1,3-Dimethyl-2-imidazolidinone

• CAS: 80-73-9
• Catalog Number: ACM80739
• Category: Main Products
• Molecular Weight: 114.14
• Molecular Formula: C5H10N2O
• Description: 1,3-Dimethyl-2-imidazolidone, is a solvent used in various synthetic organic transformations. Studied in the formation of functionally stabilized hydrosilanediyl-transition metal complexes produced photochemically from arylsilanes.
• Synonyms: 1,3-DMI;karbomostsem;1,3-dimethylimidazolin-2-one;N,N’-dimethyl-2-imidazolidinone;rhonite1
• Boiling Point: 224-226 °C
• Melting Point: 8.2ºC
• Flash Point: 93ºC
• Density: 1.044
• Appearance: Clear liquid
• Hazard Codes: Xn
• HS Code: 2933399090
• LogP: -0.14060
• MDL Number: MFCD00003188
• PSA: 23.55
• Refractive Index: 1.471-1.473
• RIDADR: UN 2810
• WGK Germany: 3

Case Study

Film-Quality-Improving, Efficiency-Enhancing and Stability-Promoting Properties of 1,3-Dimethyl-2-imidazolidinone

Zhi, L. L., Li, Y. Q., Ci, L. J., & Wei, J. Q. Nanoscale Research Letters, 2017, 12, 632.

The chemical properties and functional effects of 1,3-dimethyl-2-imidazolidinone (DMI), an environmentally friendly aprotic polar additive, were studied using perovskite solar cell (PSC) fabrication and photovoltaic performance assays. The key functional characteristic is its strong Lewis base coordination with PbI₂ via carbonyl oxygen lone pairs, forming stable PbI₂·DMI adducts that govern nucleation, grain growth, and film quality in perovskite layers.
DMI exhibited significant perovskite film-quality-improving activity: adding 10 vol% DMI to the PbI₂/DMF precursor produced smooth, compact, and large-grained MAPbI₃ films, with average grain size increasing from 216 nm (100 °C annealing) to 375 nm (130 °C annealing). It demonstrated potent photovoltaic efficiency-enhancing effects: the optimized PSC yielded a power conversion efficiency (PCE) of 14.54%, with Jsc = 21.05 mA/cm², Voc = 1.02 V, and FF = 67.72%, representing a strong improvement over the DMI-free control (10.72% PCE). Additionally, DMI exerted charge-transport and stability-promoting properties: it reduced series resistance (Rs) from 26.16 Ω to 14.30 Ω, increased recombination resistance (Rrec) from 46.49 Ω to 2778 Ω, and accelerated electron transfer, as confirmed by photoluminescence quenching and time-resolved PL. Microstructural and electrochemical analyses confirmed reduced grain boundaries, suppressed charge recombination, and uniform crystalline morphology. These studies demonstrate that 1,3-dimethyl-2-imidazolidinone possesses significant film-quality-improving, efficiency-enhancing, and stability-promoting properties in perovskite solar cells.
The in vitro performance-enhancing effect was investigated in mesoscopic TiO₂/FTO-based perovskite solar cells using a modified two-step method. DMI was incorporated at 0, 10, and 20 vol% in PbI₂/DMF precursors; films were annealed at 100, 130, and 160 °C. Adduct formation was verified by FTIR, TGA, and XRD; morphology was characterized by SEM; photovoltaic metrics were measured under AM 1.5G illumination; charge dynamics were analyzed via impedance and PL spectroscopy. The results verified that DMI forms thermally stable Lewis adducts with PbI₂, slows uncontrolled crystallization, and enlarges perovskite grains, thereby boosting charge extraction and overall solar cell efficiency.

Concentration-Enhancing, Low-Loss and Scalable-Processing Properties of 1,3-Dimethyl-2-imidazolidinone

Abejón, R., Saidani, H., Deratani, A., Richard, C., & Sánchez-Marcano, J. Membranes, 2019, 9(12), 158.

