9-phenylanthracene

Chemical properties

Pale Yellow Plates

The Uses of 9-phenylanthracene

9-Phenylanthracene is used to synthesize organic light-emitting material intermediates.

Preparation

The synthesis of 9-phenylanthracene involved mixing 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) in a 100 mL flask with 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.]