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1,3-Dimethyl-2-imidazolidinone

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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
CAS Number
3D model (JSmol)
Abbreviations DMI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.187 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H10N2O/c1-6-3-4-7(2)5(6)8/h3-4H2,1-2H3Key: CYSGHNMQYZDMIA-UHFFFAOYSA-N
  • InChI=1/C5H10N2O/c1-6-3-4-7(2)5(6)8/h3-4H2,1-2H3Key: CYSGHNMQYZDMIA-UHFFFAOYAB
SMILES
  • O=C1N(C)CCN1C
  • CN1CCN(C1=O)C
Properties
Chemical formula C5H10N2O
Molar mass 114.1457
Appearance colorless liquid
Melting point 8.2 °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 , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

1,3-Dimethyl-2-imidazolidinone (DMI) is a cyclic urea used as a high-boiling polar aprotic solvent. 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. 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. The company filed another patent on a method of synthesizing the same compound, albeit called s-dimethylethyleneurea, in 1944.

Soon thereafter William Boon from the Imperial Chemical Industries published a different synthesis method of what he called 1:3-dimethyliminazolid-2-one. The compound was more closely studied in the 1960s, 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, DMI (as well as DMPU) can be used as a substitute or replacement for the carcinogenic solvent HMPA. 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.

DMI is toxic in contact with skin.

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. 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.
  4. ^ 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.
  5. U.S. patent 2,405,693
  6. U.S. patent 2,422,400
  7. Boon, W. R. (1947). "Respiratory stimulants. Part I. Fully-substituted ureas derived from αω-alkylenediamines". Journal of the Chemical Society (Resumed) (0): 307–318. doi:10.1039/JR9470000307. ISSN 0368-1769.
  8. Zaugg, Harold E. (1960). "Specific Solvent Effects in the Alkylation of Enolate Anions. IV. Kinetic Order of Solvent Participation". ACS Publications. doi:10.1021/ja01465a025. Retrieved 2025-01-18.
  9. Lien, Eric J. (1966). Dipole Moment, Structure and Activity of Cyclic Ureas, Thioureas and Related Compounds. University of California, San Francisco.
  10. Ulrich, Henri (1968), Ulrich, Henri (ed.), "Cyclic Imidoyl Halides", 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
  11. 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.
  12. DMI at TCI
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