3-Phenyl-2-propyn-1-ol

clear colorless to yellow liquid

An phenylacetylene derivative with inhibitory effect on nitrification in soil. It has potential bactericidal and fungicidal activity.

3-Phenyl-2-propyn-1-ol is an phenyl acetylene derivative with inhibitory effect on nitrification in soil.

Journal of Medicinal Chemistry, 40, p. 1230, 1997 DOI: 10.1021/jm960467d
Synthetic Communications, 26, p. 3593, 1996 DOI: 10.1080/00397919608003770

Iodobenzene 8.0 g (39.2 mmol) was dissolved in tetrahydrofuran 50 mL and triethylamine 7.93 g (78.4 mmol), bis(triphenylphosphine)palladium(II) dichloride 566 mg (0.784 mmol) and copper(I) iodide 519 mg (2.74 mmol) were added to it under an ice bath and stirred for 30 minutes. To this was added propargyl alcohol dropwise with a dropping funnel 2.20 g (39.2 mmol) of tetrahydrofuran solution in 10 mL was warmed to room temperature, stirred for 30 min, and the reaction was terminated by passing through a short column (silica gel 64-210 m diam., 1.5 cm I.D. x 25 cm H). The product was washed three times with saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated to give a brown oily substance 6.29 g. The substance was treated by silica gel column chromatography (289 g, 2.1 cm i.d. x 40 cm long) with hexane-ethyl acetate (0-20-100%, step-gradient method) as the eluent to give 3-phenyl-2-propyn-1-ol (brown oily substance. 4.56 g) (88% yield).