# Reaction between phenylamine and halogens

I understand that phenylamine is considerably more reactive than benzene, meaning that it is able to react with bromine water to give 2,3,6-tribromophenylamine. But I was then wondering why I haven't seen anywhere mention reactions with other halogens. So will phenylamine react with other halogens to produce a similar compound, I see no reason why it wouldn't happen? Do text books just use bromine water as it is convenient?

Will $$\ce{C_6H_5NH_2 + 3Cl_2 -> C_6H_2NH_2 Cl_3 + 3HCl}$$ happen?

• Why would you get N,N-Dichloroaniline instead? and would iodine do the same? Why isn't bromine behaving in this way? – H.Linkhorn Mar 12 at 20:12
• @user55119 Yeah, redox would happen, but this product is unlikely. – Mithoron Mar 12 at 20:14
• It's aniline's ring that is easily oxidated, not nitrogen. – Mithoron Mar 12 at 20:16