Synthesis
Potassium acetate (1.71 g, 17.4 mmol) was added to a solution of 4-bromoaniline (1.0 g, 5.8 mmol) and bis(pinacol)diboron (1.78 g, 7.0 mmol) in dioxane (15.0 mL). The reaction mixture was degassed with nitrogen for 30.0 min, and PdCl2(dppf) (0.21 g, 0.3 mmol) was added. The reaction was stirred at 100 °C for 6 h. The reaction progress was monitored by TLC. After the reaction was complete, dioxane was removed from the reaction mixture by evaporation, the residue was quenched with water, and the compound was extracted with ethyl acetate.
The organic layer was concentrated under reduced pressure to obtain a crude compound, which was then purified by Combi-flash™ column chromatography (4.0 g column) eluting with 20% ethyl acetate in hexane to give 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (0.65 g, 50.78%) as a pale yellow solid. MS: 220.20 [M+1].
Description
4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline is an important organic reagent with an appearance ranging from white to yellow to orange powder to crystal. This compound can be used as a chemical reaction reagent or for preparing fluorescent probes.
Uses
4-Aminophenylboronic acid pinacol ester can be used as a reagent for:
- The preparation of substituted 3-phenyl-4H-1-benzopyran-4-ones by reacting with iodochromones via Pd catalyzed Suzuki-Miyaura cross-coupling reaction.
- Mercury(II) detection by fluorometry with new fluorogenic indicators based on through-bond energy transfer from pentaquinone to rhodamine.
- Rhodium-catalyzed amination reactions.
- Palladium-catalyzed Suzuki cross-coupling to synthesize potential antitubercular and antimicrobial compounds.
It can also be used to prepare:
- Hexaphenylbenzene derivatives as a potential bioprobe and multichannel keypad system.
- Pyromellitic diimide-based polymer as matrix for solution-processable n-channel field-effect transistors.
- Alternating copolymers of oligoarylenes and naphthalene bisimides as low band-gap semiconductors with electrochemical and spectroelectrochemical behavior.
- γ-secretase modulators in the treatment of amyloid β formation.
