Uses
1-propyl-1H-imidazole (PrIm) could be selected as a ligand for a study on homoleptic Fe(II)-Imidazole complexes, allowing for a comparison between the two systems. Its extreme versatility as a ligand was unveiled as it gave rise to a new family of Fe(II) complexes with mono-, bi- and tetranuclear members[1].
Synthesis
Synthesis of 1-propyl-1H-imidazole: Sodium hydride (55%, 0.966 g, 22.1 mmol) was slowly added to a solution of tetrahydrofuran (50.0 mL) of imidazole (1.37 g, 20.1 mmol) at room temperature. The reaction mixture was stirred at room temperature for 1 hour. Subsequently, 1-bromopropane (5.48 mL, 60.3 mmol) was added dropwise at the same temperature and the reaction solution was continued to be stirred for 16 hours. Upon completion of the reaction, the reaction mixture was filtered through a diatomaceous earth pad and the filter cake was washed with tetrahydrofuran. The filtrate and washings were combined and concentrated under reduced pressure to remove the solvent. The resulting crude product was purified by fast column chromatography (silica gel as stationary phase and chloroform/methanol as eluent) to afford 1-propyl-1H-imidazole (2.07 g, 18.8 mmol, 93% yield) as a colorless oil.1H NMR (400 MHz, CDCl3) δ: 0.93 (3H, t, J = 7.2 Hz), 1.81 (2H, td, J = 7.2, 14.4 Hz), 3.90 (2H, t, J = 7.2 Hz), 6.91 (1H, s), 7.06 (1H, s), 7.46 (1H, s).
References
[1] Willi Zeni. “A New Family of Fe(II) 1-Propyl-1H-Imidazole Complexes with Mono-, Bi-, and Tetra-Nuclear Members.” European Journal of Inorganic Chemistry 27 29 (2024).
