58743-77-4

Usage

Uses

Used in Pharmaceutical Industry:
4'-methoxy[1,1'-biphenyl]-4-carbonitrile is used as an intermediate in the synthesis of pharmaceutical compounds for its potential medicinal properties. It serves as a valuable building block in drug discovery and development, contributing to the creation of new therapeutic agents.
Used in Materials Science:
In the field of materials science, 4'-methoxy[1,1'-biphenyl]-4-carbonitrile is utilized in the development of organic electronic materials. Its unique electronic and physical properties make it suitable for use in organic semiconductor devices, enhancing their performance and expanding their applications.

Upstream product

• 623-00-7 4-bromobenzenecarbonitrile 
• 93296-09-4 4-methoxyphenylzinc chloride 
• 3058-39-7 4-iodobenzonitrile 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 66107-32-2 4-cyanophenyl trifluoromethanesulfonate 
• 171364-79-7 2-(4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 696-62-8 para-iodoanisole 
• 623-12-1 4-chloromethoxybenzene 
• 126747-14-6 4-cyanophenylboronic acid 
• 5720-07-0 4-methoxyphenylboronic acid 
• 127783-75-9 4'-cyano-[1,1'-biphenyl]-4-yl acetate 
• 19812-93-2 4-Cyano-4'-hydroxybiphenyl 
• 74-88-4 methyl iodide 
• 108-77-0 1,3,5-trichloro-2,4,6-triazine 

Downstream Products

• 613-37-6 4-methoxylbiphenyl 
• 1332363-01-5 4-methoxy-4'-deutero-1,1'-biphenyl 
• 19812-93-2 4-Cyano-4'-hydroxybiphenyl 
• 52364-73-5 4-octyloxy-4'-cyanobiphenyl 
• 59748-18-4 4'-octyloxy(1,1'-biphenyl)-4-carboxylic acid 

Relevant academic research and scientific papers

Preparation, structure and catalytic properties of a binuclear Pd(0) complex with bridging silylene ligands

In contrast to the N-heterocyclic carbene (NHC) 1, the homologous N-heterocyclic silylene (NHS) 4 acts as a bridging ligand to Pd(0), giving rise to the dinuclear complex 5 which is catalytically active in Suzuki reactions.

Preparation and characterization of Cu based on 2-(5-Aminopyrimidin-2-yl)pyrimidin-5-amine as novel recyclable metal–organic frameworks for Suzuki reaction

For first time, in this work, a new, heterogeneous and recyclable catalyst was designed using immobilizing Cu on 2-(5-Aminopyrimidin-2-yl)pyrimidin-5-amine ([CuAPPA·2H2O]n) named metal–organic frameworks (MOFs). This catalyst was used for the synthesis of biaryl derivatives by Suzuki reaction. Suzuki reaction performed with mixing of the aryl halides with arylboronic acids in the DMF solvent conditions. Also, the prepared catalyst was characterized with different analytical techniques such as FT-IR, XRD, SEM, EDX, BET and ICP-AES analysis. [CuAPPA·2H2O]n catalyst displayed good to excellent yields catalytic efficiency for Suzuki reaction in comparison with to other catalysts. Also, the recoverability and reusability related to this catalyst was checked by a simple filtration with reserving its activity even after several cycles.

'Awaken' aryl sulfonyl fluoride: a new partner in the Suzuki-Miyaura coupling reaction

An example of the activation of the -SO2F group, which is traditionally considered a stable group even in the presence of a transition metal, is described using a novel partner in the Suzuki-Miyaura coupling reaction catalyzed by Pd(OAc)2 and Ruphos as ligands. The products showed good to outstanding yields and broad functional group compatibility under optimal conditions. The sequential synthesis of non-symmetric terphenyls and the gram grade process highlight the approach's synthetic utility. DFT calculations have shown that Pd0 prefers to insert between C-S bonds rather than S-F bonds. This journal is

Biaryl Coupling of Aryldiazonium Salts and Arylboronic Acids Catalysed by Gold

A gold-catalysed coupling of aryldiazonium salts with arylboronic acids is described. The reactions proceed in satisfactory yields under irradiation with blue LEDs in the presence of KF and a catalytic amount of ascorbic acid. Notably, 4-nitrobenzendiazonium tetrafluoroborate is sufficiently reactive to undergo the coupling with a variety of arylboronic acids in the absence of aryl radical initiators. The coupling is applicable for electron-donating and electron-withdrawing groups present at the para, ortho, and meta positions of both substrates.

