1,3-Dimethyl-2-imidazolidinone

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1,3-Dimethyl-2-imidazolidinone
Dimethylimidazolidinone.png
1,3-Dimethyl-2-imidazolidinone 3D ball.png
Names
Preferred IUPAC name
1,3-Dimethylimidazolidin-2-one
Other names
Dimethylethyleneurea
N,N′-Dimethylimidazolidinone
Identifiers
3D model (JSmol)
AbbreviationsDMI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.187 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C5H10N2O/c1-6-3-4-7(2)5(6)8/h3-4H2,1-2H3 Yes check.svgY
    Key: CYSGHNMQYZDMIA-UHFFFAOYSA-N Yes check.svgY
  • 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
Appearancecolorless 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.

Contents

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 – discuss ]

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. 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.
  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): 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". Journal of the American Chemical Society. 83 (4): 837–840. 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. Bibcode:1990JCEco..16.3245L. doi:10.1007/BF00982095. PMID   24263426. S2CID   9859086.
  12. ↑ DMI at TCI
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