A structural study of 2,4-di­methyl­aniline derivatives

Crystallographic studies of nitro­gen-containing small mol­ecules aid in the elucidation of their structure–activity relationships and modes of aggregation. In this study, two previously synthesized mol­ecules are crystallographically characterized for the first time. Reaction of 2,4-di­methyl­aniline with N-bromo­succinimide affords the ortho-brominated derivative 2-bromo-4,6-di­methyl­aniline (1; C(8)H(10)BrN), which sublimates in vacuo to afford crystals featuring hydrogen-bonded chains as well as Type I halogen–halogen inter­actions. Conversely, alkyl­ation of two equivalents of 2,4-di­methyl­aniline with 1,2-di­bromo­ethane affords a separable mixture of N,N′-bis­(2,4-di­methyl­phen­yl)piperazine (2; C(20)H(26)N(2)), which was crystallographically characterized, as well as N,N′-bis­(2,4-di­methyl­phen­yl)ethyl­enedi­amine (3).