1714-09-6

Basic information

• Product Name: 1-Phenylanthracene
• Synonyms: 1-Phenylanthracene
• CAS NO: 1714-09-6
• Molecular Formula: C₂₀H₁₄
• Molecular Weight: 254.33
• Mol File: 1714-09-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-Phenylanthracene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Phenylanthracene(1714-09-6)
• EPA Substance Registry System: 1-Phenylanthracene(1714-09-6)

Safety Data

• Hazardous Substances Data: 1714-09-6(Hazardous Substances Data)

Usage

Appearance

Bright yellow solid

Solubility

Insoluble in water and most organic solvents, soluble in hot aromatic solvents

Usage

Production of organic light-emitting diodes (OLEDs), component in the synthesis of dyes and pigments

Properties

Fluorescence, photochemical behavior

Applications

Organic electronics, optoelectronics, chemical reaction mechanisms, and photophysics studies

Precautions

Potential environmental contaminant, may pose health risks

Upstream product

• 1714-14-3 1-phenyl-anthraquinone 
• 120-12-7 anthracene 
• 58109-40-3 diphenyliodonium hexafluorophosphate 
• 57835-99-1 triphenylsulphonium hexafluorophosphate 
• 14381-66-9 1,8-dichloroanthracene 
• 1903-13-5 4-phenylanthrone 
• 7397-92-4 1-bromoanthracene 
• 1515-78-2 buta-1,3-dien-1-ylbenzene 
• 3485-80-1 1-iodo-9,10-anthraquinone 
• 859334-21-7 1-phenyl-1,4-dihydro-anthraquinone 
• 591-51-5 phenyllithium 
• 34420-17-2 (2-phenylethyl)boronic acid 
• 1638147-40-6 C₁₆H₁₄O₄ 
• 22980-71-8 8,10-dichloroanthracene 

Relevant articles and documents

Tris-NHC-propagated self-supported polymer-based Pd catalysts for heterogeneous C-H functionalization

Three-dimensionally propagated imidazolium-containing mesoporous coordination polymer and organic polymer-based platforms were successfully exploited to develop single-site heterogenized Pd-NHC catalysts for oxidative arene/heteroarene C-H functionalization reactions. The catalysts were efficient in directed arene halogenation, and nondirected arene and heteroarene arylation reactions. High catalytic activity, excellent heterogeneity and recyclability were offered by these systems making them promising candidates in the area of heterogeneous C-H functionalization, where efficient catalysts are still scarce.

Probing mechanisms of aryl-aryl bond cleavages under flash vacuum pyrolysis conditions

Several biaryls have been subjected to flash vacuum pyrolysis (FVP) at 1100°C and 0.8-0.9hPa. Product compositions are reported for the FVP of 9-phenylanthracene (1), 2-bromobiphenyl (5), biphenyl (8), 1,10- diphenylanthracene (12), 9-(2-naphthyl)anthracene (17), and 9,9′- bianthracenyl (20). The experimental results have been used to evaluate four possible mechanistic pathways for the cleavage of aryl-aryl bonds under these conditions: (1) the 'explosion' of substituted phenyl radicals; (2) hydrogen atom attachment to an ipso-carbon atom of the biaryl followed by C-C bond cleavage; (3) direct homolysis; and (4) loss of a fragment as an aryne. None of these mechanisms by itself successfully accommodates all of the experimental facts. The data suggest that aryl-aryl bond cleavages under FVP conditions involve at least two different mechanistic pathways and that the relative contributions of the competing pathways probably vary from one biaryl to the next.

Palladium-catalyzed allenylation/intramolecular diels-alder reaction of furans with propargyl carboxylates for the synthesis of polycyclic compounds

A highly efficient palladium-catalyzed cascade reaction of propargyl carboxylates bearing a furanyl group with organoborons was developed. This methodology offers rapid access to polycyclic Diels-Alder cycloadducts in good to high yields. The thus-formed oxygen-bridged products were further converted into anthracene derivatives in a chemoselective manner under mild conditions. Copyright

5,6,7,12-Tetrahydrodibenz[c,f][1,5]azabismocines: Highly reactive and recoverable organo-bismuth reagents for cross-coupling reactions with Aryl Bromides

Hypervalent organobismuth compounds efficiently couple with aryl bromides in the presence of [Pd(PPh3)4] catalyst. Application of this protocol to a one-pot multi-coupling reaction with bromophenylboronic esters leads to the formation of up to nine bonds in good yields (see scheme).

Electron trasfer sensitized photolysis of 'onium salts

We have studied the anthracene-sensitized photolyses of both diphenyliodonium and triphenylsulphonium salts in solution using both steady-state and laser flash photolysis techniques.Photoproducts, namely, phenylated anthracenes along with iodobenzene or diphenylsulfide, respectively, are obtained from both salts with quantum efficiencies of ca. 0.1 at 375 nm.We infer the intermediacy of diphenyliodo and triphenylsulphur radicals formed by single electron transfer from the singlet-excited anthracene.We have developed a quantitative model of this chemistry, and identify the principal sources of inefficiency as back electron transfer, which occurs at nearly the theoretically limiting rate, intersystem crossing from the initially formed sensitizer-'onium salt encounter complex, and in-cage radical recombination.

Reactions of the 1,8-Diphenylanthracene System

An improved synthesis of 1,8-diphenylanthracene (1) is described along with various reactions of this hydrocarbon, including electrophilic substitution reactions, oxidations, and addition of n-BuLi.The molecular geometry of a derivative, 10-bromo-1,8-diphenylanthracene (20), was determined by X-ray crystallography.Of the various routes explored for forming 9-substituted 1,8-diphenylanthracenes, only the addition of certain organometallic reagents to the 9-anthrone 10 was satisfactory.