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Triphenylphosphine


Other Names:

Triphenylphosphane

Phosphorustriphenyl






General Information:


Structure:



CAS Number: 603-35-0

Molecular Weight: 262.29 g/mol

Appearance: White solid


Triphenylphosphine is often used as a reducing agent, leading to the formation of triphenylphosphine oxide. The reaction is driven by the formation of the thermodynamically favored P=O bond of triphenylphosphine oxide. Triphenylphosphine oxide is a side-product that can be difficult to separate from desired product. Triphenylphosphine oxide is often removed through chromatography. When exposed to air, triphenylphosphine slowly oxidizes to triphenylphosphine oxide.




Common Uses:


Reagent in Mitsunobu reactions





Reagent in Appel reactions





Reagent in Staudinger reactions





Reagent for phosphonium salt preparation (usually used later in Wittig reactions)





Safety:


For acute exposure triphenylphosphine is considered an irritant, for chronic exposure it poses neurological risks. Triphenylphosphine is incompatible with strong oxidizing agents.




References:


1) WO2015177325, page 70

2) WO2014152144, page 56

3) WO2015089337, page 185

4) WO2015177325, page 77

5) Burke, S. D.; Danheiser, R. L.; Handbook of Reagents for Organic Synthesis, Oxidizing and Reducing Agents

6) Wikipedia: Triphenylphosphine (link)

7) www.sigmaaldrich.com: Triphenylphosphine (link)