1,3-Dimethyl-2-imidazolidinone
Chemical compound
From Wikipedia, the free encyclopedia
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.
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| Names | |||
|---|---|---|---|
| Preferred IUPAC name
1,3-Dimethylimidazolidin-2-one | |||
| Other names
Dimethylethyleneurea N,Nâ²-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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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.[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-dimethyliminazolid-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
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]
DMI is toxic in contact with skin.[12] [dubious â discuss]