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Tributylphosphine: Applications in Organic Synthesis and its Health Hazards

Oct 23，2024

Description

Tributylphosphine(TBP) 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-faree techniques.

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Reactions

Tributylphosphine (TBP) is a powerful reductant that need to be present in only slight molar excess for the complete reduction of disulfides; moreover, it do not react with thiol-specific reagents and do not give rise to gas formation during the reaction.

Applications in Organic Synthesis

Tributylphosphine finds some industrial use as a catalyst modifier in the cobalt-catalyzed hydroformylation of alkenes, where it greatly increases the ratio of straight-chain aldehydes to branched-chain aldehydes in the product mixture.

It is the precursor to the pesticide (2,4-dichlorobenzyl)tributylphosphonium chloride ("Phosfleur").¹

Tributylphosphine is a common ligand for the preparation of complexes of transition metals in low oxidation states. It is cheaper and less air-sensitive than trimethylphosphine and other trialkylphosphines.

Health Hazards

Tributylphosphine is moderately toxic, with an LD50 of 750 mg/kg (oral, rats).

Reference

1.Jürgen Svara, Norbert Weferling and Thomas Hofmann "Phosphorus Compounds, Organic" in Ullmann's Encyclopedia of Industrial Chemistry, 2006, Wiley-VCH, Weinheim. doi:10.1002/14356007.a19_545.pub2

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