2-(TRIMETHYLSILYLETHYNYL)PYRIDINE Chemical Properties

Melting point:

42 °C

Boiling point:

85 °C

Density 

0.95±0.1 g/cm3(Predicted)

refractive index 

1.5330

Flash point:

85-86°C/1mm

storage temp. 

Inert atmosphere,2-8°C

pka

4.29±0.19(Predicted)

form 

clear liquid

color 

Colorless to Light orange to Yellow

Water Solubility 

Insoluble in water.

BRN 

4176916

CAS DataBase Reference

86521-05-3

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

HS Code 

29333990

2-(TRIMETHYLSILYLETHYNYL)PYRIDINE Usage And Synthesis

Chemical Properties

Clear colorless to yellow liquid

Uses

2-(Trimethylsilylethynyl)pyridine is used as a pharmaceutical intermediate.

Synthesis

General procedure for the synthesis of 2-pyridinylalkynyltrimethylsilanes from 2-bromopyridine and trimethylsilylethynes: 100 mL of diisopropylamine solution containing 2-bromopyridine (4.74 g, 0.030 mol), CuI (0.14 g, 0.74 mmol), and Pd(PPh3)2Cl2 (0.52 g, 0.74 mmol) was added to a solution containing 2-bromopyridine (4.74 g, 0.030 mol), CuI (0.14 g, 0.74 mmol), and Pd(PPh3)2Cl2 (0.52 g, 0.74 mmol), protected by nitrogen. trimethylsilylacetylene (3.0 g, 0.030 mol). The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure and the residue was purified to give 5.0 g (95% yield) of 2-(trimethylsilyl)ethynylpyridine.

References

[1] Synthesis, 1983, # 4, p. 312 - 314
[2] Canadian Journal of Chemistry, 2005, vol. 83, # 6-7, p. 716 - 727
[3] Phosphorus, Sulfur and Silicon and Related Elements, 2002, vol. 177, # 5, p. 1041 - 1045
[4] Patent: WO2006/93466, 2006, A1. Location in patent: Page/Page column 28
[5] Journal of Organometallic Chemistry, 2009, vol. 694, # 9-10, p. 1317 - 1324

2-(TRIMETHYLSILYLETHYNYL)PYRIDINE(86521-05-3)Related Product Information

• 3-(TRIMETHYLSILYLETHYNYL)PYRIDINE
• 4-(Trimethlysilyl-ethynyl)pyridine
• 2-[2-(TRIMETHYLSILYL)ETHYNYL]-4-PICOLINE
• 2-[2-(TRIMETHYLSILYL)ETHYNYL]-6-PICOLINE
• 2-[2-(TRIMETHYLSILYL)ETHYNYL]-5-PICOLINE
• 2,6-BIS(TRIMETHYLSILYLETHYNYL)PYRIDINE
• 4,6-DIMETHYL-2-TRIMETHYLSILANYLETHYNYL-NICOTINONITRILE
• 5-BROMO-2-[2-(TRIMETHYLSILYL)ETHYNYL]PYRIDINE
• 2-(TRIMETHYLSILYLETHYNYL)PYRIDINE
• 2-TRIMETHYLSILANYLETHYNYL-3-CYANOPYRIDINE
• 5-FLUORO-2-[2-(TRIMETHYLSILYL)ETHYNYL]PYRIDINE