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1,3-Dimethyl-2-imidazolidinone

From Wikipedia, the free encyclopedia
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)
AbbreviationsDMI
ChEMBL
ChemSpider
ECHA InfoCard100.001.187Edit this at Wikidata
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 mass114.1457
Appearancecolorless liquid
Melting point8.2[1] °C (46.8 °F; 281.3 K)
Boiling point225 °C (437 °F; 498 K)
Hazards
Flash point120 °C (248 °F; 393 K)
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Chemical compound

1,3-Dimethyl-2-imidazolidinone (DMI) is a cyclicurea used as a high-boilingpolar aproticsolvent.[2] This colourless, highly polar solvent has high thermal and chemical stability. Together withhomologous solventDMPU, since the 1970s it serves as an analog oftetramethylurea.[3][4] It can be prepared from1,2-dimethylethylenediamine by reaction withphosgene.

History

[edit]

In 1940Du Pont applied for a patent onacetylene storage in many polar organic solvents, one of which was1,3-dimethyl-2-imid azolidone.[5] The company filed another patent on a method of synthesizing the same compound, albeit calleds-dimethylethyleneurea, in 1944.[6]

Soon thereafterWilliam Boon from theImperial Chemical Industries published a different synthesis method of what he called1:3-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

[edit]

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 solventHMPA.[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][dubiousdiscuss]

References

[edit]
  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. ^abcBarker, 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. Retrieved2025-01-18.
  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, retrieved2025-01-18
  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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