The physicochemical properties and separation performance of 1,3-dimethyl-2-imidazolidinone (DMI) were studied using sweeping gas membrane distillation (SGMD) bench-scale and industrial-scale concentration assays. The key functional characteristic is its low volatility and high polarity, enabling efficient dehydration of aqueous DMI solutions with minimal solvent loss during membrane-based concentration.
DMI exhibited significant concentration-enhancing activity: aqueous DMI solutions were successfully concentrated from 30 wt% to 50 wt% within 9 hours using Liqui-Cel SuperPhobic® hollow-fiber membranes, with stable vapor flux maintained at approximately 0.11 kg/h·m². It demonstrated potent low-loss solvent-retaining effects: DMI permeation loss through the membrane was controlled below 0.55% at 50% final concentration, and recovery yield exceeded 99.2%, outperforming conventional distillation in solvent preservation. Additionally, DMI exerted process-stable and scalable properties: vapor flux remained unaffected by DMI concentration (0-33%), and feed temperature and sweep gas flow were identified as key adjustable parameters for process optimization. Membrane and process analysis confirmed consistent dehydration efficiency, minimal solvent cross‑permeation, and predictable scale‑up behavior using empirical modeling. These studies demonstrate that 1,3-dimethyl-2-imidazolidinone possesses significant concentration-enhancing, low-loss and scalable-processing properties in SGMD operations.
The in vitro concentration performance was investigated in a bench‑scale SGMD system with hydrophobic polypropylene hollow-fiber membranes. Aqueous DMI solutions (30-50%) were tested under varied feed temperature (20-67 °C) and sweep air flowrate (20-34 L/min). DMI concentration was monitored by refractometry; vapor flux and loss rates were quantified by humidity measurement and condensate analysis. Empirical models were developed and validated for industrial scale‑up simulation. The results verified that SGMD enables efficient, high‑recovery dehydration of DMI with ultra-low solvent loss, supported by its low vapor pressure and favorable membrane partitioning.

High-Solubility, Low-Overpotential and Cyclability-Enhancing Properties of 1,3-Dimethyl-2-imidazolidinone

Huang, Z. M., Meng, J. T., Zhang, W., Shen, Y., & Huang, Y. H. Science Bulletin, 2022, 67(2), 141‑150.

The physicochemical and electrochemical properties of 1,3-dimethyl-2-imidazolidinone (DMI) were studied using Li-O₂ battery prototypes, electrolyte characterization, and lithium anode stability assays. The main functional characteristic is its high Gutmann donor number (DN = 29) and strong Li⁺ solvation capability, with polar aprotic molecular structure as the core functional feature responsible for its high-solubility, low-overpotential and cyclability-enhancing effects.
DMI exhibited significant high-solubility activity: it achieved Li₂O₂ solubility up to 1.11 mmol L⁻¹ and Li₂CO₃ solubility up to 0.68 mmol L⁻¹, far exceeding DMSO and TEGDME, effectively suppressing cathode passivation. It demonstrated potent low-overpotential effects: the charge overpotential of Li-O₂ batteries was reduced to 0.55 V, nearly half that of conventional electrolytes, with promoted liquid-phase redox shuttling during charging. Additionally, DMI exerted cyclability-enhancing properties: when combined with an artificial SEI-protected Li anode, coulombic efficiency increased from 20% to 98.5%, and cycle life reached 205 rounds at 1000 mAh g⁻¹-five times longer than in DMSO or TEGDME. Electrochemical and structural analyses confirmed suppressed side reactions, accelerated ion transport, and stable electrode-electrolyte interfaces. These studies demonstrate that 1,3-dimethyl-2-imidazolidinone possesses significant high-solubility, low-overpotential and cyclability-enhancing properties for Li-O₂ batteries.
The in vitro electrochemical performance was investigated in 2032 coin-type Li-O₂ cells with carbon nanotube cathodes and Li metal anodes. DMI-based electrolytes were compared with DMSO and TEGDME systems; artificial SEI was formed via fluorine-rich reagent pretreatment. Ionic conductivity, oxidation stability, and solubility were measured; cycle performance, overpotential, and coulombic efficiency were evaluated under 400 mA g⁻¹ current density. The results verified that DMI boosts cathode reaction kinetics and reduces polarization via high peroxide solubility, while stabilized Li anodes enable long‑term reversible cycling.

Aluminum-Electrodepositing, Low-Temperature-Stable and Smooth-Coating Properties of 1,3-Dimethyl-2-imidazolidinone

Endo, A., Miyake, M., & Hirato, T. Electrochimica Acta, 2014, 137, 470-475.

