4Benzylaminobenzene

4-Benzylaminobenzene, also known as para‑benzylaniline or p‑(benzylamino)benzene, is an organic compound with the molecular formula C14H13N. Its IUPAC name is 4‑(benzylamino)benzenemethane, reflecting a benzene ring bearing a benzylamine substituent at the para position. The compound is a white crystalline solid with a melting point around 89–91 °C and is sparingly soluble in water but readily soluble in organic solvents such as ethanol, chloroform, and diethyl ether.

The synthesis of 4‑benzylaminobenzene typically proceeds from p‑chlorobenzylamine or p‑bromobenzylamine via nucleophilic aromatic substitution or metal‑catalyzed cross‑coupling reactions. A common route involves the condensation of p‑aminoacetophenone with benzyl chloride in the presence of a base, followed by reduction of the intermediate ketone. Alternative methods use the Buchwald‑Hartwig amination of p‑halobenzyl bromides with aniline derivatives.

This compound is useful as an intermediate in the synthesis of pharmaceuticals, dyes, and agrochemicals. Its benzylamine functionality is a good protecting group for amino groups during multistep syntheses. In medicinal chemistry, 4‑benzylaminobenzene derivatives have been explored as potential analgesic and anti‑inflammatory agents due to their ability to modulate the cyclooxygenase pathway. Additionally, the molecule serves as a building block for the preparation of Schiff bases and coordination complexes with transition metals, which find application in catalysis and material science.

Safety data indicate that 4‑benzylaminobenzene is moderately toxic upon ingestion and may cause irritation to the skin, eyes, and respiratory tract. It should be handled with appropriate personal protective equipment, and its use should be confined to well‑ventilated areas or fume hoods. The compound is considered non‑carcinogenic under standard laboratory exposure conditions.