1,3-Dimethyl-2-imidazolidinone

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1,3-Dimethyl-2-imidazolidinone
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Abbreviations DMI
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Template:Longitem C5H10N2O
Molar mass 114.1457
Appearance colorless liquid
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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

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,Script error: No such module "Unsubst". 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.Script error: No such module "Unsubst".

DMI is toxic in contact with skin.[12] Script error: No such module "Unsubst".

References

  1. ↑ DMI at Mitsui Chemicals
  2. ↑ Leahy, Ellen M. "1,3-Dimethyl-2-imidazolidinone" e-EROS Encyclopedia of Reagents for Organic Synthesis (2001),Script error: No such module "CS1 identifiers".
  3. ↑ Script error: No such module "Citation/CS1".
  4. ↑ a b c Script error: No such module "Citation/CS1".
  5. ↑ U.S. patent 2405693
  6. ↑ U.S. patent 2422400
  7. ↑ Script error: No such module "Citation/CS1".
  8. ↑ Script error: No such module "citation/CS1".
  9. ↑ Script error: No such module "citation/CS1".
  10. ↑ Script error: No such module "citation/CS1".
  11. ↑ Script error: No such module "Citation/CS1".
  12. ↑ DMI at TCI
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