Triisopropylhydrosilane

Product Introduction

Triisopropylhydrosilane (CAS No. 6485-79-6) is a sterically hindered organosilicon hydride containing one Si–H bond and three isopropyl substituents.

The Si–H bond gives Triisopropylhydrosilane useful reducing and hydrogen-transfer properties, while the bulky isopropyl groups provide steric hindrance that can influence reaction selectivity.

Triisopropylhydrosilane is used in organic synthesis, reduction chemistry, deoxygenation, reductive transformations, protecting-group chemistry, hydrosilylation, and organosilicon synthesis. TCI also lists applications involving Triisopropylsilylation of alcohols and identifies the compound under reducing and protecting agents.

Mechanism / Principle

Hydrosilane Reactivity

The central reactive feature of Triisopropylhydrosilane is its Si–H bond.

Under appropriate reaction conditions, the Si–H bond can participate in hydrogen-transfer or hydrosilylation processes, allowing the reagent to be used in transformations such as:

• Reduction of organic functional groups
• Reductive deoxygenation
• Hydrosilylation
• Radical-mediated transformations
• Reductive deprotection

The steric bulk around silicon can help differentiate Triisopropylhydrosilane from less hindered hydrosilanes.

Triisopropylsilyl Chemistry

Triisopropylhydrosilane is also associated with TIPS chemistry. The bulky triisopropylsilyl group is widely used as a protecting group for hydroxyl functionalities.

TCI specifically lists protection of hydroxyl groups, including 1,2- and 1,3-diols, among the related applications of CAS 6485-79-6.

Key Research Applications

1. Organic Reduction

Triisopropylhydrosilane can serve as a hydrosilane reducing reagent in organic synthesis.

Applications include:

• Selective reduction
• Reductive transformations
• Functional-group conversion
• Synthetic intermediate preparation
• Methodology development

2. Deoxygenation

The Si–H bond makes Triisopropylhydrosilane useful in selected deoxygenation reactions.

Applications include:

• Reductive deoxygenation
• Alcohol-derived substrate transformations
• Oxygen-functional-group removal
• Complex molecule synthesis

3. Hydroxyl Protection

Triisopropylhydrosilane is associated with TIPS-based protecting-group chemistry for hydroxyl-containing compounds.

Applications include:

• Alcohol protection
• Diol protection
• Polyol chemistry
• Carbohydrate synthesis
• Natural-product synthesis

TCI cites literature on TIPS protection of hydroxyl groups and specifically references applications involving 1,2- and 1,3-diols.

4. Peptide and Pharmaceutical Synthesis

Triisopropylhydrosilane can be used in selected reductive transformations involved in complex organic synthesis.

Applications include:

• Peptide-related synthesis
• Pharmaceutical intermediates
• Protecting-group chemistry
• Multistep organic synthesis
• Medicinal chemistry

5. Hydrosilylation

The Si–H functionality can participate in catalytic hydrosilylation reactions with suitable unsaturated substrates.

Applications include:

• Alkene hydrosilylation
• Alkyne hydrosilylation
• Organosilicon synthesis
• Catalytic silicon chemistry

6. Radical Chemistry

Triisopropylhydrosilane can function as a hydrogen donor in selected radical-mediated synthetic transformations.

Applications include:

• Radical reduction
• Radical deoxygenation
• Hydrogen-transfer reactions
• Synthetic methodology development

Advantages

• Contains a reactive Si–H bond
• Sterically hindered hydrosilane structure
• Useful reducing reagent
• Suitable for selected deoxygenation reactions
• Applicable to hydrosilylation chemistry
• Useful in TIPS protecting-group chemistry
• Suitable for complex organic synthesis
• Applicable to pharmaceutical and natural-product research
• Useful in organosilicon chemistry
• Available in high-purity research grades

Storage & Handling

• Store in a tightly closed container.
• Protect from moisture and atmospheric humidity.
• Store in a cool, dry and well-ventilated environment.
• TCI recommends storage at room temperature in a cool and dark place, preferably below 15°C, under inert gas. 
• Minimize exposure to air and moisture.
• Keep away from heat, sparks, and ignition sources.
• Handle in a suitable fume hood.
• Avoid contact with skin and eyes.
• Wear appropriate gloves, protective clothing, and eye protection.
• Follow the product-specific SDS for handling, storage, transportation, and disposal.

TCI identifies Triisopropylsilane as moisture sensitive and recommends storage under inert gas.

Research Areas

Researchers working in the following fields may benefit from Triisopropylhydrosilane (CAS No. 6485-79-6):

• Organic chemistry
• Synthetic chemistry
• Organosilicon chemistry
• Medicinal chemistry
• Pharmaceutical chemistry
• Peptide chemistry
• Natural-product synthesis
• Radical chemistry
• Reduction chemistry
• Protecting-group chemistry
• Hydrosilylation
• Materials and silicon chemistry

Q1: What is Triisopropylhydrosilane?

A: Triisopropylhydrosilane is an organosilicon hydride with CAS No. 6485-79-6, molecular formula C₉H₂₂Si, and molecular weight 158.36 g/mol.

Q2: Is Triisopropylhydrosilane the same as Triisopropylsilane?

A: Yes. Triisopropylhydrosilane and Triisopropylsilane refer to the same compound, CAS 6485-79-6. Major chemical suppliers use Triisopropylsilane as the primary product name for this CAS.

Q3: What is the abbreviation for Triisopropylhydrosilane?

A: TIPS or TIS may be used as abbreviations. In synthetic chemistry, TIPS is also commonly associated with the bulky triisopropylsilyl group.

Q4: What is Triisopropylhydrosilane used for?

A: It is used as a hydrosilane reagent in organic reduction, deoxygenation, hydrosilylation, protecting-group chemistry, and synthetic methodology development.

Q5: What is the molecular weight of Triisopropylhydrosilane?

A: The molecular weight is 158.36 g/mol. NIST reports 158.3565 g/mol.

Q6: What is the molecular formula of CAS 6485-79-6?

A: The molecular formula is C₉H₂₂Si.

Q7: Is Triisopropylhydrosilane moisture sensitive?

A: Yes. Commercial specifications identify CAS 6485-79-6 as moisture sensitive and recommend storage under inert gas.

Q8: Can Triisopropylhydrosilane be used in hydroxyl protection chemistry?

A: Yes. CAS 6485-79-6 is associated with TIPS-based hydroxyl protection chemistry, including protection strategies for 1,2- and 1,3-diols.