4433-13-0

Basic information

• Product Name: 4,4'-Divinylbiphenyl
• Synonyms: 4,4'-Divinylbiphenyl;4,4-Divinyl-p-biphenyl;4,4'-Diethenyl-1,1'-biphenyl
• CAS NO: 4433-13-0
• Molecular Formula: C₁₆H₁₄
• Molecular Weight: 206.28236
• Mol File: 4433-13-0.mol
• Article Data: 24

Chemical Properties

• Melting Point: 153 °C(Solv: water (7732-18-5); ethanol (64-17-5))
• Boiling Point: 341.6±22.0 °C(Predicted)
• Appearance: /
• Density: 0.998±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 4,4'-Divinylbiphenyl(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-Divinylbiphenyl(4433-13-0)
• EPA Substance Registry System: 4,4'-Divinylbiphenyl(4433-13-0)

Safety Data

• Hazardous Substances Data: 4433-13-0(Hazardous Substances Data)

Usage

Preparation

The preparation of 4,4'-Divinylbiphenyl is as follows:?Reaction flask (10 mL) equipped with stirring bar was charged with 4-vinylphenylboronic acid (135mg, 0.91 mmol), ethanol (96%) (2 mL), [{Pd(μ-OH)Cl(IPr)}2] (510-4 g, 4.55 × 10-7 mol). Reactionmixture was stirred at 22 C for 6 h. After completion of the reaction solvent was evaporated, theresidue was dissolved in hexane (5 mL) and extracted with water (2 × 2 mL). The organic layer wasdried over magnesium sulphate, and hexane was evaporated under reduced pressure. 176 mg of 4,4'-divinylbiphenyl was obtained as a white solid. Yield = 93%.

Upstream product

• 2039-82-9 1-bromo-4-ethenyl-benzene 
• 15480-49-6 α,α'-dimethyl-4,4'-biphenylenedimethanol 
• 79-41-4 poly(methacrylic acid) 
• 92-86-4 4-(4-bromophenyl)bromobenzene 
• 108-86-1 bromobenzene 
• 2156-04-9 4-Vinylphenylboronic acid 
• 106-41-2 4-bromo-phenol 
• 83813-73-4 vinyl 4-methylbenzenesulfonate 
• 5487-93-4 4,4'-biphenyldiboronic acid bis(neopentyl glycol) cyclic ester 
• 38215-38-2 4,4'-diethynylbiphenyl 
• 103-83-3 N,N'-dimethylbenzylamine 
• 2351-37-3 4,4'-biphenyldicarboxylic acid dichloride 
• 209738-38-5 4-vinyl-4'-α-hydroxyethyl-biphenyl 
• 112-49-2 Triethylene glycol dimethyl ether 

Downstream Products

• 1198573-83-9 dimethyl 2,2'-(biphenyl-4,4'-diyl)bis(1-(pyrrolidin-1-ylcarbonyl)cyclopropanecarboxylate) 

Relevant articles and documents

Supported gold catalyzes the homocoupling of phenylboronic acid with high conversion and selectivity

(Chemical Equation Presented) Gold on nanocrystalline cerium oxide is a highly active and selective catalyst for the homocoupling of phenylboronic acid derivatives in the presence of K2CO3 as a base (see picture). Au3+ species are thought to be the active sites for the reaction, and water is required to activate the boronic acid through the participation of surface hydroxy groups.

"benchtop" Biaryl Coupling Using Pd/Cu Cocatalysis: Application to the Synthesis of Conjugated Polymers

Typically, Suzuki couplings used in polymerizations are performed at raised temperatures in inert atmospheres. As a result, the synthesis of aromatic materials that utilize this chemistry often demands expensive and specialized equipment on an industrial scale. Herein, we describe a bimetallic methodology that exploits the distinct reactivities of palladium and copper to perform high yielding aryl-aryl dimerizations and polymerizations that can be performed on a benchtop under ambient conditions. These couplings are facile and can be performed by simple mixing in the open vessel. To demonstrate the utility of this method in the context of polymer synthesis: polyfluorene, polycarbazole, polysilafluorene, and poly(6,12-dihydro-dithienoindacenodithiophene) were created at ambient temperature and open to air.

Efficient Homocoupling of Aryl- and Alkenylboronic Acids in the Presence of Low Loadings of [{Pd(μ-OH)Cl(IPr)} 2 ]

NHC-palladium(II) complex [{Pd(μ-OH)Cl(IPr)} 2 ] (IPr = bis(2,6-diisopropylphenyl)imidazolin-2-ylidene) catalyzes the oxidative coupling of a broad spectrum of aryl- and alkenylboronic acids at loadings down to 5 ppm. At the concentration of 0.05 mol% the catalyst permits an efficient reaction under base-free conditions.

Ligand-, base-, co-catalyst-free copper fluorapatite (CuFAP) as a versatile, ecofriendly, heterogeneous and reusable catalyst for an efficient homocoupling of arylboronic acid at ambient reaction conditions

This paper describes the first report in which copper species containing copper fluorapatite (CuFAP) acts as a versatile, eco-friendly, recyclable, heterogeneous catalyst for an efficient synthesis of symmetric biaryls from the homo-coupling of arylboronic acids in methanol solvent at ambient reaction conditions. The developed protocol is ligand-, base-, and co-catalyst-free, sustainable, mild, inexpensive, and compatible with a wide range of aromatic/heterocyclic boronic acids and provides the corresponding products in excellent yields without purification. The catalyst was easily recovered from the reaction mixture and reused several times without loss of activity.