Tributylphosphine

Tributylphosphine is a chemical compound with the formula (C4H9)3P. It is a colorless liquid that is soluble in organic solvents. This compound is used as a ligand in organometallic chemistry and as a reagent in organic synthesis.

Structure and Bonding

Tributylphosphine is a phosphine with three butyl groups attached to a central phosphorus atom. The phosphorus atom is in the +3 oxidation state. The molecule is tetrahedral, similar to other phosphines and ammonia.

Synthesis

Tributylphosphine can be synthesized by the reaction of chlorobutane with phosphine in the presence of a base. The reaction proceeds via nucleophilic substitution.

Applications

Tributylphosphine is used as a ligand in organometallic chemistry. It forms complexes with many transition metals. These complexes are used in catalysis, including the hydroformylation of alkenes.

In organic synthesis, tributylphosphine is used as a reagent in the Wittig reaction, which is used for the synthesis of alkenes from aldehydes or ketones.

Safety

Tributylphosphine is a flammable liquid. It can cause burns and eye damage. It is harmful if swallowed, inhaled, or in contact with skin.

See also

• Phosphine
• Organophosphorus compound
• Wittig reaction