1,3-Dimethyl-2-imidazolidinone
[CAS# 80-73-9]

Identification

• Classification: Analytical chemistry >> Analytical reagent >> Common analytical reagents
• Name: 1,3-Dimethyl-2-imidazolidinone
• Synonyms: N,N'-Dimethylethyleneurea; 1,3-Dimethylimidazolidin-2-one; DMEU; DMI
• Molecular Formula: C₅H₁₀N₂O
• Molecular Weight: 114.15
• CAS Registry Number: 80-73-9
• EC Number: 201-304-8
• SMILES: CN1CCN(C1=O)C

Properties

• Density: 1.057 g/mL (4 °C) (Expl.)
• Melting point: 8.2 °C (Expl.)
• Boiling point: 224-226 °C (Expl.)
• Refractive index: 1.472 (Expl.)
• Flash point: 93 °C (Expl.)
• Water solubility: freely soluble

Safety Data

• Hazard Symbols: GHS05;GHS06;GHS07;GHS08 Danger
• Risk Statements: H302-H311-H315-H318-H319-H361-H373
• Safety Statements: P203-P260-P262-P264-P264+P265-P270-P280-P301+P317-P302+P352-P305+P351+P338-P305+P354+P338-P316-P317-P318-P319-P321-P330-P332+P317-P337+P317-P361+P364-P362+P364-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Serious eye damage	Eye Dam.	1	H318
Reproductive toxicity	Repr.	2	H361
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	3	H311
Skin irritation	Skin Irrit.	2	H315
Reproductive toxicity	Repr.	2	H361fd
Skin corrosion	Skin Corr.	1B	H314
Acute toxicity	Acute Tox.	4	H312
Specific target organ toxicity - single exposure	STOT SE	2	H371
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H301
Specific target organ toxicity - single exposure	STOT SE	3	H336

• Transport Information: UN 2810

Discovery and Applications

1,3-Dimethyl-2-imidazolidinone, commonly abbreviated as DMI, is a highly polar, aprotic solvent that has found significant applications in organic synthesis and materials science. Its unique properties, including high thermal stability and excellent solvation capability, make it a valuable tool in chemical research and industrial processes.

DMI was first synthesized in the mid-20th century during studies on imidazolidinone derivatives. Researchers were exploring nitrogen-containing heterocyclic compounds for their potential use in solvents and intermediates. DMI emerged as a compound of interest due to its ability to dissolve a wide range of inorganic and organic substances, making it a versatile medium for chemical reactions.

The molecular structure of DMI features a five-membered imidazolidinone ring with two methyl groups attached to the nitrogen atoms. This configuration imparts high polarity to the molecule while maintaining low nucleophilicity. As a result, DMI can effectively stabilize ions and polar intermediates without participating in side reactions, which is critical in reactions such as nucleophilic substitutions and metal-catalyzed transformations.

DMI's utility extends to the synthesis of advanced materials, including polymers, resins, and composite materials. Its ability to dissolve challenging precursors enables the preparation of high-performance materials used in electronics, coatings, and adhesives. Additionally, DMI is employed as a co-solvent in lithium-ion battery electrolytes, where its stability and ionic conductivity enhance battery performance.

In organic synthesis, DMI is widely used in reactions involving strong nucleophiles or bases, such as the synthesis of aryl ethers and amides. It has also been employed in peptide coupling reactions, where its ability to stabilize intermediates leads to improved yields. Furthermore, DMI serves as a solvent in the production of pharmaceuticals, agrochemicals, and dyes, highlighting its versatility across various industries.

The environmental and safety aspects of DMI have also been studied extensively. While it is considered a relatively safe solvent compared to some traditional options, proper handling and disposal are necessary to minimize its ecological impact. Ongoing research focuses on developing greener alternatives or improving the recyclability of DMI to enhance its sustainability.

As a solvent with a broad range of applications, DMI continues to be a subject of scientific interest. Its role in facilitating complex chemical transformations and enabling the development of new materials underscores its importance in modern chemistry. Researchers are actively exploring new methods to optimize its use and expand its applications, ensuring that DMI remains a cornerstone of chemical innovation.

References

2024. Theoretical and experimental studies on the electrodeposition of magnesium in 1,3-dimethyl-2-imidazolidinone organic solvent at room temperature. Ionics, 30(8).
DOI: 10.1007/s11581-024-05597-z

2023. Study on synthesis of ursodeoxycholic acid by reduction of 7-ketolithocholic acid in double aprotic solvents and molecular simulations. Bioresources and Bioprocessing, 10(1).
DOI: 10.1186/s40643-023-00668-x

2023. Harnessing triaryloxonium ions for aryne generation. Nature Synthesis, 3(1).
DOI: 10.1038/s44160-023-00408-1