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Merck

40725

1,3-Dimethyl-2-imidazolidinone

absolute, over molecular sieve (H2O ≤0.04%), ≥99.5% (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:
57650014
EC Number:
201-304-8
Beilstein/REAXYS Number:
108808
MDL number:
MFCD00003188

Product Name

1,3-Dimethyl-2-imidazolidinone, absolute, over molecular sieve (H2O ≤0.04%), ≥99.5% (GC)

InChI key

CYSGHNMQYZDMIA-UHFFFAOYSA-N

InChI

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

SMILES string

CN1CCN(C)C1=O

grade

absolute

assay

≥99.5% (GC)

form

liquid

quality

over molecular sieve (H2O ≤0.04%)

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.)

Quality Level

200

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Other Notes

Solvent used in various synthetic organic transformations. Studied in the formation of functionally stabilized hydrosilanediyl-transition metal complexes produced photochemically from arylsilanes.
Aprotic, dipolar solvent which often can be used as a substitute for the carcinogenic HMPA

Application

1,3-Dimethyl-2-imidazolidinone may be used:
  • As substitute solvent for HMPA in the synthesis of 1,2-bis(trimethylsilyl)benzene.
  • As solvent during the α-regioselective prenylation of imines.
  • A component of mobile phase during size-exclusion chromatographic analysis of cellulose.

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.

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Danger

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Repr. 2

Storage Class

10 - Combustible liquids

wgk

WGK 2

flash_point_f

219.2 °F - closed cup

flash_point_c

104 °C - closed cup

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
SDBB5027
SDBB5169
SDBB2284
STBL4155
STBL1141

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D. Seebach et al.
Chemische Berichte, 115, 1705-1705 (1982)
U. Schollkopf et al.
Synthesis, 675-675 (1983)
T. Mukaiyama et al.
Chemistry Letters (Jpn), 1507-1507 (1980)
C.J. Gilmore et al.
Tetrahedron Letters, 24, 3269-3269 (1983)
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)
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