42196-97-4

Basic information

• Product Name: (E)9-(2-phenylvinyl)anthracene
• Synonyms: (E)9-(2-phenylvinyl)anthracene;TRANS-STYRYLANTHRACENE;STYRYLANTHRACENE;9-[(E)-Styryl]anthracene;Einecs 255-705-8
• CAS NO: 42196-97-4
• Molecular Formula: C₂₂H₁₆
• Molecular Weight: 280.36244
• EINECS: 255-705-8
• Mol File: 42196-97-4.mol
• Article Data: 16

Chemical Properties

• Melting Point: 132 °C
• Boiling Point: 476.4°Cat760mmHg
• Flash Point: 236.5°C
• Appearance: /
• Density: 1.163g/cm³
• Vapor Pressure: 8.8E-09mmHg at 25°C
• Refractive Index: 1.762
• CAS DataBase Reference: (E)9-(2-phenylvinyl)anthracene(CAS DataBase Reference)
• NIST Chemistry Reference: (E)9-(2-phenylvinyl)anthracene(42196-97-4)
• EPA Substance Registry System: (E)9-(2-phenylvinyl)anthracene(42196-97-4)

Safety Data

• Hazardous Substances Data: 42196-97-4(Hazardous Substances Data)

Usage

General Description

(E)9-(2-phenylvinyl)anthracene is a polycyclic aromatic hydrocarbon compound with a molecular formula of C24H18. It is a derivative of anthracene, consisting of a nine-carbon anthracene core with a vinyl group substituted at the 9 position and a phenyl group at the 2 position. (E)9-(2-phenylvinyl)anthracene is commonly used in organic synthesis and has been studied for its potential applications in materials science and optoelectronics. (E)9-(2-phenylvinyl)anthracene exhibits fluorescent properties and has been investigated for its use in organic light-emitting diodes (OLEDs) and other electronic devices. It is important to handle (E)9-(2-phenylvinyl)anthracene with caution, as it is classified as a hazardous chemical with potential health and environmental risks.

InChI:InChI=1/C22H16/c1-2-8-17(9-3-1)14-15-22-20-12-6-4-10-18(20)16-19-11-5-7-13-21(19)22/h1-16H

Upstream product

• 100-42-5 styrene 
• 1564-64-3 9-Bromoanthracene 
• 103-82-2 phenylacetic acid 
• 108-86-1 bromobenzene 
• 2444-68-0 9-vinylanthracene 
• 100-39-0 benzyl bromide 
• 61592-89-0 2,2’-dibromodiphenylmethane 
• 103-26-4 Methyl cinnamate 
• 583-53-9 2,3-dibromobenzene 
• 123335-02-4 bis-(2-bromophenyl)methanol 
• 87337-07-3 1-(9'-anthracenyl)-2-phenylethyne 
• 2417-77-8 9-bromoethylanthracene 
• 642-31-9 9-anthracene aldehyde 
• 6921-34-2 benzylmagnesium chloride 

Downstream Products

• 87337-07-3 1-(9'-anthracenyl)-2-phenylethyne 
• 87337-00-6 cis-1-(9-anthryl)-2-phenylethylene 
• 97635-19-3 C₄₄H₃₂ 
• 97635-21-7 C₄₄H₃₂ 
• 97635-20-6 C₄₄H₃₂ 
• 123676-16-4 12-(p-nitrobenzoyl)-1,3-dichloro-6-trans-styryl-11,12-dihydro-6,11<1',2'>-benzeno-6H-dibenz<1,4>oxazocine 

Relevant articles and documents

9-vinylanthracene based fluorogens: Synthesis, structure-property relationships and applications

Fluorescent dyes with aggregation-induced emission (AIE) properties exhibit intensified emission upon aggregation. They are promising candidates to study biomolecules and cellular changes in aqueous environments when aggregation formation occurs. Here, we report a group of 9-position functionalized anthracene derivatives that were conveniently synthesized by the palladium-catalyzed Heck reaction. Using fluorometric analyses, these dyes were confirmed to show AIE behavior upon forming aggregates at high concentrations, in viscous solvents, and when poorly solubilized. Their photophysical properties were then further correlated with their structural features, using density functional theory (DFT) calculation. Finally, we demonstrated their potential applications in monitoring pH changes, quantifying globular proteins, as well as cell imaging with confocal microscopy.

N-Heterocyclic carbene palladium (II)-pyridine (NHC-Pd (II)-Py) complex catalyzed heck reactions

A mild, efficient, and practical catalytic system for the synthesis of highly privileged stilbene pharmacophores is reported. This system uses N-heterocyclic carbene palladium (II) Pyridine (NHC-Pd (II)-Py) complex to catalyze the formation of carbon-carbon bonds between olefin derivatives and various bromide. This simple, gentle and user-friendly method can offer a variety of stilbene products in excellent yields under solvent-free condition. And its scale-up reaction has excellent yield and this system can be applied to industrial fields. The utility of this method is highlighted by its universality and modular synthesis of a series of bioactive molecules or important medical intermediates.

Synthesis and tyrosinase inhibition activity of trans-stilbene derivatives

Synthesis of a focussed library of trans-stilbene compounds through Wittig and other base catalysed condensation reactions is presented. The synthesized stilbenes were screened for their inhibitory potential against murine tyrosinase activity to explore the structure activity relationship (SAR). Presence of electron withdrawing group (-CN) at the double bond and hydroxyl group or halogen atom especially at para-position on the aromatic rings was found to significantly elevate the inhibitory activity. Among all the compounds screened, compounds 2, 6, 8, 10, 11, 15 and 21 were found to exhibit appreciable inhibitory activity. Compound 21 ((E)-2,3-bis(4-Hydroxyphenyl)acryonitrile) was found to be the most active with an IC50 value of 5.06 μM which is less than half of the value 10.78 μM observed for resveratrol (common standard used in murine tyrosinase activity studies) under similar conditions. The results obtained from the present study reveal structural/functional group sensitivity for the tyrosinase inhibitory activity of stilbenoid moieties and are expected to be very helpful for the design and synthesis of novel, selective and effective tyrosinase inhibitors.