690-52-8

Basic information

• Product Name: tri-tert-butoxysilanethiol
• CAS NO: 690-52-8
• Molecular Weight: 280.504
• Mol File: 690-52-8.mol
• Article Data: 0

Chemical Properties

• CAS DataBase Reference: tri-tert-butoxysilanethiol(CAS DataBase Reference)
• NIST Chemistry Reference: tri-tert-butoxysilanethiol(690-52-8)
• EPA Substance Registry System: tri-tert-butoxysilanethiol(690-52-8)

Safety Data

• Hazardous Substances Data: 690-52-8(Hazardous Substances Data)

Usage

Description

Tri-tert-butoxysilanethiol, also known as (t-butoxy)3SiSH, is an organosilicon compound characterized by its three tert-butoxy groups attached to a central silicon atom, which is connected to a thiol (-SH) group. This unique structure endows it with specific chemical properties, making it a versatile reagent in various chemical reactions.

Uses

Used in Polarity Reversal Catalysis:
Tri-tert-butoxysilanethiol is used as an efficient hydrogen donor and catalyst in the context of polarity reversal catalysis in radical chain reactions. Its ability to donate hydrogen effectively facilitates the transformation of polar compounds, enhancing the efficiency and selectivity of the reactions.
Used in Chemical Synthesis:
In the chemical synthesis industry, tri-tert-butoxysilanethiol is used as a reagent for the synthesis of various organic and organosilicon compounds. Its unique structure allows it to participate in a wide range of reactions, including cross-coupling, reduction, and protection/deprotection processes, making it a valuable tool for chemists.
Used in Material Science:
Tri-tert-butoxysilanethiol is also utilized in the development of new materials, such as polymers and coatings, due to its ability to form stable siloxane bonds. Its use in material science contributes to the creation of innovative materials with improved properties, such as enhanced durability, thermal stability, and resistance to environmental factors.

Preparation

this reagent can be prepared by alcoholysis of silicon disulfide (SiS2).1,2 Representative procedure: powdered silicon disulfide (95% pure; 20.2 g, 0.21 mol) was charged into a 100 ml round-bottomed flask containing a robust stirrer bar and equipped with a reflux condenser. t-Butyl alcohol (60.0 g, 0.81 mol) was added and the mixture was stirred and heated under reflux under nitrogen for 72 h. The cooled reaction mixture was filtered through Celite to remove unreacted silicon disulfide and the filter cake was washed with diethyl ether. Excess of alcohol and diethyl ether were removed from the filtrate by rotary evaporation and the residual oil was distilled under reduced pressure to give the silanethiol (18.1 g, 31%) as a colorless liquid, bp 95 °C/15 mmHg, 113–115 °C/35 mmHg).

Downstream Products

• 1330777-07-5 [Ni(tri-tert-butoxysilanethiolato)2(3,5-dimethylpyridine)2(H₂O)]*benzene 
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