Uses
2,7-Dibromo-9,10-dihydro-9,9-dimethylacridine is an intermediate in the synthesis of 2,7-Diisopropyl-9,9-dimethyl-4a,9,9a,10-tetrahydroacridine (D455760). 2,7-Diisopropyl-9,9-dimethyl-4a,9,9a,10-tetrahydroacridine is a useful chemical reagent. Also, it is derived from 9,9-Dimethyl-9,10-dihydroacridine (D474300), which are currently being used in the development of thermally activated delayed fluorescence (TADF) molecules which are being researched for their possible efficient deep-?blue TADF emitting potential.
Synthesis
9,9-Dimethyl-9,10-dihydroacridine (2.7 g, 12.93 mmol) was dissolved in chloroform (200 ml) under the protection of nitrogen (by N2 purge) with continuous stirring. Subsequently, 3 equivalents of bromine were added slowly and dropwise. After 8 hours of reaction, the reaction was quenched by addition of aqueous sodium thiosulfate. The reaction mixture was then subjected to an extraction process. Purification by column chromatography using a solvent mixture of methylene chloride (MC) and hexane (1:5) as the unfolding agent resulted in 2,7-dibromo-9,9-dimethyl-9,10-dihydroacridine as a white solid (4.24 g, 90% yield).
References
[1] Patent: US2018/166636, 2018, A1. Location in patent: Paragraph 0115; 0116
[2] Patent: WO2014/165307, 2014, A2. Location in patent: Paragraph 0321
