TRIISOPROPYLSILANETHIOL Property

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.

pka

9.86±0.10(Predicted)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

RIDADR 

UN 3334

WGK Germany 

3

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

TRIISOPROPYLSILANETHIOL Chemical Properties,Usage,Production

Physical properties

bp 70–73 °C (2 mmHg); d 0.887 g cm?3.

Uses

Triisopropylsilanethiol 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.