21175-18-8

Basic information

• Product Name: 4-[(E)-2-phenylethenyl]biphenyl
• CAS NO: 21175-18-8
• Molecular Formula: C₂₀H₁₆
• Molecular Weight: 256.341
• Mol File: 21175-18-8.mol
• Article Data: 69

Chemical Properties

• Boiling Point: 412.4°C at 760 mmHg
• Flash Point: 197.3°C
• Density: 1.077g/cm³
• Vapor Pressure: 1.24E-06mmHg at 25°C
• Refractive Index: 1.663
• CAS DataBase Reference: 4-[(E)-2-phenylethenyl]biphenyl(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[(E)-2-phenylethenyl]biphenyl(21175-18-8)
• EPA Substance Registry System: 4-[(E)-2-phenylethenyl]biphenyl(21175-18-8)

Safety Data

• Hazardous Substances Data: 21175-18-8(Hazardous Substances Data)

Upstream product

• 3218-36-8 4-Phenylbenzaldehyde 
• 126472-66-0 (benzyl)(phenyl)phosphinic fluoride 
• 56181-61-4 4-(1-bromo-2-phenylethyl)-1,1'-biphenyl 
• 1449-46-3 benzyltriphenylphosphonium bromide 
• 1122-91-4 4-bromo-benzaldehyde 
• 98-80-6 phenylboronic acid 
• 2001-23-2 1-(biphenyl-4-yl)-2-phenylethanone 
• 31233-64-4 1-biphenyl-4-yl-2-phenyl-ethanol 
• 1657-49-4 1-chloro-4-styrylbenzene 
• 100-59-4 phenylmagnesium chloride 
• 100-42-5 styrene 
• 92-66-0 4-bromo-1,1'-biphenyl 
• 4714-24-3 1-bromo-4-styrylbenzene 
• 100-52-7 benzaldehyde 

Downstream Products

• 14310-35-1 4-phenethyl-1,1′-biphenyl 
• 2039-69-2 (Z)-4-styryl-1,1'-biphenyl 

Relevant articles and documents

Pd-Catalyzed Cross-Coupling of Organostibines with Styrenes to Give Unsymmetric (E)-Stilbenes and (1 E,3 E)-1,4-Diarylbuta-1,3-dienes and Fluorescence Properties of the Products

A general and effective palladium-catalyzed cross-coupling of organostibines with styrenes to give (E)-olefins was disclosed. By the use of an organostibine reagent, this method can produce unsymmetric (E)-1,2-diarylethylenes and (1E,3E)-1,4-diarylbuta-1,3-dienes in good yields with high E/Z selectivity and good functional group tolerance. Resveratrol and DMU-212 were synthesized in high yield. The protocol can be extended to the synthesis of (1E,3E,5E)-1,6-diphenylhexa-1,3,5-triene in 40% yield. Products 5e, 5f, and 7a showed good photoluminescence quantum yields ranging from 72 to 99%.

Mizoroki-Heck Reaction of Unstrained Aryl Ketones via Ligand-Promoted C-C Bond Olefination

Mizoroki-Heck reaction of unstrained aryl ketone with acrylate/styrene is accomplished via palladium-catalyzed ligand-promoted C-C bond cleavage. Various (hetero)aryl ketones are compatible in the reaction, affording the alkene product in good to excellent yields. Further applications in the late-stage olefination of some drugs, natural products, and fragrance-derived aryl ketones demonstrate the synthetic utility of this protocol. By employing ketone as both the directing group and the leaving group, 1,2-bifunctionalization is achieved via sequential ortho-C-H alkylation/ipso-Heck olefination.

Bimetallic Ni–Pd Synergism—Mixed Metal Catalysis of the Mizoroki-Heck Reaction and the Suzuki–Miyaura Coupling of Aryl Bromides

Abstract: A combination of Pd and Ni complexes activated aryl bromides for the thermal Mizoroki-Heck reaction and Suzuki coupling giving high yields in short reaction times. A thermal redox mechanism probably occurs whereby Ni complex transfers electron and reduces the Pd (II) to Pd (0) which then takes the reactants through the standard protocol of oxidative-addition, migratory insertion and reductive elimination, typical for the Mizoroki-Heck reaction and the Suzuki coupling. Graphic Abstract: [Figure not available: see fulltext.]