Triisopropylsilane

Product Introduction

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

Its Si–H bond enables Triisopropylsilane to act as a useful mild reducing agent and hydrosilane reagent in organic synthesis. The bulky isopropyl groups provide significant steric hindrance, which can influence its chemoselectivity and make it useful in selective reduction and deoxygenation reactions.

Triisopropylsilane is widely used in organic synthesis, peptide chemistry, reduction reactions, deprotection, deoxygenation, and hydrosilylation research. Commercial suppliers offer Triisopropylsilane in research grades such as 98% and >98% GC.

Mechanism / Principle

Hydrosilane Reduction

The reactive Si–H bond can transfer hydride equivalents to suitable substrates in the presence of appropriate reaction conditions or catalysts.

Triisopropylsilane can therefore participate in:

• Reduction of functional groups
• Deoxygenation reactions
• Reductive deprotection
• Radical-mediated reductions
• Catalytic hydrosilylation

The silicon-containing products formed during these reactions provide a thermodynamic driving force for many hydrosilane-mediated transformations.

Steric Effects

The three isopropyl groups surrounding silicon create a sterically demanding environment. This can help control the reactivity of the Si–H bond and can provide useful selectivity in synthetic applications.

Key Research Applications

1. Organic Reduction

Triisopropylsilane is used as a reducing reagent for a variety of organic substrates.

Applications include:

• Selective reduction
• Functional-group reduction
• Reductive transformations
• Organic synthesis
• Synthetic intermediate preparation

2. Deoxygenation Reactions

TIPS can be used in deoxygenation chemistry, particularly when selective removal of oxygen functionality is required.

Applications include:

• Deoxygenation of alcohol derivatives
• Reductive deoxygenation
• Oxygen-functional-group removal
• Synthetic route development

3. Peptide and Organic Synthesis

Triisopropylsilane is used as a reagent in synthetic chemistry involving complex organic molecules and peptide-related transformations.

Applications include:

• Peptide synthesis
• Protecting-group chemistry
• Reductive deprotection
• Pharmaceutical intermediate synthesis
• Natural-product synthesis

Commercial chemical databases also report its use as a peptide synthesis protecting-group reagent.

4. Reductive Deprotection

Triisopropylsilane can be used in reductive cleavage or deprotection strategies for selected protecting groups.

Applications include:

• Protecting-group removal
• Reductive cleavage
• Synthetic intermediate purification
• Multistep organic synthesis

5. Hydrosilylation

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

Applications include:

• Alkene hydrosilylation
• Alkyne hydrosilylation
• Catalytic organosilicon chemistry
• Silicon-containing molecule synthesis

6. Radical Chemistry

Triisopropylsilane can serve as a hydrogen donor in selected radical-mediated transformations.

Applications include:

• Radical reductions
• Radical deoxygenation
• Chain reactions
• Synthetic methodology development

Advantages

• Contains a reactive Si–H bond
• Useful hydrosilane reagent
• Can function as a mild reducing agent
• Sterically hindered silicon center
• Useful for selective organic transformations
• Applicable to deoxygenation reactions
• Suitable for reductive deprotection
• Useful in peptide and pharmaceutical synthesis
• Applicable to hydrosilylation 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, dark place, preferably below 15°C, under inert gas. 
• Avoid exposure to moisture.
• Keep away from heat, sparks, and open flames.
• 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.

Triisopropylsilane is classified as a flammable liquid. TCI reports a flash point of approximately 37°C, while other supplier data report similar flammability characteristics.

Research Areas

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

• Organic chemistry
• Synthetic chemistry
• Organosilicon chemistry
• Medicinal chemistry
• Pharmaceutical chemistry
• Peptide chemistry
• Natural-product synthesis
• Radical chemistry
• Catalytic reduction
• Chemical methodology development

Q1: What is Triisopropylsilane?

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

Q2: What is the abbreviation for Triisopropylsilane?

A: Triisopropylsilane is commonly abbreviated as TIPS or TIS.

Q3: What is Triisopropylsilane used for?

A: It is primarily used as a hydrosilane reducing reagent in organic synthesis, including reduction, deoxygenation, reductive deprotection, radical chemistry, and hydrosilylation.

Q4: Is Triisopropylsilane a reducing agent?

A: Yes. Its reactive Si–H bond allows Triisopropylsilane to function as a hydrogen/hydride source in suitable reduction reactions.

Q5: Is Triisopropylsilane moisture sensitive?

A: Yes. Commercial specifications identify Triisopropylsilane as moisture sensitive, so exposure to atmospheric moisture should be minimized.

Q6: What is the molecular weight of Triisopropylsilane?

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

Q7: What is the molecular formula of CAS 6485-79-6?

A: The molecular formula is C₉H₂₂Si.

Q8: Is Triisopropylsilane the same as Triisopropylhydrosilane?

A: Yes. Triisopropylsilane and Triisopropylhydrosilane refer to the same compound, CAS 6485-79-6.