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Merck

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:
80-73-9
Molecular Weight:
114.15
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
57650015
EC Number:
201-304-8
Beilstein/REAXYS Number:
108808
MDL number:
MFCD00003188
Assay:
≥99.0% (GC)
Form:
liquid

Key Documents

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InChI

1S/C5H10N2O/c1-6-3-4-7(2)5(6)8/h3-4H2,1-2H3

assay

≥99.0% (GC)

form

liquid

Quality Level

200

bp

224-226 °C (lit.)

solubility

toluene: soluble(lit.), water: miscible

density

1.056 g/mL at 25 °C (lit.)

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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.

signalword

Danger

flash_point_f

219.2 °F - closed cup

flash_point_c

104 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Repr. 1B

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF8138V
SDBB7622
WXBF7750V
SDBB5027
SDBB5169

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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)
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)
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
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
Yolanda T Chong et al.
Cell, 161(6), 1413-1424 (2015-06-06)
Proteomics has proved invaluable in generating large-scale quantitative data; however, the development of systems approaches for examining the proteome in vivo has lagged behind. To evaluate protein abundance and localization on a proteome scale, we exploited the yeast GFP-fusion collection
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