1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone
CAS 7226-23-5
CAS · 7226-23-5
Product Overview
1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone丨CAS 7226-23-5 is a cyclic urea derivative, structurally similar to DMPU and DMI (dimethylimidazolidinone). It belongs to the family of polar aprotic solvents, known for their high dielectric constant, thermal stability, and ability to dissolve a wide range of polar and ionic compounds. This compound is especially useful in organic synthesis, electrochemistry, and catalysis.
Product Specifications
| Appearance | Colorless or light yellow liquid |
|---|---|
| Purity | 99% min |
| Water | 0.1% max |
Applications
1. Polar Aprotic Solvent in Organic Synthesis
Serves as a high-boiling solvent that stabilizes anions in SN2 reactions, much like DMPU, DMI, or HMPA.
Commonly used in strong base-mediated reactions, including:
Deprotonations with LDA, n-BuLi
Enolate chemistry
Nucleophilic substitutions
2. Alternative to Hazardous Solvents
Provides a less toxic alternative to hexamethylphosphoramide (HMPA), which is carcinogenic.
Suitable for green chemistry applications due to lower health risks while retaining excellent solvating power.
3. Electrolyte Solvent in Electrochemistry
Can be used as a solvent for electrolytes in battery and capacitor research due to its electrochemical stability window and polarity.
Facilitates ion dissociation, enabling smooth charge transport in non-aqueous electrochemical cells.
4. Peptide and Pharmaceutical Synthesis
Useful in peptide coupling reactions, where it enhances solubility and reactivity of intermediates.
Compatible with many amide bond-forming reagents (e.g., EDC, DIC).
5. Catalytic and Transition Metal Chemistry
Acts as a co-solvent or ligand stabilizer in metal-catalyzed processes due to its coordination ability with metal centers.
Suitable for cross-coupling, oxidations, and organometallic transformations.
Benefits
1. Excellent Solvating Power
High dielectric constant and polarity make it efficient at stabilizing ionic species.
Outperforms many conventional solvents in base-promoted or polar reactions.
2. Thermal and Chemical Stability
High boiling point (~200–220°C range estimated, depending on substitution pattern) allows use in high-temperature reactions.
Chemically inert under a wide variety of conditions.
3. Improved Safety Profile
Compared to HMPA or DMPU, may offer reduced toxicity (subject to confirmation via SDS and toxicology reports).
May qualify for safer solvent selection in industrial or academic research.
4. Versatile Usage
Compatible with:
Strong nucleophiles and electrophiles
Anionic polymerization
Cationic intermediates
Organolithium or Grignard reagents
Conclusion
1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone丨CAS 7226-23-5 is a powerful polar aprotic solvent and chemical intermediate, prized for its high thermal stability, broad solvating range, and use in complex organic reactions. It is an effective, potentially safer alternative to traditional solvents like HMPA and DMPU, playing a key role in modern synthetic organic and electrochemical methodologies.
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