Tributyltin hydride

Tributyltin hydride

Tributyltin hydride, also known as TBT hydride, is an organotin compound with the chemical formula (C4H9)3SnH. It is a colorless liquid that is widely used in organic synthesis as a reducing agent and as a source of hydride ions. TBT hydride is highly reactive and has a wide range of applications in various industries.

Chemical Properties

Tributyltin hydride is a pyrophoric compound, meaning it can ignite spontaneously in air. It is soluble in organic solvents such as ether and benzene, but insoluble in water. TBT hydride reacts readily with water, alcohols, and acids, releasing hydrogen gas. It is important to handle this compound with caution due to its reactivity.

Synthesis

Tributyltin hydride can be synthesized through the reaction of tributyltin chloride with lithium aluminum hydride. The reaction proceeds as follows:

3 (C4H9)3SnCl + 4 LiAlH4 → 3 (C4H9)3SnH + 4 LiCl + 4 AlCl3

This reaction is typically carried out under an inert atmosphere, such as nitrogen or argon, to prevent the compound from reacting with moisture or oxygen in the air.

Applications

TBT hydride is primarily used as a reducing agent in organic synthesis. It can selectively reduce various functional groups, such as carbonyl compounds, nitro groups, and double bonds. The hydride ion (H-) provided by TBT hydride acts as a strong nucleophile, attacking electrophilic centers in organic molecules.

In addition to its role as a reducing agent, TBT hydride is also used as a source of hydride ions in various reactions. It can be employed in the reduction of metal salts, such as palladium and platinum, to form metal nanoparticles. These nanoparticles find applications in catalysis and materials science.

Safety Considerations

Tributyltin hydride is a highly reactive compound and should be handled with care. It is flammable and can ignite spontaneously in air. It reacts violently with water, alcohols, and acids, releasing flammable hydrogen gas. Proper safety precautions, such as working under an inert atmosphere and using appropriate protective equipment, should be followed when handling this compound.

See Also

• Organotin compound
• Reducing agent
• Hydride ion