19227-07-7

Basic information

• Product Name: Azulene,2-phenyl-
• Synonyms: Azulene,2-phenyl-;2-Phenylazulene
• CAS NO: 19227-07-7
• Molecular Formula: C₁₆H₁₂
• Molecular Weight: 0
• Mol File: 19227-07-7.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 364.7°C at 760 mmHg
• Flash Point: 165°C
• Appearance: /
• Density: 1.081g/cm³
• Vapor Pressure: 3.48E-05mmHg at 25°C
• Refractive Index: 1.647
• CAS DataBase Reference: Azulene,2-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Azulene,2-phenyl-(19227-07-7)
• EPA Substance Registry System: Azulene,2-phenyl-(19227-07-7)

Safety Data

• Hazardous Substances Data: 19227-07-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C16H12/c1-3-7-13(8-4-1)16-11-14-9-5-2-6-10-15(14)12-16/h1-12H

Upstream product

• 623-73-4 diazoacetic acid ethyl ester 
• 26461-03-0 1-phenylindane 
• 22253-11-8 2-phenyl-2,3-dihydro-1H-indene 
• 106-38-7 para-bromotoluene 
• 457644-50-7 2-(azulen-2-yl)-4,4,5,5- tetramethyl-1,3,2-dioxaborolane 
• 106-37-6 1.4-dibromobenzene 
• 1069984-11-7 2-phenyl-1-azulenyl p-tolyl sulfone 
• 108-86-1 bromobenzene 
• 36044-41-4 2-iodoazulene 
• 591-50-4 iodobenzene 
• 1201-25-8 azulene-1-carboxylic acid 
• 98-86-2 acetophenone 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 4481-35-0 cyclohepta[b]furan-2(2H)-one 

Relevant articles and documents

Stereochemistry, Stereodynamics, and Redox and Complexation Behaviors of 2,2′-Diaryl-1,1′-Biazulenes

2,2′-Diaryl-1,1′-biazulenes were synthesized and electronic communication between the azulene subunits was suggested based on redox measurements. The linkage of azulene at the 1-position also appeared to increase the HOMO levels. In addition, cyclic voltammetry measurements of 2-arylazulenes showed a return peak associated with the oxidation, which was not observed for azulene. The stabilization of the single-electron oxidant may be due to the SOMO-HOMO energy inversion phenomenon. X-ray crystallography of the azulene dimers revealed that this species possessed a syn-type structure in which both aryl groups in the 2-positions formed π-stacks. The twisted structure was indicated to be in the (R)- or (S)-configuration for all molecules in the unit cell. Spontaneous resolution was also shown. Furthermore, from the solid circular dichroism (CD) spectral measurements, the relationship between the absolute configuration of the molecules and the CD spectra was determined. A racemization rotational barrier of ca. 27 kcal mol?1 was calculated. Moreover, the pyridylazulene dimer cyclized upon reaction with PdCl2 to form a 3 : 3 complex, in which the biazulene units cyclized to give ratios between the (R)- and (S)-forms of either 2 : 1 or 1 : 2.

Iridium-catalyzed dehydrogenative silylation of azulenes based on regioselective C-H bond activation

Use of an iridium catalyst allowed the efficient dehydrogenative functionalization of C-H bonds of azulenes with the production of hydrogen as the sole byproduct. The reaction occurred with excellent chemo- and regioselectivities to provide 2-silylazulene

Carboxylic Acid Directed C-H Arylation of Azulene

The first example of directed C-H activation for azulene is reported. A variety of 2-arylazulenes are obtainable exclusively from 1-azulene carboxylic acids, with yields of up to 82percent. Some heteroaryl groups such as pyridine and thiophene are also tolerated in the reaction. The efficacy of the reaction is found to be highly dependent on the conditions, with a phosphate base and a bulky carboxylic acid being key additives.