1564-64-3

white to light yellow crystal powder

9-Bromoanthracene(1564-64-3) acts as an intermediate in the preparation of 9-substituted derivative of the polycyclic aromatic hydrocarbon (PAH) anthracene.

The Sonogashira reaction of 9-Bromoanthracene(1564-64-3) and ethynyltrimethylsilane gave not only the expected anticipated 9-(trimethylsilylethynyl)anthracene and 2-(trimethylsilyl)aceanthrylene and (E)-4-(9-anthracenyl)-1,3-bis(trimethylsilyl)-but-3-en-1-yne were also obtained in moderate yields. The mechanistic principle may be that the coupling of bromo(anthracenyl)bis(triphenylphosphine)palladium(II) can occur either directly or after coordination and migratory insertion of the free alkyne.

The Journal of Organic Chemistry, 57, p. 2740, 1992 DOI: 10.1021/jo00035a038

General procedure for the synthesis of 9-bromoanthracene from anthracene: A mixture of anthracene (356 mg, 2 mmol), potassium bromide (143 mg, 1.2 mmol), acetic acid (9 mL), water (1 mL), and dichloromethane (5 mL) was added sequentially to a three-necked flask equipped with a condenser. A thermometer was inserted into the reaction system and the flask was transferred to a thermostatically heated magnetic stirring water bath. ZnAl-BrO3-LDHs (1.8 g, 1.8 mmol) was added slowly in batches over 15 min. The reaction temperature was controlled to be 40 °C. The reaction progress was monitored by thin layer chromatography (TLC). After 5 h of reaction, the reaction solution was washed with sodium sulfite solution and then extracted with dichloromethane (3 × 10 mL). The organic phases were combined and two scoops of column chromatography silica gel (200-300 mesh) were added to the dichloromethane phase and the organic solvent was removed by evaporation. Purification by column chromatography (eluent was petroleum ether: ethyl acetate = 15:1) under vacuum gave 468 mg of the target product 9-bromoanthracene as a pale yellow solid in 91% yield.

9-Bromoanthracene(1564-64-3) could be used to synthesise 6-bromoaceanthrylene-1,2-dione by Friedel-Crafts acylation reaction with oxalyl chloride. The pure 9-Bromoanthracene’s energy level is -5.710 eV. A 1:1 co-crystal of Picric acid and 9-Bromoanthracene was prepared by a solvent evaporation method. The PIC: BRA co-crystal shows significantly reduced impact sensitivity relative to pure Picric acid. The primary non-covalent interaction occurs between the electron-poor π-system of Picric acid and the electron-rich π-system of 9-Bromoanthracene. The distance between the Picric acid centroid and the 9-Bromoanthracene centroid was measured to be 3.492 ?, a typical value in materials which exhibit aromatic face-to-face πinteractions (<4.00 ?). An interaction is also indicated between aromatic hydrogen on the 9-Bromoanthracene ring and nitro group oxygen on a parallel Picric acid ring (C3-H3…O6). The donor-acceptor π ... π interactions dominate the formation of the Picric Acid co-crystal. The π electron cloud of the 9-Bromoanthracene ring is concentrated towards the electron-poor region at the centre of the Picric acid moiety, and the two rings combine. The π system of picric acid is known to deform due to the electron-withdrawing effect of nitro groups and an electron vacancy formed at the centre of the ring. This is partially filled by π electrons of the 9-Bromoanthracene ring. In other words, a charge transformation complex is formed[4].

Crystallise 9-bromoanthracene from MeOH or EtOH followed by sublimation in vacuo. [Masnori et al. J Am Chem Soc 108 126 1986, Beilstein 5 IV 2295.]