3-Phenyl-1-propyne

3-PHENYL-1-PROPYNE can be prepared by reacting trimethylethynylsilane with benzyl bromide in the presence of isopropyl magnesium chloride and copper bromide.

Step A: Trimethylethynylsilane (23g, 233.88mmol) and 100ml THF were added to i-PrMgCl (2min THF 117ml, 233.88mmol) at 0℃ and stirred for 30min. The mixture was then heated to room temperature and stirred for 30min. CuBr (5.03g, 35.08mmol) and benzyl bromide (10g, 58.47mmol) were added and the mixture was refluxed for 5h. The mixture was cooled to room temperature, ethyl acetate was added, and the mixture was washed with water. Column chromatography was then performed to obtain 9.2g of liquid, yield: 83.5%.

Step B: The compound from Step A (9.2 g, 48.85 mmol) and 100 ml of methanol were cooled in an ice bath. Potassium carbonate (33.76 g, 244.2 mmol) was added and stirred for 2 h. The mixture was stirred overnight at room temperature. Ethyl acetate was added, and the mixture was washed with water. After concentration, 5 g of an oily substance, 3-PHENYL-1-PROPYNE, was obtained.

Clear colorless to yellow liquid

3-Phenyl-1-propyne is used as a starting material in the synthesis of 4-phenyl-2-butyn-1-ol. It is also used in the preparation of beta-hydroxytriazoles and indoles.

The Journal of Organic Chemistry, 47, p. 1837, 1982 DOI: 10.1021/jo00349a007

3-Phenyl-1-propyne is a 3-aryl-1-propyne. The electronic transition of the resonance-stabilized 1-phenylpropargyl radical, produced in a jet-cooled discharge of 3-phenyl-1-propyne, has been studied by laser-induced fluorescence excitation and dispersed single vibronic level fluorescence (SVLF) spectroscopy. The microwave rotational spectrum of 3-phenyl-1-propyne (propargyl benzene) has been studied and its stable conformation is reported to have coplanar carbon atoms. Reaction of N-methyl-N-phenylhydrazine or N-phenylhydrazine with 3-phenyl-1-propyne is reported to yield indoles. 3-Phenyl-1-propyne is reported to react with styrene oxide and sodium azide, to afford β-hydroxytriazoles.