Phenyl formate is an organic compound with the formula , often abbreviated as HCOOPh, where Ph stands for phenyl. It is a colorless liquid with a characteristic sweet, fruity odor. It is the phenyl ester of formic acid.
Phenyl formate is synthesized by the esterification reaction between formic acid and phenol at 105 ðC for 4 hours, in toluene as a solvent, using an acid as a catalyst such as p-toluenesulfonic acid.
Phenyl formate releases carbon monoxide and phenol under relatively mild conditions, often catalyzed by a weak base, like tertiary amines.
This property of phenyl formate avoids the necessity of direct usage of carbon monoxide and the hazards of high toxicity and flammability associated with it.
The chemical control of the rate of carbon monoxide generation is the key to the development of the external carbon monoxide-free palladium-catalyzed phenoxycarbonylation of haloarenes at room temperature. Because of the mild reaction conditions and wide range of substrates, the phenoxycarbonylation makes a general, safe, and practical method to synthesize arenecarboxylic acid esters.
Phenyl formate is used as a flavoring agent in the food industry. It is also used for the formylation of amines.
The reaction of phenyl formate with ammonia, primary and secondary amines (known as aminolysis) results in the formation of formamides and phenol.