Uses
4-Ethynylbenzonitrile is used as a synthetic fragment and as a test compound for cross-coupling reactions. It is used in the study of hydrogen bond formation in multifunctional molecules due to the presence of four hydrogen bonding sites. It is also involved in the preparation of 4-[(trimethylsilyl)ethynyl]benzonitrile.
Synthesis
General procedure for the synthesis of 4-ethynylbenzonitrile from 4-[(trimethylsilyl)ethynyl]benzyl cyanide: potassium carbonate (50 mg, 0.36 mmol) was added to a mixed methanol/tetrahydrofuran solution (16 mL, 1:1) of 4-[(trimethylsilyl)ethynyl]benzyl cyanide (1.1 g, 5.3 mmol). The reaction mixture was stirred at room temperature for 30 min, followed by removal of the solvent by rotary evaporator. The residue was diluted with ethyl acetate and washed sequentially with 10% aqueous hydrochloric acid and saturated saline. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 4-ethynylbenzonitrile as a white solid (0.61 g, 4.80 mmol, 91% yield).
References
[1] Tetrahedron, 2003, vol. 59, # 3, p. 287 - 293
[2] Journal of Medicinal Chemistry, 1998, vol. 41, # 21, p. 4036 - 4052
[3] Journal of the American Chemical Society, 1997, vol. 119, # 43, p. 10401 - 10412
[4] Journal of Organic Chemistry, 2014, vol. 79, # 16, p. 7342 - 7357
[5] New Journal of Chemistry, 2017, vol. 41, # 6, p. 2296 - 2308
