Chemical Properties
White to off-white powder
Uses
2,4,6-
Tri-tert-butylnitrobenzene (bulky amine) was used in the synthesis of monomeric iminophosphorane.
Uses
2,4,6-Tri-tert-butylnitrobenzene (bulky amine) is used in the synthesis of monomeric iminophosphorane
Definition
ChEBI: 2,4,6-tri-tert-butylaniline is an alkylbenzene.
Synthesis
The general procedure for the synthesis of 2,4,6-tri-tert-butylaniline from 2,4,6-tri-tert-butylnitrobenzene was as follows: in a 4 mL glass reaction flask equipped with a septum cap and a magnetic stirring bar, Co-Co3O4Chit-700 catalyst (10 mg, 3.4 mol/kg Co), nitroaromatic hydrocarbons (0.5 mmol, 1.0 equiv), triethylamine ( 35 μL, 0.25 mmol, 0.5 equiv), and EtOH/H2O (3:1, 2 mL) mixed solvent. The reaction vial was placed in a 300 mL autoclave and pressurized to 40 bar after five displacements with hydrogen. The reaction mixture was stirred at 110 °C until the reaction was complete. At the end of the reaction, it was cooled to room temperature and the pressure in the autoclave was slowly released. The crude reaction mixture was filtered through a cotton fitted pipette and the filtrate was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: ethyl acetate), and pure 2,4,6-tri-tert-butylaniline derivatives were obtained after removing the solvent under reduced pressure. Using the catalyst of the present invention, efficient preparation of the target aniline derivatives from the corresponding nitroaromatics can be realized.
References
[1] ChemSusChem, 2017, vol. 10, # 15, p. 3035 - 3039
[2] Patent: WO2018/114777, 2018, A1. Location in patent: Page/Page column 31-32
[3] Journal of the American Chemical Society, 1991, vol. 113, # 22, p. 8437 - 8443
[4] Journal of the American Chemical Society, 1982, vol. 104, # 25, p. 7191 - 7195
[5] Chemistry - A European Journal, 2017, vol. 23, # 59, p. 14738 - 14742
