27104-67-2

Basic information

• Product Name: 2-Biphenylcarbonitrile
• Synonyms: 4'-(Dimethylamino)-[1,1'-biphenyl]-2-carbonitrile
• CAS NO: 27104-67-2
• Molecular Formula: C13H9N
• Molecular Weight: 179
• Mol File: 27104-67-2.mol
• Article Data: 3

Chemical Properties

• Melting Point: 106-107℃ (ligroine ethyl acetate )
• Boiling Point: 403.9 °C at 760 mmHg
• Flash Point: 179.8 °C
• Appearance: /
• Density: 1.11 g/cm³
• PKA: 4.32±0.12(Predicted)
• CAS DataBase Reference: 2-Biphenylcarbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Biphenylcarbonitrile(27104-67-2)
• EPA Substance Registry System: 2-Biphenylcarbonitrile(27104-67-2)

Safety Data

• Hazardous Substances Data: 27104-67-2(Hazardous Substances Data)

Usage

General Description

2-Biphenylcarbonitrile, also known as o-phenylbenzonitrile, is a chemical compound with the formula C13H9N. It is a white solid at room temperature and is insoluble in water. This chemical is often used as a building block in the synthesis of various organic compounds and pharmaceuticals. It is also employed in the preparation of liquid crystals, dyes, and optical brighteners. 2-Biphenylcarbonitrile is considered to be a hazardous chemical with potential health hazards and should be handled with proper safety precautions in a controlled laboratory environment.

Upstream product

• 2042-37-7 o-cyanobromobenzene 
• 698-69-1 4-chloro-N,N-dimethylaniline 
• 108949-55-9 4-N,N-dimethylaminophenyl magnesium chloride 
• 171364-78-6 (4-(N,N-dimethylamino)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Relevant articles and documents

[Pd(Cl)2(P(NC5H10)(C6H 11)2)2] - A highly effective and extremely versatile palladium-based negishi catalyst that efficiently and reliably operates at low catalyst loadings

[Pd(Cl)2(P(NC5H10)-(C6H 11)2]2] (1) has been prepared in quantitative yield by reacting commercially available [Pd(cod)(Cl)2] (cod = cyclooctadiene) with readily prepared 1-(dicyclohexylphosphanyl)piperidine in toluene under N2 within a few minutes at room temperature. Complex 1 has proved to be an excellent Negishi catalyst, capable of quantitatively coupling a wide variety of electronically activated, non-activated, deactivated, sterically hindered, heterocyclic, and functionalized aryl bromides with various (also heterocyclic) arylzinc reagents, typically within a few minutes at 100°C in the presence of just 0.01 mol% of catalyst. Aryl bromides containing nitro, nitrile, ether, ester, hydroxy, carbonyl, and carboxyl groups, as well as acetais, lactones, amides, anilines, alkenes, carboxylic acids, acetic acids, and pyridines and pyrimidines, have been successfully used as coupling partners. Furthermore, electronic and steric variations are tolerated in both reaction partners. Experimental observations strongly indicate that a molecular mechanism is operative.

Palladium-catalyzed borylation of phenyl bromides and application in one-pot Suzuki-Miyaura biphenyl synthesis

(Chemical equation presented) The coupling reaction of pinacolborane with various aryl bromides in the presence of a catalytic amount of Pd(OAc) 2 together with DPEphos as ligand and Et3N as base provided arylboronates. High yields were obtained in the case of electron-donor substituted aryl bromides. The direct preparation of arylboronates allowed the one-pot, two-step synthesis of unsymmetrical biaryls in high yields.