94363-13-0

Basic information

• Product Name: 1,4-diphenylbenzene
• CAS NO: 94363-13-0
• Molecular Formula: C18H14
• Molecular Weight: 230.3
• Mol File: 94363-13-0.mol
• Article Data: 462

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,4-diphenylbenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-diphenylbenzene(94363-13-0)
• EPA Substance Registry System: 1,4-diphenylbenzene(94363-13-0)

Safety Data

• Hazardous Substances Data: 94363-13-0(Hazardous Substances Data)

Usage

Chemical structure

Three benzene rings linked together by carbon-carbon bonds

Physical state

White crystalline solid

Solubility

Insoluble in water

Industrial use

High-temperature solvent and heat-transfer fluid

Synthesis

Precursor in the synthesis of various organic compounds

Stability

Relatively stable

Reactivity

Low reactivity

Applications

Wide range of applications in the chemical and industrial sectors

Safety concerns

Potential health hazards and environmental impact; should be handled with care

Upstream product

• 110-89-4 piperidine 
• 60-29-7 diethyl ether 
• 591-51-5 phenyllithium 
• 2051-62-9 4'-biphenyl chloride 
• 92-52-4 biphenyl 
• 2396-01-2 phenyl radical 
• 100-34-5 benzene diazonium chloride 
• 99-99-0 1-methyl-4-nitrobenzene 
• 84-15-1 o-terphenyl 
• 519-67-5 2,5-dihydroxy-3,6-bis(4-hydroxyphenyl)cyclohexa-2,5-diene-1,4-dione 
• 799764-69-5 4-bromo-4′-cyclohexylbiphenyl 
• 56-23-5 tetrachloromethane 
• 5452-64-2 4-cyclohex-1-enyl-biphenyl 
• 118-75-2 chloranil 

Downstream Products

• 13478-57-4 1-terphenyl-4-yl-3-phenylbenzene 
• 102948-86-7 4'-biphenyl-4-yl-2-methyl-benzophenone 
• 105541-30-8 4,4''-Di-o-toluoyl-p-terphenyl 
• 14739-51-6 [1,1';4',1'';3'',1''';4''',1'''';4'''',1''''']Sexiphenyl 
• 38116-50-6 1,4-Dihydro-1-methyl-p-terphenyl 
• 38116-52-8 trans-1',4'-Dihydro-1',4'-dimethyl-p-terphenyl 
• 38116-51-7 cis-1',4'-Dihydro-1',4'-dimethyl-p-terphenyl 
• 3073-05-0 penta-p-phenylene 
• 854749-71-6 4,4''-bis-(α-chloro-benzhydryl)-p-terphenyl 
• 857545-87-0 4,4''-Bis-(α-hydroxy-benzhydryl)-p-terphenyl 
• 17802-72-1 Diphenyl-p-terphenyl-4-yl-methanol 

Relevant articles and documents

C2-Symmetric normal and mesoionic bis-N-heterocyclic carbenes with biphenyl backbone. A comparison of bis(1,2,3-triazol-5-ylidene) and bis(imidazol-2-ylidene) ligands

C2-Symmetric normal and mesoionic bis-N-heterocyclic carbenes (NHCs) derived from 1,1′-((1,1′-biphenyl)-2,2′- diylbis(methylene))bis(3-methyl-4-phenyl-1H-1,2,3-triazol-3-ium) diiodide (5) and 3,3′-((1,1′-biphenyl)-2,2′-diylbis(methylene))bis(1- phenyl-1H-imidazol-3-ium) dibromide (6) were used as ligands for the synthesis of the corresponding Pd(II) complexes. 2,2′-Disubstituted 1,1′-biphenyl moiety was used as the C2-symmetric backbone for the synthesis. 2,2′-Bis(bromomethyl)-1,1′-biphenyl was used as a common precursor for the synthesis of both 5 and 6. These salts were treated with Ag2O for the in-situ generation of the corresponding NHC-Ag(I) complexes which were transmetallated to the corresponding Pd(II) chloro and acetate complexes. The bis(1,2,3-triazol-5-ylidene) derivative gave structurally well-defined mono nuclear chelate complexes that were characterized by spectroscopic and single crystal XRD data. The bis(imidazol-3-ylidene) derivative gave polymeric complex and not the expected mono nuclear chelate complex. These complexes were compared for their reactivity in Suzuki-Miyaura coupling reaction.

Nickel-Catalyzed Direct Cross-Coupling of Aryl Sulfonium Salt with Aryl Bromide

The direct cross-couplings of aryl sulfonium salts with aryl halides could be achieved by using nickel as a reaction catalyst. The reactions proceeded efficiently via C-S bond activation in the presence of magnesium turnings and lithium chloride in THF at ambient temperature to afford the corresponding biaryls in moderate to good yields, potentially serving as an attractive alternative to conventional cross-coupling reactions employing preprepared organometallic reagents.

Suzuki cross-coupling of hexachlorobenzene promoted by the Buchwald ligands

The study of cross-coupling between hexachlorobenzene and phenylboronic acid comprised five Buchwald ligands, from which 2-dicyclohexylphosphino-2′-(dimethylamino)biphenyl (DavePHOS) provided the best conversion. When excess of phenylboronic acid was used, a mixture of isomeric tri-, tetra- and pentaphenyl-substituted derivatives in the ～10:70:20 ratio was obtained, along with minor amounts of hydrodechlorination products.