1,3-Dimethyl-2-imidazolidinone
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| Names | |||
|---|---|---|---|
| Preferred IUPAC name
1,3-Dimethylimidazolidin-2-one | |||
| Other names
Dimethylethyleneurea N,N′-Dimethylimidazolidinone | |||
| Identifiers | |||
3D model (JSmol) |
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| Abbreviations | DMI | ||
| ChEMBL | |||
| ChemSpider | |||
| ECHA InfoCard | 100.001.187 | ||
PubChem CID |
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| UNII | |||
CompTox Dashboard (EPA) |
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| Properties | |||
| C5H10N2O | |||
| Molar mass | 114.1457 | ||
| Appearance | colorless liquid | ||
| Melting point | 8.2[1] °C (46.8 °F; 281.3 K) | ||
| Boiling point | 225 °C (437 °F; 498 K) | ||
| Hazards | |||
| Flash point | 120 °C (248 °F; 393 K) | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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1,3-Dimethyl-2-imidazolidinone (DMI) is a cyclic urea used as a high-boiling polar aprotic solvent.[2] 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.[3][4] It can be prepared from 1,2-dimethylethylenediamine by reaction with phosgene.
History
[edit]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.[5] The company filed another patent on a method of synthesizing the same compound, albeit called s-dimethylethyleneurea, in 1944.[6]
Soon thereafter William Boon from the Imperial Chemical Industries published a different synthesis method of what he called 1:3-dimethyliminazolidine-2-one.[7] The compound was more closely studied in the 1960s,[8][9][10] with its adoption as a solvent starting in the 1970s.[4]
Solvent
[edit]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.[11] Compared to the 6-atom ring analog, it has an advantage of lower viscosity (1.9 vs. 2.9 cP at 25 °C).[4]
DMI is used in a variety of applications including detergents, dyestuffs, electronic materials and in the manufacture of polymers.[citation needed]
References
[edit]- ↑ DMI at Mitsui Chemicals
- ↑ Leahy, Ellen M. "1,3-Dimethyl-2-imidazolidinone" e-EROS Encyclopedia of Reagents for Organic Synthesis (2001),doi:10.1002/047084289X.rd342
- ↑ 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.
- 1 2 3 Barker, Barbara J.; Rosenfarb, Joseph; Caruso, Joseph A. (1979). "Ureas as Solvents for Chemical Investigations". Angewandte Chemie International Edition in English. 18 (7): 503–507. doi:10.1002/anie.197905031. ISSN 1521-3773.
- ↑ U.S. patent 2,405,693
- ↑ U.S. patent 2,422,400
- ↑ Boon, W. R. (1947). "Respiratory stimulants. Part I. Fully-substituted ureas derived from αω-alkylenediamines". Journal of the Chemical Society (Resumed): 307–318. doi:10.1039/JR9470000307. ISSN 0368-1769.
- ↑ Zaugg, Harold E. (1960). "Specific Solvent Effects in the Alkylation of Enolate Anions. IV. Kinetic Order of Solvent Participation". Journal of the American Chemical Society. 83 (4): 837–840. doi:10.1021/ja01465a025. Retrieved 2025-01-18.
- ↑ Lien, Eric J. (1966). Dipole Moment, Structure and Activity of Cyclic Ureas, Thioureas and Related Compounds. University of California, San Francisco.
- ↑ Ulrich, Henri (1968), "Cyclic Imidoyl Halides", in Ulrich, Henri (ed.), 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, retrieved 2025-01-18
- ↑ 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. Bibcode:1990JCEco..16.3245L. doi:10.1007/BF00982095. PMID 24263426. S2CID 9859086.
- ↑ DMI at TCI