602-55-1

Basic information

• Product Name: 9-PHENYLANTHRACENE
• Synonyms: anthracene,9-phenyl-;9-PHENYLANTHRACENE;Phenylanthracene,98%;9-PHENYLANTHRACENE OEKANAL, 250 MG;9-Phenylanthracene97%;9-Phenylanthracene 97%;9-Phenylanthracene,98%;NSC 90796
• CAS NO: 602-55-1
• Molecular Formula: C₂₀H₁₄
• Molecular Weight: 254.33
• EINECS: 210-019-8
• Product Categories: Aromatics Compounds;Anthracenes;Aromatics;Alpha Sort;Chemical Class;Hydrocarbons;NeatsVolatiles/ Semivolatiles;P;PAHsAlphabetic;PER - POLA;P-SAnalytical Standards;Arenes;Building Blocks;Organic Building Blocks;Building Blocks;Chemical Synthesis;Organic Building Blocks
• Mol File: 602-55-1.mol
• Article Data: 152

Chemical Properties

• Melting Point: 153-155 °C(lit.)
• Boiling Point: 417°C
• Flash Point: 192.1 °C
• Appearance: Off-white to pale brown/Solid
• Density: 1.1180 (estimate)
• Vapor Pressure: 8.86E-07mmHg at 25°C
• Refractive Index: 1.7040 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Sensitive: Light Sensitive
• BRN: 1910570
• CAS DataBase Reference: 9-PHENYLANTHRACENE(CAS DataBase Reference)
• NIST Chemistry Reference: 9-PHENYLANTHRACENE(602-55-1)
• EPA Substance Registry System: 9-PHENYLANTHRACENE(602-55-1)

Safety Data

• Hazard Codes: N
• Statements: 50/53
• Safety Statements: 60-61
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 3
• HazardClass: 9
• Hazardous Substances Data: 602-55-1(Hazardous Substances Data)

Usage

Chemical Properties

Pale Yellow Plates

Preparation

Phenylboronic acid (2.13 g, 17.49 mmol), 9- bromoanthracene (3 g, 11.66 mmol), Pd(PPh3)4 (140 mg, 0.12 mmol), K2CO3 (16 mL, 2 M), and ethanol (8 mL) were mixed in a 100 mL flask containing anhydrous toluene (32 mL). The mixture was refluxed for 48 h under nitrogen. After cooled to room temperature, the reaction mixture was quenched with dilute hydrochloric acid solution and extracted with CH2Cl2. The organic extracts were dried over anhydrous MgSO4 and concentrated by rotary evaporation. The crude product was further purified by silica gel column chromatography (CH2Cl2/petroleum ether (1:4,v/v)) to get a white powder (2.43 g, 81.9 %). 1H NMR (500 MHz, CDCl3) δ 8.53 (s, 1H), 8.08 (d, J = 8.5 Hz, 2H), 7.70 – 7.67 (m, 2H), 7.63 – 7.54 (m, 3H), 7.50 – 7.45 (m, 4H), 7.37 (ddd, J = 8.7, 6.5, 1.2 Hz, 2H). EI-MS (m/z): Calculated for C20H14: 254.33. Found [M+]: 253.02. Synthesis of 9-phenylanthracene

Synthesis Reference(s)

Journal of the American Chemical Society, 79, p. 393, 1957 DOI: 10.1021/ja01559a042

Purification Methods

Chromatograph it on alumina in *C6H6 and recrystallise it from AcOH or toluene. [Beilstein 5 H 725, 5 II 639, 5 III 2462.]

InChI:InChI=1/C20H14/c1-2-8-15(9-3-1)20-18-12-6-4-10-16(18)14-17-11-5-7-13-19(17)20/h1-14H

Upstream product

• 90-44-8 anthracen-9(10H)-one 
• 860728-94-5 10-methoxy-10-phenyl-anthrone-hydrazone 
• 141-52-6 sodium ethanolate 
• 111-24-0 1,5-dibromo-pentane 
• 40807-34-9 9-phenylanthracene cation radical 
• 1159-86-0 o-dibenzoylbenzene 
• 7664-93-9 sulfuric acid 
• 126530-66-3 9-phenyl-9-hydroxyantracen 
• 13577-28-1 9-phenyl-9,10-dihydroanthracene 
• 716-53-0 9-chloroanthracene 
• 98-80-6 phenylboronic acid 
• 1564-64-3 9-Bromoanthracene 
• 780-69-8 triethoxyphenylsilane 
• 110-71-4 1,2-dimethoxyethane 

