Triphenylphosphine oxide

Triphenylphosphine oxide

White to pale yellow solid with an unpleasant odor

Fixed

1.2 g · cm -3

155-158 ° C

> 360 ° C

Poorly in water

Attention

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Is triphenylphosphine, an organic phosphorus compound. It consists of a phosphorus atom to which the three phenyl radicals and an oxide bonded oxygen.

Production

Triphenylphosphine oxide often formed as a byproduct in reactions in which triphenylphosphine or its derivatives are used. For example, in Appel reaction, the Staudinger reaction, Mitsunobu reaction and the Wittig reaction.

It can be produced by oxidation of triphenylphosphine with oxygen, which is why triphenylphosphine after standing still contains a portion of triphenylphosphine oxide.

Properties

Triphenylphosphine oxide is a colorless solid melting at 155-158 ° C. It is poorly soluble in water, cyclohexane, carbon tetrachloride and acetonitrile. However, it is highly soluble in dichloromethane, chloroform, and short-chain alcohols such as methanol, ethanol and 1 -propanol.

The central phosphorus atom is tetrahedrally coordinated. In the lowest energy conformation of the phenyl are twisted against each other.

Triphenylphosphine oxide is a good ligand for hard metal centers.

Use

In organic chemistry, triphenylphosphine oxide is mainly used for the preparation of phosphorus ylides.