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

• 67-66-3 chloroform 
• 519-73-3 triphenylmethane 
• 90-44-8 anthracen-9(10H)-one 
• 5471-63-6 1,3-diphenylisobenzofuran 
• 16587-39-6 1,3-diphenylbenzo[c]thiophene 
• 71-43-2 benzene 
• 111-24-0 1,5-dibromo-pentane 
• 108-88-3 toluene 
• 642-31-9 9-anthracene aldehyde 
• 280-57-9 1,4-diaza-bicyclo[2.2.2]octane 
• 7664-93-9 sulfuric acid 
• 7111-67-3 1,3-diphenyl-1,3-dihydroisobenzofuran 
• 7449-50-5 1,1-diphenyl-1,3-dihydrobenzofuran 
• 1159-86-0 o-dibenzoylbenzene 

Downstream Products

• 1251-77-0 9-(4-nitro-phenyl)-10-phenyl-anthracene 
• 13577-28-1 9-phenyl-9,10-dihydroanthracene 
• 5146-30-5 10-phenyl-10-hydroxy-9-anthracenone 
• 17803-81-5 10-phenyl-9-acetoxyanthracene 
• 23674-20-6 9-bromo-10-phenylanthracene 
• 134450-66-1 9-phenyl-10-nitroanthracene 
• 54440-48-1 9-phenyl-9,10-dihydro-9,10-epidioxido-anthracene 
• 55255-70-4 9-cyclohexyl-tetradecahydro-anthracene 
• 24451-63-6 (phenyl)(9-phenylanthracen-10-yl)methanone 
• 24451-69-2 9-(chloromethyl)-10-phenylanthracene 
• 24451-66-9 9-bromomethyl-10-phenyl-anthracene 
• 92844-38-7 cis-9,10-diethyl-10-phenyl-9,10-dihydroanthracene 
• 98-82-8 Isopropylbenzene 
• 99458-45-4 9-Nitro-9-phenyl-10-trinitromethyl-9,10-dihydro-anthracene 

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%.

Sterically enhanced 2-iminopyridylpalladium chlorides as recyclable ppm-palladium catalyst for Suzuki–Miyaura coupling in aqueous solution

Sterically hindered 2-iminopyridine derivatives and their palladium chlorides complexes are designed and prepared, which efficiently promote the Suzuki–Miyaura coupling (SMC) reaction in aqueous solution. Besides the good to excellent yields and broad substrate scope, these catalysts can be reused for at least four new batches of the substrates. Spontaneous separation of coupling products in the aqueous reaction medium is the additional striking feature of this catalytic process. Furthermore, catalytic performance of palladium complexes bearing the azo-bridged phenyl groups was greatly influenced by the UV irradiation due to the cis/trans photoisomerization of azo unit of the catalysts. In conclusion, titled palladium complexes provide a green, sustainable, cost-effective, and convenient process to synthesize SMC products at multi-gram-scale reaction.

Synthesis of tetranuclear complex of Pd(II) with thiosemicarbazone ligands derived from 2-quinolone and its catalytic evaluation in Suzuki–Miyaura-type coupling reactions and alkoxylation of chloroquinolines

A tetranuclear palladium(II) complex [(Pd(H-6MOQtsc-Ph))4] was obtained from the reaction between 6-methyl-2-oxo-1,2-dihydroquinoline-3-carboxaldehyde-4(N)-phenylthiosemicarbazone [H2-6MOQtsc-Ph] and K2[PdCl4]. The ligand and the Pd(II) complex were characterized by Fourier transform infrared spectroscopy (FT-IR), UV–visible and 1H NMR spectroscopy. X-ray diffraction studies confirmed the tetrameric nature of the complex with the coordination of ligand through quinolone carbonyl, azomethine nitrogen and thiolate sulfur atoms, and the fourth site is occupied by 2-quinolone nitrogen atom of the adjacent ligand. The synthesized complex was tested as catalyst in Suzuki–Miyaura coupling reaction between various chloroquinoline derivatives with phenylboronic acid. The reactions afforded unexpected C-alkoxylated (C-O coupling) products instead of more expected C-arylated (C-C coupling) products in the respective alcoholic mediums. However, the reactions with traditional aryl halides probed with very good yield of the corresponding C-C coupling products.