Tributylphosphine

Tributylphosphine is the organophosphorus compound with the formula P(C4H9)3. Abbreviated or PBu3, it is a tertiary phosphine. It is an oily liquid at room temperature, with a nauseating odor. It reacts slowly with atmospheric oxygen, and rapidly with other oxidizing agents, to give the corresponding phosphine oxide. It is usually handled using air-free techniques. Tributylphosphine is the organophosphorus compound with the formula P(C4H9)3. Abbreviated or PBu3, it is a tertiary phosphine. It is an oily liquid at room temperature, with a nauseating odor. It reacts slowly with atmospheric oxygen, and rapidly with other oxidizing agents, to give the corresponding phosphine oxide. It is usually handled using air-free techniques. Tributylphosphine is prepared industrially by the addition of phosphine to butene: the addition proceeds by a free radical mechanism, and so the Markovnikov rule is not followed. Tributylphosphine can be prepared in the laboratory by reaction of the appropriate Grignard reagent with phosphorus trichloride although, as it is commercially available at reasonable prices, it is rare to have to perform the small-scale preparation.