40727
1,3-Dimethyl-2-imidazolidinone
≥99.0% (GC)
Synonym(s):
N,N′-Dimethylethyleneurea, DMEU, DMI
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About This Item
Empirical Formula (Hill Notation):
C5H10N2O
CAS Number:
Molecular Weight:
114.15
Beilstein:
108808
EC Number:
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
Assay
≥99.0% (GC)
form
liquid
refractive index
n20/D 1.472 (lit.)
bp
224-226 °C (lit.)
solubility
toluene: soluble(lit.)
water: miscible
density
1.056 g/mL at 25 °C (lit.)
SMILES string
CN1CCN(C)C1=O
InChI
1S/C5H10N2O/c1-6-3-4-7(2)5(6)8/h3-4H2,1-2H3
InChI key
CYSGHNMQYZDMIA-UHFFFAOYSA-N
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General description
1,3-Dimethyl-2-imidazolidinone (DMI) is an imidazolidine derivative. It is reported to act as a promoter by minimizing the formation of dialkylation byproducts and accelerating the rate of monoalkylation of γ-butyrolactone. Conversion of CO2 to form lower alcohols by homogeneous catalytic hydrogenation using DMI as solvent has been investigated.
Application
1,3-Dimethyl-2-imidazolidinone may be used:
- As substitute solvent for hexamethylphosphoric triamide (HMPA) in the synthesis of 1,2-bis(trimethylsilyl)benzene.
- As solvent during the α-regioselective prenylation of imine.
- As component of mobile phase for the size-exclusion chromatographic analysis of cellulose.
Other Notes
Solvent used in various synthetic organic transformations. Studied in the formation of functionally stabilized hydrosilanediyl-transition metal complexes produced photochemically from arylsilanes.
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 4 Oral - Eye Dam. 1 - Repr. 2
Storage Class Code
10 - Combustible liquids
WGK
WGK 2
Flash Point(F)
219.2 °F - closed cup
Flash Point(C)
104 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Case Study of a γ-Butyrolactone Alkylation with 1,3-Dimethyl-2-imidazolidinone as a Promoter.
Li B, et al.
Organic Process Research & Development, 5(6), 609-611 (2001)
Tsugio Kitamura et al.
The Journal of organic chemistry, 78(7), 3421-3424 (2013-03-20)
A practical and safe synthesis of 1,2-bis(trimethylsilyl)benzene from 1,2-dichlorobenzene and Me3SiCl was achieved by use of a hybrid metal of Mg and CuCl in the presence of LiCl in 1,3-dimethyl-2-imidazolidinone (DMI). This method does not require a toxic HMPA, provides
Li-Ming Zhao et al.
Organic letters, 14(3), 886-889 (2012-01-24)
A highly α-regioselective prenylation of imines has been successfully developed. The efficiency of this approach is confirmed by a wide range of imines including N- and C-aryl aldimines, N-alkyl aldimines, C-alkyl aldimines, and N- and C-aryl ketimines. The approach uses
SEC-MALLS analysis of cellulose using LiCl/1, 3-dimethyl-2-imidazolidinone as an eluent.
Yanagisawa M, et al.
Cellulose, 11(2), 169-176 (2004)
Jose Maria Carvajal-Gonzalez et al.
Nature communications, 6, 6751-6751 (2015-04-08)
A key step in generating planar cell polarity (PCP) is the formation of restricted junctional domains containing Frizzled/Dishevelled/Diego (Fz/Dsh/Dgo) or Van Gogh/Prickle (Vang/Pk) complexes within the same cell, stabilized via Flamingo (Fmi) across cell membranes. Although models have been proposed
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