1055-26-1

Basic information

• Product Name: 1,2,3-Triphenylazulene
• Synonyms: 1,2,3-Triphenylazulene
• CAS NO: 1055-26-1
• Molecular Formula: C₂₈H₂₀
• Molecular Weight: 356.46
• Mol File: 1055-26-1.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 483.6°C at 760 mmHg
• Flash Point: 245°C
• Appearance: /
• Density: 1.116g/cm³
• Vapor Pressure: 4.86E-09mmHg at 25°C
• Refractive Index: 1.659
• CAS DataBase Reference: 1,2,3-Triphenylazulene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3-Triphenylazulene(1055-26-1)
• EPA Substance Registry System: 1,2,3-Triphenylazulene(1055-26-1)

Safety Data

• Hazardous Substances Data: 1055-26-1(Hazardous Substances Data)

Usage

General Description

1,2,3-Triphenylazulene is a polycyclic aromatic hydrocarbon compound with a unique azulene core structure. It is a deep blue, crystalline solid that is insoluble in water but soluble in organic solvents. 1,2,3-Triphenylazulene is often used as a dye and pigment in various applications such as colorimetric sensors, organic light emitting diodes (OLEDs), and photovoltaic devices. It exhibits strong fluorescence and has potential in optoelectronic applications due to its high thermal and chemical stability. Additionally, it has been studied for its potential use in organic electronics and as a building block for the synthesis of functional materials.

InChI:InChI=1/C28H20/c1-5-13-21(14-6-1)26-24-19-11-4-12-20-25(24)27(22-15-7-2-8-16-22)28(26)23-17-9-3-10-18-23/h1-20H

Upstream product

• 501-65-5 diphenyl acetylene 
• 73183-34-3 bis(pinacol)diborane 
• 16510-49-9 1,2,3-triphenylcyclopropene 
• 23147-72-0 1,2,3-triphenylcyclopropenyl bromide 
• 21473-32-5 trans-Δ¹-3β-(1'β,2'β,3'β-Triphenyl-cyclopropyl)-1,2,3-triphenyl-cyclopropen 
• 40814-98-0 cis-Δ¹-3β-(1'β,2'β,3'β-Triphenyl-cyclopropyl)-1,2,3-triphenyl-cyclopropen 
• 5271-67-0 2-Thiophenecarbonyl chloride 
• 528-76-7 2,4-dinitrobenzenesulfenyl chloride 

Relevant articles and documents

Palladium-Catalyzed [3 + 2] Annulation of Alkynes with Concomitant Aromatic Ring Expansion: A Concise Approach to (Pseudo)azulenes

The construction of (pseudo)azulenes represents an appealing yet challenging task in organic synthetic chemistry. Herein, we disclose a palladium-catalyzed [3 + 2] annulation technique of alkynes with concomitant aromatic ring expansion driven by a diboron reagent and iodide, affording a concise approach to azulenes (7-fused-5 bicycle) and pseudoazulenes (6-fused-5 bicycle). Compared with the documented synthetic strategies, the route to (pseudo)azulenes developed herein is applicable for both homo- and cross-annulation processes and exhibits a broad substrate scope. It is worth noting that this transformation is not only suitable for the ring expansion of the phenyl moiety to afford azulenes but also applicable to the ring expansion of the electron-rich five-membered heterocycles to deliver pseudoazulenes. Experimental and computational investigations on the mechanism support the formal trans-palladium-boration across the alkyne, cis-addition of the alkyne, dearomative spiroannulation, and aromatic ring expansion process.

The reaction of (η5-cyclopentadienyl)dicarbonyliron(2-thienoyl) with acetylenes; a mechanistic study using proton nuclear magnetic resonance, and application in synthesis

The thermal reaction of dicarbonyl-η5-cyclopentadienyl(2-thienoyl)iron with a series of substituted acetylenes to give indenones and cyclopentathiophenones have been reinvestigated.The results obtained support a reaction mechanism involving initial acetylene insertion followed by that of carbon monoxide, in contradiction to the previously reported results.The reaction products were identified and characterized primarily using 2D 1H nmr spectroscopy.

GENERATION OF AZULENE RADICAL CATION FROM ARYLALKYNES

If a diarylalkyne 4-XC6H4CCR (R=Ph, 4-MeC6H4, or 4-ButC6H4) or 1-phenylpropyne in trifluoroacatic acid containing mercury(II) trifluoroacetate is irradiated with u.v. light filtered through Pyrex glass, the e.s.r. spectrum of the corresponding azulene can be obsreved.The azulenes have been isolated and converted back into their radical cations by irradiation in trifluoroacetic acid, or in dichloromethane containing (4-BrC6H4)3N+. or (2,4-Br2C6H3)3N+..Possible mechanisms by which the azulenes are formed the alkynes are discussed.