Abstract
Hexamethylphosphoric triamide (HMPA) is a good solvent for the alkylation of terminal acetylenes; however, it has been proven to be a carcinogen towards rats and should be considered as a serious risk to man when a large-scale synthesis is involved. Thus the search for a safe alternative is important. The physical properties of 1,3-dimethyl-2-imidazolidinone (DMI) are similar to DMPU (1,3-dimethyl-2-oxo-hexahydropyrimidine) and HMPA, but the potential toxicological risk of DMI is less than DMPU and HMPA. When used in the alkylation of terminal acetylenes, DMI is comparable with HMPA, thus it is a good alternative solvent to the carcinogen HMPA in the alkylation because it provides a safer working environment than DMPU and HMPA.
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Lo, C.C., Chao, P.M. Replacement of carcinogenic solvent HMPA by DMI in insect sex pheromone synthesis. J Chem Ecol 16, 3245–3253 (1990). https://doi.org/10.1007/BF00982095
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DOI: https://doi.org/10.1007/BF00982095