1,3-Dimethyl-2-imidazolidinone

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.

1,3-Dimethyl-2-imidazolidinone

Names
Preferred IUPAC name 1,3-Dimethylimidazolidin-2-one
Other names Dimethylethyleneurea N,N′-Dimethylimidazolidinone
Identifiers
CAS Number	80-73-9 Y
3D model (JSmol)	Interactive image Interactive image
Abbreviations	DMI
ChEMBL	ChEMBL12338 Y
ChemSpider	6409 Y
ECHA InfoCard	100.001.187
PubChem CID	6661
UNII	5C1YQQ9M90 Y
CompTox Dashboard (EPA)	DTXSID1073153
InChI InChI=1S/C5H10N2O/c1-6-3-4-7(2)5(6)8/h3-4H2,1-2H3 Y Key: CYSGHNMQYZDMIA-UHFFFAOYSA-N Y InChI=1/C5H10N2O/c1-6-3-4-7(2)5(6)8/h3-4H2,1-2H3 Key: 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[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). Y verify (what is YN ?) Infobox references

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]}