1,3-Dimethyl-2-imidazolidinone
Title: 1,3-Dimethyl-2-imidazolidinone
CAS Registry Number: 80-73-9
Additional Names: N,N¢-Dimethylethyleneurea; DMI
Molecular Formula: C5H10N2O
Molecular Weight: 114.15
Percent Composition: C 52.61%, H 8.83%, N 24.54%, O 14.02%
Literature References: Aprotic basic solvent. Prepn: W. R. Boon, J. Chem. Soc. 1947, 307; M. W. Farlow, US 2422400 (1947 to du Pont); E. V. Dehmlow, Y. R. Rao, Synth. Commun. 18, 487 (1988). Prepn and pharmacological activity: E. J. Lien, W. D. Kumler, J. Med. Chem. 11, 214 (1968). Prepn and spectral properties: H. Kohn et al., J. Org. Chem. 42, 941 (1977). Evaluation as replacement solvent for HMPA, q.v.: C.-C. Lo, P.-M. Chao, J. Chem. Ecol. 16, 3245 (1990).
Properties: mp 8.2° (Dehmlow, Rao); also reported as mp below -4° (Lo, Chao). bp754 220°. bp17 106-108°. bp2 67-68°. nD20 1.4720. d25 1.0519 g/ml. Dipole moment (dioxane, benzene): 4.09 ±0.01 D, 4.05 ±0.01 D. Dielectric constant (25°): 37.6. Viscosity (25°): 1.944 cP. Soly in toluene: >5%. LD50 i.p. in mice: 2840 mg/kg (Lien).
Melting point: mp 8.2° (Dehmlow, Rao); mp below -4° (Lo, Chao)
Boiling point: bp754 220°; bp17 106-108°; bp2 67-68°
Index of refraction: nD20 1.4720
Density: d25 1.0519 g/ml
Toxicity data: LD50 i.p. in mice: 2840 mg/kg (Lien)
Use: As substitute solvent for HMPA in organic synthesis.

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