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Updated: Feb 5, 2026
Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
A structural study of 2,4-di-methyl-aniline derivatives
Samuel C Penner1, Maryam Kalvandi1, Jamie S Ritch1
1Department of Chemistry, The University of Winnipeg, Winnipeg MB R3B 2E9, Canada.
Abstract:
Crystallographic studies of nitro-gen-containing small mol-ecules aid in the elucidation of their structure-activity relationships and modes of aggregation. In this study, two previously synthesized mol-ecules are crystallographically characterized for the first time. Reaction of 2,4-di-methyl-aniline with N-bromo-succinimide affords the ortho-brominated derivative 2-bromo-4,6-di-methyl-aniline (1; C8H10BrN), which sublimates in vacuo to afford crystals featuring hydrogen-bonded chains as well as Type I halogen-halogen inter-actions. Conversely, alkyl-ation of two equivalents of 2,4-di-methyl-aniline with 1,2-di-bromo-ethane affords a separable mixture of N,N'-bis-(2,4-di-methyl-phen-yl)piperazine (2; C20H26N2), which was crystallographically characterized, as well as N,N'-bis-(2,4-di-methyl-phen-yl)ethyl-enedi-amine (3).
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