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TRIISOPROPYLSILANETHIOL

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TRIISOPROPYLSILANETHIOL Basic information
TRIISOPROPYLSILANETHIOL Chemical Properties
  • Boiling point:70-75 °C2 mm Hg(lit.)
  • Density 0.887 g/mL at 25 °C(lit.)
  • refractive index n20/D 1.479(lit.)
  • Flash point:171 °F
  • solubility Soluble in most organic solvents.
  • pka9.86±0.10(Predicted)
Safety Information
  • Hazard Codes Xi
  • Risk Statements 36/37/38
  • Safety Statements 26-36
  • RIDADR UN 3334
  • WGK Germany 3
MSDS
TRIISOPROPYLSILANETHIOL Usage And Synthesis
  • Physical propertiesbp 70–73 °C (2 mmHg); d 0.887 g cm?3.
  • UsesTriisopropylsilanethiol is convenient synthetic equivalent of H2S for the synthesis of alkanethiols and unsymmetrical dialkyl sulfides; used as polarityreversal catalyst in radical reactions.
    1. Use as a Nucleophile: A Synthetic Equivalent of H2S. HSTIPS is prepared in quantitative yield (98%) from the reaction of LiSH (readily obtained by reacting H2S with n-BuLi in THF) with TIPSCl at ?78°C.
    2.Synthesis of 9-BBN-derived Alkyl and Aryl Boranes.
    3.Palladium-catalyzed Cross-coupling Reactions. The Pd0- catalyzed cross-coupling of vinyl and aryl halides with KSTIPS affords the corresponding silyl sulfides, which can be used either to prepare thiols or sulfides.
    4.Use as Ligand in Ziegler-Natta Polymerization of Ethylene in Solution. A medium pressure process for the polymerization of ethylene has been developed in the presence of a catalytic system involving a monocyclopentadienyl titanium species, containing TIPSthiolate as the heteroligand and two activable ligands (2Cl or 2Me), associated with an ionic activator such as triphenylcarbenium tetrakis(pentafluorophenyl)borate.
    5.Use in Radical Reactions. The radical reduction of alkyl halides by silanes is promoted by thiols. According to Roberts, the thiol acts as a polarity-reversal catalyst.6.
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