Title of project

The Three-Step Green Synthesis of 2, 6-Dinitro-4-methylaniline from p-Toluidine

Faculty Advisor

Dr. James Wollack

Department

Chemistry

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The Three-Step Green Synthesis of 2, 6-Dinitro-4-methylaniline from p-Toluidine

P-Toluidine was made into 2, 6-dinitro-4-methylaniline in a three step synthesis. P-Toluidine is toxic and possibly carcinogenic. 2, 6-dinitro-4-methylaniline is a compound of medical interest that had herbicidal use. First p-toluidine was tosylated using tosyl chloride. The tosylated product was then dinitrated using the amide from step one. Finally the dinitrated product was hydrolyzed to yield 2, 6-dinitro-4-methylaniline. After each step the product was purified by recrystallization and analyzed by melting point, IR, and NMR. Because some chemicals in this synthesis could be harmful, green chemistry was implemented to conduct a safer synthesis. H2SO2 was replaced with a different chemical which is cheaper and less toxic. This synthesis is important because it uses green chemistry practices to convert a toxic compound, p-toluidine, into a safer more useful compound.