Pd Nanoparticles Embedded Into MOF-808: Synthesis, Structural Characteristics, and Catalyst Properties for the Suzuki–Miyaura Coupling Reaction

Abstract: A heterogeneous single-site catalyst Pd@MOF-808 was successfully synthesized by water-based, green synthesis procedure. The catalytic experiments exhibited the Pd@MOF-808 promoted efficiently the Suzuki–Miyaura coupling reaction without the assistance of organic phosphine ligands at atmospheric pressure conditions. The catalyst also could be applied in the gram-scale synthesis of industrially anti-inflanmatory analgestic Fenbufen. Graphic Abstract: [Figure not available: see fulltext.]

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.

Complexes LNi(Cp)X with alkylamino-substituted N-heterocyclic carbene ligands (L) and their catalytic activity in the Suzuki—Miyaura reaction

New nickel(ii) complexes of the general formula LNi(Cp)X (L is an N-heterocyclic carbene (NHC) ligand of the 1,2,4-triazole or imidazole series; Cp is the cyclopentadienyl anion; X = Cl, I) are reported. In these complexes, the NHC ligands (L) contain an alkylamino group at the 3 or 4 position of the heterocycle. The synthesized complexes and structurally similar complexes without an alkylamino group were tested for catalytic activity in the Suzuki—Miyaura reaction. The introduction of an alkylamino group into the NHC ligand leads to the enhancement of the catalytic activity of complexes with N,N′-diaryl-substituted NHC ligands of the imidazole series and a decrease in the activity of the complexes with N,N′-dialkyl-substituted NHC ligands of the 1,2,4-triazole series.

A comparative study of catalytic activity on iron-based carbon nanostructured catalysts with Pd loading: Using the Box–Behnken design (BBD) method in the Suzuki–Miyaura coupling

Highly dispersed palladium nanoparticles immobilized on surface-modified Fe3O4 NPs and magnetic carbon nanostructures (CNSs; carbon nanotubes/graphene oxide) were synthesized and applied as a recyclable and reusable nanocatalyst to achieve palladium (II)-catalyzed Suzuki–Miyaura reaction of arylboronic acid with aryl bromides. Carbon nanostructures with immobilized hydantoin (PH)-Pd complex display excellent stability, including a high performance at low catalyst loading. Magnetic separation prevents catalyst centrifuge or filtration and also contributes to practical techniques for recovery. Next, a response surface method based on a three-level Box–Behnken design was used, which involved three factors: catalyst loading, reaction time, and solvent. The Box–Behnken method was advantageous to parameters optimization for obtaining a yield, with high efficiency and accuracy. As a result of catalytic tests, the TONs and TOFs were calculated from all coupling reactions. The prepared nano-magnetic catalysts, after the catalysis reaction, can be easily recovered through the magnetic field. Evaluated catalytic performance indicates that these types of catalysts can function as effective recyclable catalysts at least five times without losing the initial level of catalytic activity.

Preparation of Functionalized Diorganomagnesium Reagents in Toluene via Bromine or Iodine/Magnesium-Exchange Reactions

A wide range of polyfunctionalized di(hetero)aryl- and dialkenyl-magnesium reagents are prepared in toluene within 10 to 120 minutes between 78 C and 25 C via an I/Mg- or Br/Mg-exchange reaction using reagents of the general formula R2Mg (R = sBu, Mes). Highly sensitive functional groups, such as triazene or nitro, are tolerated in these exchange reactions, enabling the synthesis of various functionalized (hetero)arene and alkene derivatives after quenching with several electrophiles including allyl bromides, acyl chlorides, aldehydes, ketones, and aryl iodides.

Heterogeneous Fe3O4@Si–NHC–Pd Catalyst: Synthesis, Characterization, and Catalytic Activity in the Suzuki–Miyaura Cross-Coupling Reaction under Mild Conditions

Abstract: A novel Fe3O4@Si–NHC–Pd catalystwith N-heterocyclic carbenes (NHCs) moiety as an alternative ligand tophosphines for metal complexes has been synthesized and characterized by variousmethods. Synthesis of metal nanoparticles has been accomplished withoutaggregation, and the prepared catalyst has been applied in theSuzuki–Miyauracross-coupling reaction of boronic acids and aryl halides in water usingEt3N as a base. The catalyst has demonstrated highefficiency at room temperature and can be easily removed from the reaction mediausing an external magnetic field and recycled at least five times withoutsignificant decrease of its activity.