57774-36-4

Basic information

• Product Name: 4'-Chloro-4-cyanobiphenyl
• Synonyms: 4'-chloro-4-cyanobiphenyl;4-(4-Chlorophenyl)benzonitrile
• CAS NO: 57774-36-4
• Molecular Formula: C₁₃H₈ClN
• Molecular Weight: 213.66
• Mol File: 57774-36-4.mol
• Article Data: 8

Chemical Properties

• Melting Point: 129-130 °C
• Boiling Point: 359.8 °C at 760 mmHg
• Flash Point: 156.4 °C
• Appearance: /
• Density: 1.24 g/cm³
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4'-Chloro-4-cyanobiphenyl(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-Chloro-4-cyanobiphenyl(57774-36-4)
• EPA Substance Registry System: 4'-Chloro-4-cyanobiphenyl(57774-36-4)

Safety Data

• Hazardous Substances Data: 57774-36-4(Hazardous Substances Data)

Usage

General Description

4'-Chloro-4-cyanobiphenyl, also known as PCB-3, is a chemical compound belonging to the biphenyl class of organic compounds. It is a cyanobiphenyl derivative that is used as a liquid crystal material and an intermediate for the synthesis of liquid crystal compounds. It has a molecular formula of C12H8ClN and a molecular weight of 203.7 g/mol. 4'-Chloro-4-cyanobiphenyl is considered to be a persistent organic pollutant and is listed under the Stockholm Convention on Persistent Organic Pollutants. It is important to handle this chemical with caution as it is toxic to aquatic life and can have harmful effects on human health, including being a possible carcinogen.

Upstream product

• 637-87-6 1-Chloro-4-iodobenzene 
• 58666-77-6 (4-cyanophenyl)trimethylstannane 
• 2863-98-1 4-hydrazinobenzonitrile hydrochloride 
• 1073-70-7 4-chlorophenylhydrazine hydrochloride 
• 3058-39-7 4-iodobenzonitrile 
• 28034-99-3 4'-Chloro-4-biphenylol 
• 100-47-0 benzonitrile 
• 62-53-3 aniline 
• 623-00-7 4-bromobenzenecarbonitrile 
• 673-41-6 p-chlorobenzenediazonium tetrafluoroborate 

Downstream Products

• 1334717-21-3 6-chloro-N-{(4'-chloro-[1,1'-biphenyl]-4-yl)methyl}-2-ethylimidazo[1,2-a]pyridine-3-carboxamide 
• 1334717-33-7 7-chloro-N-{(4′-chloro-[1,1′-biphenyl]-4-yl)methyl}-2-ethylimidazo[1,2-a]pyridine-3-carboxamide 
• 15996-82-4 (4'-chloro-[1,1'-biphenyl]-4-yl)methanamine 
• 5748-41-4 4'-chlorobiphenyl-4-carboxylic acid 

Relevant articles and documents

Ligand-free palladium catalyzed Ullmann biaryl synthesis: 'Household' reagents and mild reaction conditions

A palladium catalysed Ullmann biaryl synthesis has been developed using hydrazine hydrate as the reducing reagent at room temperature. The combination of Pd(OAc)2 and hydrazine hydrate works smoothly for the coupling of both electron-rich and electron-deficient aryl iodides, as well as hetero-aryl iodides, leading to a wide range of biaryls in good to excellent yields. The reaction requires only 1 mol% Pd(OAc)2 and the in situ generated palladium naoparticles are found to be active catalysts.

Strongly Directing Substituents in the Radical Arylation of Substituted Benzenes

Although general interest in radical arylation reactions has grown rapidly in recent years, poor regioselectivities and the need to use a large excess of the radical-accepting arene have hindered their application to substituted benzenes. We now describe experimental and computational investigations into the substituent effects that lead to regioselective addition based on the recent discovery of anilines as outstanding substrates for radical arylations.

Structure-reactivity relationships in negishi cross-coupling reactions

Competition experiments have been performed to determine the relative reactivities of substituted bromobenzenes and of different arylzinc reagents in the [Pd(PPh3)4]-catalyzed Negishi cross-coupling reaction in THF at 25 °C. The crosscoupling reactions are accelerated by electron acceptors in the bromobenzenes, the effect of which increases in the order ortho a larger effect than substituent variations in the arylzinc halides (ρ = -0.98).