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  $\ce{C_6H_5NH_2 + 3Cl_2 -&gt; C_6H_2NH_2 Cl_3 + 3HCl}$ happen?
Chlorination of aniline with chlorine is rapid and gives 2,4,6-trichloroaniline according to the references cited in this paper here. The earliest reference cited is 1845 by AW Hofmann so it has been around a long time. More modern approaches use N-Chlorosuccinimide as the reaction is more controllable