Triisopropylsilane

Triisopropylsilane

Triisopropylsilane, also known as TIPS, is a chemical compound with the molecular formula C9H22Si. It is an organosilicon compound that belongs to the class of alkylsilanes. TIPS is widely used in various chemical reactions and serves as a versatile reagent in organic synthesis.

Properties

Triisopropylsilane is a colorless liquid with a characteristic odor. It has a molecular weight of 162.36 g/mol and a boiling point of approximately 160°C. The compound is insoluble in water but soluble in organic solvents such as ethanol, ether, and chloroform.

Synthesis

Triisopropylsilane can be synthesized through the reaction of chlorotriisopropylsilane with lithium aluminum hydride. This reaction results in the reduction of the chlorosilane to the desired triisopropylsilane. Another method involves the reaction of trichlorosilane with isopropylmagnesium chloride, followed by purification.

Applications

Triisopropylsilane finds extensive use in organic synthesis as a reducing agent and protecting group. It is commonly employed in the reduction of various functional groups, including carbonyl compounds, nitro groups, and imines. TIPS is particularly useful in the reduction of esters to alcohols and ketones to secondary alcohols.

Additionally, triisopropylsilane is utilized as a protecting group for aldehydes and ketones. By converting these functional groups into their corresponding acetals or ketals using TIPS, chemists can selectively manipulate other parts of the molecule without affecting the protected carbonyl group. This strategy is often employed in complex organic synthesis to control regioselectivity and stereoselectivity.

Safety

Triisopropylsilane is considered to be a relatively safe compound when handled properly. However, it is important to take necessary precautions, such as wearing appropriate protective equipment (gloves, goggles, and lab coat) and working in a well-ventilated area. The compound should be stored in a cool, dry place away from sources of ignition.

See also

• Organosilicon compound
• Reducing agent
• Protecting group