4-((Trimethylsilyl)ethynyl)phenol Chemical Properties

Melting point:

68 °C

Boiling point:

251.7±32.0 °C(Predicted)

Density 

1.01±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

solid

pka

9.26±0.26(Predicted)

color 

White to light yellow

Safety Information

HS Code 

2931900090

4-((Trimethylsilyl)ethynyl)phenol Usage And Synthesis

Synthesis

The general procedure for the synthesis of (4-hydroxyphenylacetylene)trimethylsilane from 4-iodophenol and trimethylsilylacetylene was as follows: 4-iodophenol (2 g, 9.09 mmol, 1 equiv) was dissolved in 20 mL of anhydrous toluene. To this solution was sequentially added PdCl2(PPh3)2 (191.4 mg, 0.27 mmol, 0.03 eq.), copper(I) iodide (172.8 mg, 0.909 mmol, 0.1 eq.), N,N-diisopropylethylamine (1.58 mL, 9.09 mmol, 1 eq.), followed by trimethylsilylacetylene (1.28 mL. 9.09 mmol, 1 equiv). The reaction mixture was stirred at room temperature for 24 hours. Upon completion of the reaction, the solvent was removed by evaporation and the residue was purified by column chromatography (eluent: EtOAc/hexane = 1:10) to afford the target product (4-hydroxyphenylacetylene)trimethylsilane (1.73 g, quantitative yield) as a brown oil. The structure of the product was confirmed by 1H-NMR (CDCl3, 500 MHz) and 13C-NMR (CDCl3, 75 MHz): 1H-NMR δ 7.37 (2H, d, J = 8.8 Hz, Ar-H), 6.76 (2H, d, J = 8.8 Hz, Ar-H), 4.92 (1H, brs, Ar-OH), 0.24 (9H , s, -Si(CH3)3); 13C-NMR δ 155.76, 133.69, 115.49, 115.31, 105.02, 92.50, 0.05.

References

[1] Chemical Communications, 2009, # 39, p. 5832 - 5834
[2] Angewandte Chemie - International Edition, 2012, vol. 51, # 37, p. 9311 - 9316
[3] Angew. Chem., 2012, vol. 124, # 37, p. 9445 - 9450,6
[4] Bulletin of the Korean Chemical Society, 2013, vol. 34, # 4, p. 1247 - 1249
[5] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2015, vol. 70, # 9, p. 637 - 641