Downstream Products

• 14325-34-9 9-ethoxy-9-phenyl-10-anthrone 
• 24451-63-6 (phenyl)(9-phenylanthracen-10-yl)methanone 
• 116706-33-3 C₂₅H₂₃P 
• 123676-14-2 12-(p-nitrobenzoyl)-1,3-dichloro-6-phenyl-11,12-dihydro-6,11<1',2'>-benzeno-6H-dibenz<1,4>oxazocine 
• 17803-81-5 10-phenyl-9-acetoxyanthracene 
• 120-12-7 anthracene 
• 203-33-8 benzo[a]fluoranthene 
• 76411-30-8 1,5-Diphenyl-3,4:7,8:9,10:11,12-tetrabenzotricyclo<4.2.2.2^2,5>dodeca-3,7,9,11-tetraen 
• 13225-66-6 1,2,3,4-Tetrahydro-9-phenylanthracene 
• 125379-29-5 1,2,3,4,5,6,7,8-Octahydro-9-phenylanthracene 
• 23674-20-6 9-bromo-10-phenylanthracene 
• 23102-67-2 10,10'-diphenyl-9,9'-bianthracene 
• 2022-42-6 9-fluoro-10-phenylanthracene 
• 76411-36-4 12-Phenyl-1,2,4a,4b,12b,12c-hexahydrobenzo<3,4>cyclobuta<1,2-a>anthracen 

Relevant articles and documents

CeO2/Pd Nanoparticles Incorporated Fly Ash Zeolite: An Efficient and Recyclable Catalyst for Csp2-Csp2 Bond Formation Reactions

The catalytic activity of CeO2 and palladium nanoparticles supported fly ash zeolite (CeO2/Pd@FAZ) for Csp2-Csp2 bond formation was studied. CeO2/Pd@FAZ was characterized by FTIR, XRD, EDAX and TEM studies. In the Suzuki-Miyauracross-coupling reaction, biphenyl derivatives with excellent yields were obtained, and the reaction conditions were optimized. The catalytic activity was explored using a wide variety of diversely substituted aryl bromides and chlorides with aryl boronic acid under optimized reaction conditions. The recyclability of the catalyst was established for three cycles, with the conversion rate from 99 to 40percent, which gained the advantage of heterogeneous catalysis.

Palladium and nickel catalysed Suzuki cross-coupling of sterically hindered aryl bromides with phenylboronic acid

Nickel and palladium catalysts for the Suzuki cross-coupling of aryl halides bearing two ortho substituents with phenylboronic acid have been developed and used for the synthesis of sterically hindered biaryls. (C) 2000 Elsevier Science Ltd.

A colorimetric chemodosimeter for Pd(II): a method for detecting residual palladium in cross-coupling reactions

A colorimetric chemodosimeter (SQ1) for the detection of trace palladium salts in cross-coupling reactions mediated by palladium is described. Decolorization of SQ1 is affected by nucleophilic attack of ethanethiol in basic DMSO solutions. Thiol addition is determined to have an equilibrium constant (Keq) of 2.9×106 M-1, with a large entropic and modest enthalpic driving force. This unusual result is attributed to solvent effects arising from a strong coordinative interaction between DMSO and the parent squaraine. Palladium detection is achieved through thiol scavenging from the SQ1-ethanethiol complex leading to a color 'turn-on' of the parent squaraine. It was found that untreated samples obtained directly from Suzuki couplings showed no response to the assay. However, treatment of the samples with aqueous nitric acid generates a uniform Pd(NO3)2 species, which gives an appropriate response. 'Naked-eye' detection of Pd(NO3)2 was estimated to be as low as 0.5 ppm in solution and instrument-based detection was tested as low as 100 ppb. The average error over the working range of the assay was determined to be 7%.

Agro-Waste Generated Pd/CAP-Ash Catalyzed Ligand-Free Approach for Suzuki–Miyaura Coupling Reaction

Abstract: We converted agro-waste Custard Apple Peels (CAP) to ash via thermal treatment, on which Pd(OAc)2 was immobilized easily that produced a low-cost, highly efficient Pd/CAP-ash catalyst. The prepared catalyst was fully characterized by using FT-IR, SEM, EDX, XRF, DSC-TGA, BET, HR-TEM, and XPS techniques. The Pd/CAP-ash catalyst was conveniently applied for the Suzuki–Miyaura coupling reaction under external base free and ligand-free conditions in an aqueous-organic solvent to produce biphenyls in good to excellent yields. The main attraction of our protocol an application of palladium-supported agro-waste material which is easily recoverable and recyclable provides mono and bis-coupled derivatives in a short reaction time. Graphic Abstract: [Figure not available: see fulltext.].

Novel compound and organic light emitting device comprising the same

The present invention provides a novel compound and an organic light emitting device using the same. The present invention provides a compound represented by chemical formula 1. The compound represented by chemical formula 1 described above can be used as a material for an organic layer of the organic light emitting device, and can improve efficiency, low driving voltage, and/or lifespan characteristics in the organic light emitting device.