The reaction of o-and p-halogen-substituted phenols with formaldehyde and representative primary aliphatic amines was studied. The number of halogen substituents on the phenol and the specific amine used were found to be important factors in determining both the course of the condensation and the stability of the benzoxazines, which were obtained with substituted N, N-bis (hydroxybenzy1) amines and substituted 2-aminomethylphenols.