studies, particularly those focused on the development and understanding of new materials for electronics and semiconductors. Its properties and interactions with other compounds are of interest to researchers in the field.

Upstream product

• 636-98-6 p-nitrobenzene iodide 
• 14064-15-4 (4-chlorophenyl)trimethylstannane 
• 100-01-6 4-nitro-aniline 
• 108-90-7 chlorobenzene 
• 1679-18-1 4-Chlorophenylboronic acid 
• 100-00-5 4-chlorobenzonitrile 
• 4482-01-3 o-benzenedisulfonimide 

Downstream Products

• 135-68-2 4-(4-chlorophenyl)aniline 
• 69936-46-5 2-Amino-5-<4-chlor-phenyl>-benzophenon 
• 515879-13-7 4'-chloro-4-nitro-biphenyl-3-carboxylic acid [3-methoxy-4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amide 
• 909783-72-8 4-amino-4'-chloro-biphenyl-3-carboxylic acid [3-methoxy-4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amide 
• 69936-40-9 5-(4-chloro-phenyl)-3-phenyl-benzo[c]isoxazole 

Relevant academic research and scientific papers

Pd-Catalysed Suzuki-Miyaura cross-coupling of aryl chlorides at low catalyst loadings in water for the synthesis of industrially important fungicides

The Suzuki-Miyaura coupling reaction of electron-poor aryl chlorides in the synthesis of crop protection-relevant active ingredients in water is disclosed. Optimisation of the reaction conditions allowed running the reaction with 50 ppm of Pd-catalyst loading without an additional organic solvent in the cross-coupling reaction step in short reaction times. The system was optimised for the initial cross-coupling step of the large scale produced fungicides Boscalid, Fluxapyroxad and Bixafen up to 97% yield. It is also shown that the Suzuki-Miyaura reaction can be easily scaled up to 50 g using a simple product separation and purification using environmentally benign solvents in the work-up. To show the usability of this method, it was additionally applied in the three-step synthesis of the desired active ingredients.

An unsymmetrical Schiff-base derived recyclable Pd-catalyst for Suzuki–Miyaura and Sonogashira reactions in aqueous media

Abstract: A water-soluble palladium (II) complex containing an unsymmetrical Schiff-base ligand was synthesized and applied as catalyst Suzuki–Miyaura and Sonogashira cross-coupling reactions in aqueous media. Notably, moderate to excellent yields of biaryls were obtained in Suzuki reaction with usually less reactive aryl and heteroaryl chlorides under relatively mild condition. Moderate-to-high yields of aryl-alkynes were also obtained in Sonogashira reactions using aryl bromides. Apart from hydrophilic nature, the accomplishment of reactions in water, high recyclability, broad functional group tolerance, etc., are other advantages of the system. Graphic abstract: [Figure not available: see fulltext.]

Anchoring Pd(OAc)2 on amide-bonded covalent organic frameworks: An efficient heterogeneous Pd@OC-MA catalyst for Suzuki-Miyaura coupling reactions in water

Nitrogen-rich of a melamine-based mesoporous covalent organic frameworks (COFs) materials were synthesized and used as a carrier to support a Pd(OAc)2. The Pd@OC-MA revealed an efficient catalytic activity and selectivity for Suzuki-Miyaura coupling reactions in an environmentally friendly water medium at room temperature. Specifically, it had moderate to excellent conversion for inactive chlorinated aromatic hydrocarbons. The catalyst was synthesized simply, had high stability and good selectivity, and was easy to recycle. Excellent catalytic activity of the Pd@OC-MA was also observed after five consecutive cycles.

Gold catalysed Suzuki-Miyaura coupling of arenediazonium o-benzenedisulfonimides

Arenediazonium o-benzenedisulfonimides have been used as efficient electrophilic partners in Au(I) catalysed Suzuki coupling reactions. The synthetic protocol is general, easy and produced either biaryls or heteroaryl arenes in good yields (51 positive examples, average yield 80%). o-Benzenedisulfonimide was recovered at the end of the reactions and was reused to prepare the starting salts for further reactions. Mechanistic insights suggest that the o-benzenedisulfonimide anion act as an electron transfer agent and promotes a catalytic cycle which does not require the presence of photocatalysts or external oxidants.

