2-Bromo-5-fluorobenzonitrile (CAS number 57381-39-2) is a benzonitrile derivative, bearing a bromide and a fluoride at the 2- and 5-positions. The bromide and fluoride substituents display different reactivities, thus enabling selective substitution reactions. Fluoride favors nucleophilic aromatic substitution, while bromide is amenable to Pd-catalyzed coupling reactions. A thermally activated delayed fluorescence (TADF) dye, named as 2-phenoxazine-5-acridine-benzonitrile, is synthesized from 2-bromo-5-fluorobenzonitrile with phenoxazines, carbazoles or acridan in a two-step reaction that includes nucleophilic aromatic substitution and Buchwald-Hartwig amination. The resulting OLED device shows a maximum current efficiency of 16.3 cdA-1, a maximum powder efficiency of 12.2 lmW-1 and an external quantum efficiency of 5%.
The ortho positioning of bromide and nitrile groups of 2-bromo-5-fluorobenzonitrile facilitates its synthesis into quinazolines for the use in antitumour and anti-inflammatory applications.