1,3-Dimethyl-2-imidazolidinone

1,3-Dimethyl-2-imidazolidinone (DMI) is a cyclic urea used as a high-boiling polar aprotic solvent.[2] It is colourless, highly polar solvent has high thermal and chemical stability. It is a homolog of the related solvent DMPU. It can be prepared from 1,2-dimethylethylenediamine by reaction with phosgene.

1,3-Dimethyl-2-imidazolidinone
Structural formula of 1,3-dimethyl-2-imidazolidinone
Ball-and-stick model of the 1,3-dimethyl-2-imidazolidinone molecule
Names
Preferred IUPAC name
1,3-Dimethylimidazolidin-2-one
Other names
Dimethylethyleneurea
N,N′-Dimethylimidazolidinone
Identifiers
3D model (JSmol)
Abbreviations DMI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.187
UNII
  • InChI=1S/C5H10N2O/c1-6-3-4-7(2)5(6)8/h3-4H2,1-2H3 checkY
    Key: CYSGHNMQYZDMIA-UHFFFAOYSA-N checkY
  • InChI=1/C5H10N2O/c1-6-3-4-7(2)5(6)8/h3-4H2,1-2H3
    Key: CYSGHNMQYZDMIA-UHFFFAOYAB
  • O=C1N(C)CCN1C
  • CN1CCN(C1=O)C
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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Infobox references

Solvent

DMI has excellent solvating ability for both inorganic and organic compounds. In many applications, DMI (as well as DMPU) can be used as a substitute or replacement for the carcinogenic solvent HMPA.[3]

DMI is used in a variety of applications including detergents, dyestuffs, electronic materials and in the manufacture of polymers.

DMI is toxic in contact with skin.[4]

References
  1. DMI at Mitsui Chemicals
  2. Leahy, Ellen M. "1,3-Dimethyl-2-imidazolidinone" e-EROS Encyclopedia of Reagents for Organic Synthesis (2001),doi:10.1002/047084289X.rd342
  3. 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. S2CID 9859086.
  4. DMI at TCI
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