Facile Synthesis of Magnetic Hierarchical Core–Shell Structured Fe3O4@PDA-Pd@MOF Nanocomposites: Highly Integrated Multifunctional Catalysts

A magnetic hierarchical core–shell structured Fe3O4@PDA-Pd@[Cu3(btc)2] nanocomposite has been fabricated via a facile layer-by-layer assembly method. It contains a core of polydopamine (PDA)-modified magnetic Fe3O4 nanoparticles (NPs), a transition layer of Pd NPs, and a porous outer shell of copper-based metal–organic framework (MOF) with controllable thickness. This novel nanocomposite was characterized by TEM, FTIR, XRD, XPS, N2 adsorption–desorption isotherms, and VSM. The prepared Fe3O4@PDA-Pd@[Cu3(btc)2] (n=5) nanocomposite shows ultrahigh catalytic activity for the 4-nitrophenol reduction and Suzuki–Miyaura coupling reactions of aryl halides (Br, Cl) with arylboronic acids. Moreover, the nanocomposite also can be easily separated by an external magnet and reused at least 8 runs with excellent yields for both the reactions. The catalyst has outstanding catalytic performance, mainly because the integration of [Cu3(btc)2] with Fe3O4@PDA-Pd that combines the advantages of each component could exhibit a synergistic effect in the catalytic system.

Palladium Supported on Metformin-Functionalized Magnetic Polymer Nanocomposites: A Highly Efficient and Reusable Catalyst for the Suzuki–Miyaura Coupling Reaction

In this paper, a novel magnetically responsive nanocatalyst, Pd/Fe3O4@PMAA-Met (PMAA=poly(methacrylic acid), Met=metformin), has been successfully prepared by immobilizing palladium on the surface of metformin-functionalized magnetic polymer nanocomposites. This novel nanocatalyst was characterized by FTIR, XRD, TEM, X-ray photoelectron spectroscopy (XPS), and vibrating sample magnetometry (VSM). The prepared nanocatalyst showed excellent catalytic activity for Suzuki–Miyaura coupling reactions of aryl halides (I, Br, Cl) with arylboronic acids even at palladium loadings of 0.01–0.0007 mol % and the turnover frequency (TOF) reached up to 125 714 h?1. The excellent activity of this Pd/Fe3O4@PMAA-Met catalyst could be attributed to a “release and catch” catalytic mechanism as well as its nanometer size. This nanocatalyst could be simply separated with an external magnet and reused at least twelve times with excellent yields achieved.

Excellent Suzuki–Miyaura catalytic activity of a new Pd(II) complex with sulfonamide–Schiff base ligand

A new air-stable Pd(II) complex containing a sulfonamide–Schiff base ligand has been synthesized, characterized and investigated as a catalyst for the Suzuki–Miyaura reactions of aryl halides with arylboronic acids. Theoretical calculations (B3LYP) and spectroscopic evidence suggest that the sulfonamide–Schiff base coordinates to the Pd centre through sulfonamide nitrogen (?SO2NH2) rather than imine (?CH?N). The complex shows excellent cross-coupling activity with aryl bromides in water at room temperature and aryl chlorides in isopropanol at 60°C. Copyright

Phosphine-stabilized Pd nanoparticles supported on silica as a highly active catalyst for the Suzuki-Miyaura cross-coupling reaction

We have prepared a silica supported palladium nanocatalyst (PdNP@PPh2-SiO2) with high dispersion via a one-step reaction between commercially available 2-diphenylphosphinoethyl-functionalized silica gel (PPh2-SiO2) and PdCl2 without the assistance of an external reductant or stabilizer. The catalyst was well characterized by N2-adsorption, XRD, HRTEM, SEM-EDX and ICP analyses. The supported catalyst exhibited excellent activity for the Suzuki-Miyaura cross-coupling reactions of aryl halides (including aryl chlorides) with arylboronic acids. The facile synthesis of the catalyst combined with high product yields at relatively low catalyst loading (0.5 mol%) represents one of the most efficient silica supported heterogeneous systems for the Suzuki coupling of aryl chlorides. The catalyst could be reused several times without compromising its activity.

A highly efficient Schiff-base derived palladium catalyst for the Suzuki-Miyaura reactions of aryl chlorides

A new palladium complex derived from a bidentate Schiff-base ligand showed excellent activity as catalyst for the Suzuki-Miyaura cross-coupling reactions of less reactive aryl chlorides with arylboronic acids. Under an optimized condition, moderate-to-excellent yields of biaryls were obtained with a wide range of substrates at a relatively low loading of catalyst (0.2 mol %).

Suzuki-Miyaura coupling of aryl iodides, bromides, and chlorides catalyzed by bis(thiazole) pincer palladium complexes

Bis(thiazole) pincer palladium complexes showed efficient catalytic activity for the Suzuki-Miyaura coupling of aryl halides, allowing the synthesis of biaryls with very high turnover numbers and turnover frequencies. The complexes were successfully applied in the scalable and green synthesis of the key intermediates of bioactive LUF5771 and its analogues.