Skip to Content
Merck
All Photos(3)

Key Documents

View All Documentation

40727

Sigma-Aldrich

1,3-Dimethyl-2-imidazolidinone

≥99.0% (GC)

Synonym(s):

N,N′-Dimethylethyleneurea, DMEU, DMI

Sign Into View Organizational & Contract Pricing
All Photos(3)

About This Item

Empirical Formula (Hill Notation):
C5H10N2O
CAS Number:
80-73-9
Molecular Weight:
114.15
Beilstein:
108808
EC Number:
201-304-8
MDL number:
MFCD00003188
UNSPSC Code:
12352005
PubChem Substance ID:
57650015
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

200

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

Looking for similar products? Visit Product Comparison Guide

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.[1] Conversion of CO2 to form lower alcohols by homogeneous catalytic hydrogenation using DMI as solvent has been investigated.[2]

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.[3]
  • As solvent during the α-regioselective prenylation of imine.[4]
  • As component of mobile phase for the size-exclusion chromatographic analysis of cellulose.[5]

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

H302,H318,H361fd

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
SDBB2284
STBL4155
MKCV6872
MKCV8685
STBL1141

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
Highly selective hydrogenation of CO2 into C2+ alcohols by homogeneous catalysis.
Qian Q, et al.
Chemical Science, 6(10), 5685-5689 (2015)
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
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)
View All Related Papers

Questions

1–2 of 2 Questions  

  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

      Helpful?

  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

      Helpful?

Reviews

No rating value

Active Filters

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service