1608-40-8

Basic information

• Product Name: 1,4-bis[(Z)-2-phenylethenyl]benzene
• Synonyms: 1,4-bis[(Z)-2-phenylethenyl]benzene;(Z,Z)-p-Distyrylbenzene;1,4-Bis[(Z)-styryl]benzene
• CAS NO: 1608-40-8
• Molecular Formula: C₂₂H₁₈
• Molecular Weight: 282.38
• Mol File: 1608-40-8.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 443.6°C at 760 mmHg
• Flash Point: 217.7°C
• Appearance: /
• Density: 1.103g/cm³
• Vapor Pressure: 1.19E-07mmHg at 25°C
• Refractive Index: 1.719
• CAS DataBase Reference: 1,4-bis[(Z)-2-phenylethenyl]benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-bis[(Z)-2-phenylethenyl]benzene(1608-40-8)
• EPA Substance Registry System: 1,4-bis[(Z)-2-phenylethenyl]benzene(1608-40-8)

Safety Data

• Hazardous Substances Data: 1608-40-8(Hazardous Substances Data)

Usage

Type of Compound

Aromatic hydrocarbon

Structure

Three phenyl rings connected by carbon-carbon double bonds

Usage in Organic Synthesis

Building block for various materials

Applications

a. Polymers
b. Liquid crystals
c. Electronic and optoelectronic devices (OLEDs, organic photovoltaic cells)

Pharmaceutical Applications

a. Fluorescent probe for detecting DNA
b. Component in the development of new drugs

InChI:InChI=1/C22H18/c1-3-7-19(8-4-1)11-13-21-15-17-22(18-16-21)14-12-20-9-5-2-6-10-20/h1-18H/b13-11-,14-12+

Upstream product

• 100-42-5 styrene 
• 106-37-6 1.4-dibromobenzene 
• 1849-27-0 1,4-bis(2-phenylethynyl)benzene 
• 20767-31-1 benzyl(triphenyl)phosphonium bromide 
• 623-27-8 terephthalaldehyde, 

Downstream Products

• 191-24-2 Benzo[ghi]perylene 
• 167999-32-8 ((C5H5)Co)2(β,α,1,2-η:β',α',4,3-η-(p-distyrylbenzene)) 
• 27759-00-8 C₄₄H₃₂ 

Relevant articles and documents

Chemoselective semihydrogenation of alkynes catalyzed by manganese(i)-PNP pincer complexes

A general manganese catalyzed chemoselective semihydrogenation of alkynes to olefins in the presence of molecular hydrogen is described. The best results are obtained by applying the aliphatic Mn PNP pincer complex Mn-3c which allows the transformation of various substituted internal alkynes to the respective Z-olefins under mild conditions and in high yields. Mechanistic investigations based on experiments and computations indicate the formation of the Z-isomer via an outer-sphere mechanism.

Copper-catalysed, diboron-mediated: Cis -dideuterated semihydrogenation of alkynes with heavy water

Methods to incorporate deuterium atoms into organic molecules are valuable for the pharmaceutical industry. Here, we found that diboron reagents can efficiently mediate the transfer of two D atoms from heavy water directly onto alkynes through copper-catalysed cis-selective semihydrogenation. Avoiding the use of costly and flammable D2 gas, this safe and practical process can proceed with excellent chemoselectivity and stereoselectivity. Utilizing the present method as the key step, the formal asymmetric total synthesis of d2-deuterium-labeled cis-combretastatin A4 is demonstrated. Mechanistic studies suggest that monoborylation of alkynes is the key step for this semihydrogenation process.