Chemistry:1,3-Dimethyl-2-imidazolidinone

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1,3-Dimethyl-2-imidazolidinone (DMI) is a cyclic urea used as a high-boiling polar aprotic solvent.[1] This colourless, highly polar solvent has high thermal and chemical stability. Together with homologous solvent DMPU, since the 1970s it serves as an analog of tetramethylurea.[2][3] It can be prepared from 1,2-dimethylethylenediamine by reaction with phosgene.

History

In 1940 Du Pont applied for a patent on acetylene storage in many polar organic solvents, one of which was 1,3-dimethyl-2-imid azolidone.[4] The company filed another patent on a method of synthesizing the same compound, albeit called s-dimethylethyleneurea, in 1944.[5]

Soon thereafter William Boon from the Imperial Chemical Industries published a different synthesis method of what he called 1:3-dimethyliminazolid-2-one.[6] The compound was more closely studied in the 1960s,[7][8][9] with its adoption as a solvent starting in the 1970s.[3]

Solvent

DMI has excellent solvating ability for both inorganic and organic compounds. In many applications,[citation needed] DMI (as well as DMPU) can be used as a substitute or replacement for the carcinogenic solvent HMPA.[10] Compared to the 6-atom ring analog, it has an advantage of lower viscosity (1.9 vs. 2.9 cP at 25°C).[3]


References

  1. ↑ Leahy, Ellen M. "1,3-Dimethyl-2-imidazolidinone" e-EROS Encyclopedia of Reagents for Organic Synthesis (2001),doi:10.1002/047084289X.rd342
  2. ↑ Rosenfarb, Joseph; Huffman, Hugh L. Jr.; Caruso, Joseph A. (1976). "Dielectric constants, viscosities, and related physical properties of several substituted liquid ureas at various temperatures". Journal of Chemical & Engineering Data 21 (2): 150–153. doi:10.1021/je60069a034. ISSN 0021-9568. https://pubs.acs.org/doi/10.1021/je60069a034. 
  3. ↑ 3.0 3.1 3.2 Barker, Barbara J.; Rosenfarb, Joseph; Caruso, Joseph A. (1979). "Ureas as Solvents for Chemical Investigations" (in en). Angewandte Chemie International Edition in English 18 (7): 503–507. doi:10.1002/anie.197905031. ISSN 1521-3773. https://www.academia.edu/114612084. 
  4. ↑ U.S. Patent 2,405,693
  5. ↑ U.S. Patent 2,422,400
  6. ↑ Boon, W. R. (1947). "Respiratory stimulants. Part I. Fully-substituted ureas derived from αω-alkylenediamines" (in en). Journal of the Chemical Society (Resumed): 307–318. doi:10.1039/JR9470000307. ISSN 0368-1769. https://pubs.rsc.org/en/content/articlelanding/1947/jr/jr9470000307. 
  7. ↑ Zaugg, Harold E. (1960). "Specific Solvent Effects in the Alkylation of Enolate Anions. IV. Kinetic Order of Solvent Participation" (in EN). Journal of the American Chemical Society 83 (4): 837–840. doi:10.1021/ja01465a025. https://pubs.acs.org/doi/pdf/10.1021/ja01465a025. Retrieved 2025-01-18. 
  8. ↑ Lien, Eric J. (1966) (in en). Dipole Moment, Structure and Activity of Cyclic Ureas, Thioureas and Related Compounds. University of California, San Francisco. https://books.google.com/books?id=UTdolpPC8o8C&q=dimethylethyleneurea. 
  9. ↑ Ulrich, Henri (1968), Ulrich, Henri, ed., "Cyclic Imidoyl Halides" (in en), The Chemistry of Imidoyl Halides (New York, NY: Springer US): pp. 193–210, doi:10.1007/978-1-4684-8947-7_8, ISBN 978-1-4684-8947-7, https://link.springer.com/chapter/10.1007/978-1-4684-8947-7_8, retrieved 2025-01-18 
  10. ↑ Lo, C.-C.; Chao, P.-M. (1990). "Replacement of carcinogenic solvent HMPA by DMI in insect sex pheromone synthesis". Journal of Chemical Ecology 16 (12): 3245–3253. doi:10.1007/BF00982095. PMID 24263426. Bibcode: 1990JCEco..16.3245L. 



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