Triisopropylsilyl acetylene

Physical Data colorless clear liquid bp 50-52 °C at 0.8 hPa (0.6 mmHg), flash point 56 °C (closed cup) d = 0.813. 

Solubility soluble in most organic solvents unknown water solubility. 

Handling, Storage, and Precautions stable to air and moisture incompatible with strong acids, bases, or oxidants flammable vapor and liquid skin/eye contact and inhalation should be avoided. 

Transition Metal-catalyzed Coupling Reactions. TIPS-acetylene has been widely used for transition metal-catalyzed coupling reactions with a variety of aryl-X and vinyl-X (X = 1, Br, Cl, and OTf) compounds as useful electrophiles in the presence of proper cocatalysts or additives, leading to the corresponding ethynyl-functionalized derivatives. 

Treatment of TIPS-acetylene with aryl (eq 1) and vinyl halides (eqs 2 and 3) and triflates (eq 4) and an appropriate Pd(0) catalyst (Sonogashira coupling) in the presence of copper(l) as cocatalyst affords arylalk3mes and enynes in good 3ueld. 

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In certain cases copper catalyzed processes might also be used for the N-alkynylation of azoles. Methyl indole-3-carboxylate was coupled with 1-bromo-2-triisopropylsilyl-acetylene in the presence of a copper-phenantroline catalyst to give the desired 1-ethynylindole derivative in excellent yield (6.74.),105... 

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