1,3-Dimethyl-2-imidazolidinone

changed 477205297 Dimethylimidazolidinone.png 120px Structural formula of 1,3-dimethyl-2-imidazolidinone 1,3-Dimethyl-2-imidazolidinone 3D ball.png 135 Ball-and-stick model of the 1,3-dimethyl-2-imidazolidinone molecule 1,3-Dimethylimidazolidin-2-one DimethylethyleneureaN,N-Dimethylimidazolidinone DMI correct chemspider 6409 1/C5H10N2O/c1-6-3-4-7(2)5(6)8/h3-4H2,1-2H3 CYSGHNMQYZDMIA-UHFFFAOYAB CN1CCN(C1=O)C correct EBI 12338 correct chemspider 1S/C5H10N2O/c1-6-3-4-7(2)5(6)8/h3-4H2,1-2H3 correct chemspider CYSGHNMQYZDMIA-UHFFFAOYSA-N correct CAS 80-73-9 correct FDA 5C1YQQ9M90 6661 O=C1N(C)CCN1C C5H10N2O 114.1457 colorless liquid 8.2DMI at Mitsui Chemicals 225 120 1,3-Dimethyl-2-imidazolidinone (DMI) is a cyclic urea used as a high-boiling polar aprotic solvent.Leahy, Ellen M. "1,3-Dimethyl-2-imidazolidinone" e-EROS Encyclopedia of Reagents for Organic Synthesis (2001),10.1002/047084289X.rd342 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.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 https://pubs.acs.org/doi/10.1021/je60069a034 Journal of Chemical & Engineering Data 21 2 150–153 10.1021/je60069a034 0021-9568 subscription Barker Barbara J. Rosenfarb Joseph Caruso Joseph A. 1979 Ureas as Solvents for Chemical Investigations https://www.academia.edu/114612084 Angewandte Chemie International Edition in English en 18 7 503–507 10.1002/anie.197905031 1521-3773 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-imidazolidone.2405693 The company filed another patent on a method of synthesizing the same compound, albeit called s-dimethylethyleneurea, in 1944.2422400 Soon thereafter William Boon from the Imperial Chemical Industries published a different synthesis method of what he called 1:3-dimethyliminazolidine-2-one.Boon W. R. 1947 Respiratory stimulants. Part I. Fully-substituted ureas derived from αω-alkylenediamines https://pubs.rsc.org/en/content/articlelanding/1947/jr/jr9470000307 Journal of the Chemical Society (Resumed) en 307–318 10.1039/JR9470000307 0368-1769 subscription The compound was more closely studied in the 1960s,Zaugg Harold E. 1960 Specific Solvent Effects in the Alkylation of Enolate Anions. IV. Kinetic Order of Solvent Participation https://pubs.acs.org/doi/pdf/10.1021/ja01465a025 2025-01-18 Journal of the American Chemical Society 83 4 837–840 EN 10.1021/ja01465a025 subscription Lien Eric J. https://books.google.com/books?id=UTdolpPC8o8C&q=dimethylethyleneurea Dipole Moment, Structure and Activity of Cyclic Ureas, Thioureas and Related Compounds 1966 University of California, San Francisco enUlrich Henri Cyclic Imidoyl Halides 1968 The Chemistry of Imidoyl Halides 193–210 Ulrich Henri https://link.springer.com/chapter/10.1007/978-1-4684-8947-7_8 2025-01-18 New York, NY Springer US en 10.1007/978-1-4684-8947-7_8 978-1-4684-8947-7 subscription with its adoption as a solvent starting in the 1970s. Solvent DMI has excellent solvating ability for both inorganic and organic compounds. In many applications,January 2025 DMI (as well as DMPU) can be used as a substitute or replacement for the carcinogenic solvent HMPA.Lo, C.-C. Chao, P.-M. Replacement of carcinogenic solvent HMPA by DMI in insect sex pheromone synthesis Journal of Chemical Ecology 1990 16 12 3245–3253 10.1007/BF00982095 24263426 1990JCEco..16.3245L 9859086 Compared to the 6-atom ring analog, it has an advantage of lower viscosity (1.9 vs. 2.9 cP at 25 °C). DMI is used in a variety of applications including detergents, dyestuffs, electronic materials and in the manufacture of polymers.October 2016 DMI is toxic in contact with skin.DMI at TCI August 2023 References Category:Solvents Category:Amide solvents Category:Imidazolidinones Category:Methyl compounds