189828-30-6

Basic information

• Product Name: 2'-Methyl-[1,1'-Biphenyl]-4-Carbonitrile
• Synonyms: [1,1'-Biphenyl]-4-carbonitrile,2'-methyl-;4-(2-Methylphenyl)benzonitrile;2'-Methylbiphenyl-4-carbonitrile;4-Cyano-2'-methylbiphenyl
• CAS NO: 189828-30-6
• Molecular Formula: C₁₄H₁₁N
• Molecular Weight: 193.24
• Mol File: 189828-30-6.mol
• Article Data: 58

Chemical Properties

• Melting Point: 54-56℃ (hexane ethyl acetate )
• Boiling Point: 327 °C at 760 mmHg
• Flash Point: 152.2 °C
• Appearance: /
• Density: 1.09 g/cm³
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2'-Methyl-[1,1'-Biphenyl]-4-Carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-Methyl-[1,1'-Biphenyl]-4-Carbonitrile(189828-30-6)
• EPA Substance Registry System: 2'-Methyl-[1,1'-Biphenyl]-4-Carbonitrile(189828-30-6)

Safety Data

• Hazardous Substances Data: 189828-30-6(Hazardous Substances Data)

Usage

Uses

4-(2-Methylphenyl)benzonitrile is a useful chemical in organic synthesis.

Upstream product

• 623-00-7 4-bromobenzenecarbonitrile 
• 623-03-0 4-Cyanochlorobenzene 
• 95-49-8 2-methylchlorobenzene 
• 171364-82-2 4-cyanophenylboronic acid pinacol ester 
• 16419-60-6 2-Methylphenylboronic acid 
• 767-00-0 4-cyanophenol 
• 33719-37-8 4-cyanobenzene-1-sulfonyl fluoride 
• 49584-26-1 p-cyanobenzenesulfonyl chloride 
• 30432-34-9 tri-o-tolylaluminum 
• 6699-93-0 (2-methylphenyl)lithium 
• 3058-39-7 4-iodobenzonitrile 
• 7029-31-4 bis(2-methylphenyl)zinc 
• 118-90-1 ortho-methylbenzoic acid 
• 84109-17-1 2-methylphenylzinc chloride 

Downstream Products

• 544694-59-9 4-{4-[(4'-carbamimidoyl-biphenyl-2-ylmethyl)-methanesulfonyl-amino]-phenoxy}-piperidine-1-carboxylic acid tert-butyl ester 
• 146534-79-4 2'-bromomethyl-biphenyl-4-carbonitrile 

Relevant articles and documents

Synthesis and application of N-heterocyclic carbene-palladium ligands with glycerol dendrons for the Suzuki-Miyaura cross-coupling in water

Highly active glycerol-dendron-supported N-heterocyclic carbene-palladium catalysts with catalytic sites at the core position were obtained with an efficient modular synthesis. A symmetrical ligand structure was designed to build a larger microenvironment by increasing the number of dendron generations. The catalytic activity was tested in Suzuki-Miyaura cross-coupling reactions. Deprotection of the dendritic supported catalysts allowed the catalytic reaction to take place in neat water, which is highly desirable for a more sustainable processing. A positive dendritic effect was observed for coupling of activated and nonactivated bromoaryls. Georg Thieme Verlag Stuttgart. New York.

Palladium-catalyzed borylation of aryl bromides and chlorides using phosphatrioxa-adamantane ligands

Catalysts based on the combination of Pd(OAc)2 and the electron-deficient phosphatrioxa-adamantane ligands are described for borylation of aryl bromides and chlorides. Catalytic evaluation of a small library of phosphatrioxa-adamantane ligands provided some insights on the preferred ligand steric profile for borylation reactions. The corresponding aryl boronate esters were accessed under mild conditions (25–70 °C) and isolated in high yields (up to 96%).

Method for preparing biaryl hydrocarbon compound by Suzuki coupling reaction

The invention discloses a preparation method of a biaryl hydrocarbon compound as shown in a structural formula III (the structural formula and substituent are shown in the specification), which comprises the following steps: adding a nonionic surfactant into a reaction system, and carrying out Suzuki coupling reaction on chlorinated aromatic hydrocarbon as shown in a structural formula I and arylboronic acid as shown in a structural formula II. The preparation method provided by the invention is high in chlorinated aromatic hydrocarbon reaction activity, low in raw material cost, mild in reaction condition, green and environment-friendly.

Suzuki-Miyaura coupling catalyzed by a Ni(II) PNP pincer complex: Scope and mechanistic insights

The nickel(II) pincer complex, [NiCl(PhPNP)] (PhPNP = anion of 2,5-bis(diphenylphosphinomethyl)pyrrole), has been employed as a precatalyst for the Suzuki-Miyaura cross-coupling reaction of aryl halides and boronic acids. Both electron-rich and electron-deficient aromatic bromides were found to undergo coupling with boronic acids in modest yield at elevated temperature in the presence of K3PO4·H2O. Preliminary mechanistic studies of the reaction identified a novel species formulated as the boronate complex, [Ni(OB{OH}{2-tolyl})(PhPNP)], which most likely represents a catalyst deactivation pathway. The productive catalytic cycle was found to be most consistent with a Ni(I)/Ni(III) process where the boronic acid serves as both reductant and nucleophile in the presence of base.