4Vinylbenzylamine

4-Vinylbenzylamine, also called para-vinylbenzylamine, is an organic compound featuring a benzene ring substituted at the para position by a vinyl group (-CH=CH2) and by a benzylamine group (-CH2-NH2). Its formula is C9H11N, and the molecule combines a primary amine with a vinyl moiety, enabling both amine chemistry and vinyl polymerization. It is typically a colorless to pale liquid with the characteristic odor of amines and is soluble in many organic solvents; it can form salts with acids, increasing its water compatibility in salt form.

Synthesis of 4-vinylbenzylamine is usually approached by introducing a benzylamine side chain onto a para-vinyl-substituted benzene or by reductive amination strategies that install the -CH2NH2 group onto a para-vinyl precursor. Routes reported in the literature generally rely on functionalizing a suitable para-substituted benzene framework to install the benzylic amine while preserving the vinyl functionality for subsequent reactivity.

Applications of 4-vinylbenzylamine center on its dual functionality. The vinyl group allows copolymerization with styrene, acrylates, or other vinyl monomers to form crosslinked or functional polymers, while the amine group provides a handle for further derivatization, such as amidation, urea formation, or ligand attachment. As such, it serves as a reactive intermediate in organic synthesis and polymer chemistry.

Safety handling involves standard precautions for amines and vinyl monomers: use in a well-ventilated area, wear appropriate PPE, and store away from oxidizers and potential polymerization initiators. Aromatic vinyl compounds can be reactive, so inhibitors may be used for storage.