The chemical coordination and electrochemical properties of 1,3-dimethyl-2-imidazolidinone (DMI) were studied using DMI/AlCl₃ bath systems and aluminum electrodeposition assays. The key functional characteristic is its strong molecular coordination with AlCl₃ and wide liquid-phase temperature range, with polar aprotic cyclic structure as the core functional feature responsible for its aluminum-electrodepositing, low-temperature-stable and smooth-coating effects.
DMI exhibited significant aluminum-electrodepositing activity: aluminum metal was successfully deposited from DMI/AlCl₃ baths when AlCl₃ concentration exceeded 50 mol%, driven by electroactive Al₂Cl₇⁻ ions confirmed via IR spectroscopy. It demonstrated potent low-temperature-stable effects: DMI/AlCl₃ baths with 59-64 mol% AlCl₃ remained clear liquid without precipitation at 25 °C, enabling room-temperature aluminum electrodeposition. Additionally, DMI exerted smooth-coating properties: with 0.2 mol% 1,10-phenanthroline as an additive, uniform and compact aluminum films with grain size ~1 μm were obtained at 40 °C, with high current efficiency of approximately 85%. Electrochemical and morphological analyses confirmed pure metallic aluminum deposition, controllable grain size, and low working temperatures compared to conventional organic baths. These studies demonstrate that 1,3-dimethyl-2-imidazolidinone possesses significant aluminum-electrodepositing, low-temperature-stable and smooth-coating properties in non-aqueous electroplating systems.
The in vitro electrodeposition performance was investigated in DMI/AlCl₃ baths with varying AlCl₃ contents (50-64 mol%). Cyclic voltammetry was used to identify electroactive species; potentiostatic and galvanostatic deposition were conducted on copper substrates at 40 °C and 80 °C. IR spectroscopy characterized Al₂Cl₇⁻ formation; SEM and XRD evaluated coating morphology and purity; ICP-AES measured current efficiency. The results verified that DMI forms stable, low-volatility baths supporting aluminum electrodeposition via Al₂Cl₇⁻ reduction at near-ambient temperatures.

Custom Q&A

What is the chemical formula of 1,3-Dimethyl-2-imidazolidinone?

The chemical formula of 1,3-Dimethyl-2-imidazolidinone is C5H10N2O.

What are the synonyms for 1,3-Dimethyl-2-imidazolidinone?

Some synonyms for 1,3-Dimethyl-2-imidazolidinone include Dimethyl imidazolidinone, N,N'-Dimethylimidazolidinone, and Rhonite 1.

What are the hazards associated with 1,3-Dimethyl-2-imidazolidinone?

1,3-Dimethyl-2-imidazolidinone is corrosive, acutely toxic, irritating, and poses health hazards.

What is the molecular structure of 1,3-Dimethyl-2-imidazolidinone?

The molecular structure of 1,3-Dimethyl-2-imidazolidinone is a 2-dimensional and 3-dimensional representation.

What is the IUPAC name of 1,3-Dimethyl-2-imidazolidinone?

The IUPAC name of 1,3-Dimethyl-2-imidazolidinone is 1,3-dimethylimidazolidin-2-one.

What is the InChI of 1,3-Dimethyl-2-imidazolidinone?

The InChI of 1,3-Dimethyl-2-imidazolidinone is InChI=1S/C5H10N2O/c1-6-3-4-7(2)5(6)8/h3-4H2,1-2H3.

What is the InChIKey of 1,3-Dimethyl-2-imidazolidinone?

The InChIKey of 1,3-Dimethyl-2-imidazolidinone is CYSGHNMQYZDMIA-UHFFFAOYSA-N.

What is the canonical SMILES of 1,3-Dimethyl-2-imidazolidinone?

The canonical SMILES of 1,3-Dimethyl-2-imidazolidinone is CN1CCN(C1=O)C.

What is the CAS number of 1,3-Dimethyl-2-imidazolidinone?

The CAS number of 1,3-Dimethyl-2-imidazolidinone is 80-73-9.

What is the European Community (EC) number of 1,3-Dimethyl-2-imidazolidinone?

The European Community (EC) number of 1,3-Dimethyl-2-imidazolidinone is 201-304-8.

Synthetic Use

Upstream Synthesis Route 1

• 201230-82-2
• 110-70-3

• 80-73-9

Reference: [1] Synthesis, 2010, # 24, p. 4251 - 4255
[2] Organic Letters, 1999, vol. 1, # 7, p. 961 - 964

Upstream Synthesis Route 2

• 135-02-4

• 80-73-9

Reference: [1] Journal of the American Chemical Society, 2001, vol. 123, # 31, p. 7705 - 7706

Upstream Synthesis Route 3

• 136-84-5

• 80-73-9

Reference: [1] Patent: US4864026, 1989, A,

Downstream Synthesis Route 1

• 80-73-9
• 79-37-8

• 37091-73-9

Reference: [1]Synthesis,1982,p. 464 - 465

Downstream Synthesis Route 2

• 80-73-9

• 37091-73-9

Reference: [1]Patent: CN105367478,2016,A .Location in patent: Paragraph 0021; 0027; 0028

* For details of the synthesis route, please refer to the original source to ensure accuracy.