Phenylacetyl

Phenylacetyl refers to the phenylacetyl group, a two-carbon acyl substituent with the structure Ph-CH2-CO-. It is derived from phenylacetic acid (Ph-CH2-COOH) and is encountered as part of larger molecules as either a substituent or as an acylating moiety. The group can be introduced by forming the corresponding acid chloride, phenylacetyl chloride (Ph-CH2-CO-Cl), which is a common reactive intermediate.

In organic synthesis, phenylacetyl groups are used to introduce the phenylacetyl moiety into molecules via acylation reactions. Phenylacetyl chloride readily reacts with nucleophiles such as amines and alcohols to form amide and ester derivatives, respectively. The chemistry of the group is influenced by the electron-rich phenyl ring and by the methylene linker, which can alter the carbonyl's reactivity compared with simpler acyl groups.

Phenylacetyl is also encountered as a substituent in various natural products and synthetic compounds where a phenylacetyl fragment contributes to lipophilicity and steric profile. Related compounds include phenylacetic acid and derivatives, as well as the acid chloride phenylacetyl chloride.

Safety and handling: Phenylacetyl chloride is a corrosive, lachrymatory reagent and should be handled with appropriate protective equipment and in a fume hood. Standard organic solvents and inert atmospheres are used as needed.

See also: phenylacetic acid, phenylacetyl chloride, acyl group, acylation.