1-(4-Bromophenyl)imidazolidin-2-one: Properties & Lab Guide

1-(4-Bromophenyl)imidazolidin-2-one is a brominated cyclic urea heterocycle widely employed as a versatile building block in medicinal chemistry, organic synthesis, and drug discovery research.

Product Name

1-(4-Bromophenyl)imidazolidin-2-one

SKU

I729329

Molecular Formula

C9H9BrN2O

Molecular Weight

241.08 g/mol

Core Scaffold

Imidazolidin-2-one (cyclic urea) with a 4-bromophenyl substituent at N-1

Key Functional Handle

Aryl bromide, suitable for cross-coupling reactions (e.g., Suzuki, Buchwald-Hartwig)

Supplier

Aladdin Scientific

Chemical Identity and Structure

1-(4-Bromophenyl)imidazolidin-2-one (SKU I729329) consists of a five-membered cyclic urea ring—the imidazolidin-2-one core—bearing a para-bromophenyl group at the N-1 nitrogen. The imidazolidin-2-one scaffold is an important pharmacophore found in numerous bioactive molecules and approved drugs. The carbonyl group at the 2-position confers hydrogen-bond donor and acceptor capability, while the aryl bromide at the para position provides a synthetically versatile handle for further functionalization. The compound is a solid at ambient temperature and should be stored in a cool, dry location away from light to maintain stability.

Research Applications

1-(4-Bromophenyl)imidazolidin-2-one serves as a key intermediate in medicinal chemistry and drug discovery. Its primary utility derives from two complementary features: the cyclic urea pharmacophore and the reactive aryl bromide.

• Cross-coupling chemistry: The aryl bromide undergoes Suzuki–Miyaura, Negishi, Buchwald–Hartwig, and related palladium-catalyzed coupling reactions, enabling rapid diversification of the imidazolidinone scaffold.
• Pharmacophore incorporation: The imidazolidin-2-one ring is a bioisostere for hydantoin and related scaffolds, and is incorporated into libraries targeting enzyme inhibition and receptor modulation.
• Fragment-based drug discovery: As a fragment-sized molecule, it is suitable for fragment screening campaigns against diverse biological targets.
• Material science: N-aryl cyclic ureas have been explored as monomers or modifiers in polymer and materials research.

Researchers should verify suitability for specific biological assays, as activity data depend on the target and assay conditions.

Handling, Safety, and Storage Guidelines

When working with 1-(4-Bromophenyl)imidazolidin-2-one, standard laboratory safety practices apply. The compound contains an aryl bromide, and general precautions for organic reagents should be observed:

• Personal protective equipment (PPE): Wear appropriate laboratory coat, chemical-resistant gloves, and safety goggles when handling the compound.
• Ventilation: Handle in a well-ventilated area or fume hood to minimize inhalation exposure.
• Storage: Store tightly sealed in a cool (2–25 °C recommended), dry environment protected from light and moisture. Keep away from incompatible materials such as strong oxidizers and bases.
• Disposal: Dispose of in accordance with local and institutional regulations for organic chemical waste.

Consult the Safety Data Sheet (SDS) supplied by Aladdin Scientific for complete hazard information before use. Specific GHS classifications should be verified from the current SDS.

Recommended Handling Protocols for Common Reactions

The following general protocols outline best practices for utilizing 1-(4-Bromophenyl)imidazolidin-2-one in typical synthetic transformations:

1. Suzuki–Miyaura Cross-Coupling: Combine the aryl bromide with an appropriate boronic acid or ester in the presence of a palladium catalyst (e.g., Pd(PPh₃)₄ or Pd(dppf)Cl₂), a base (e.g., K₂CO₃ or Cs₂CO₃), and a suitable solvent system (e.g., DMF/water or dioxane/water) under inert atmosphere at elevated temperature (80–100 °C). Monitor by TLC or HPLC.
2. Buchwald–Hartwig Amination: React the aryl bromide with a primary or secondary amine using a palladium source, a bidentate phosphine ligand, and a strong base (e.g., NaOtBu) in toluene or dioxane under nitrogen atmosphere.
3. Lithiation/Metal-Halogen Exchange: At low temperature (−78 °C), treat with n-BuLi in dry THF under inert atmosphere to generate the aryllithium species for further electrophilic trapping; exercise caution due to cryogenic and pyrophoric reagent requirements.

All reaction conditions should be optimized for specific substrates and scales. Consult primary literature for detailed procedures and yield data.

Frequently asked questions

What is 1-(4-Bromophenyl)imidazolidin-2-one used for in research?

It is primarily used as a synthetic building block in medicinal chemistry and drug discovery. The aryl bromide enables cross-coupling reactions such as Suzuki–Miyaura and Buchwald–Hartwig couplings, while the imidazolidinone ring serves as a pharmacophore or bioisostere in bioactive compound libraries.

How should 1-(4-Bromophenyl)imidazolidin-2-one be stored to maintain its integrity?

The compound should be stored in a tightly sealed container in a cool (2–25 °C), dry, and dark environment, away from moisture, strong oxidizers, and bases. Proper sealing prevents moisture uptake and degradation over time.

Is 1-(4-Bromophenyl)imidazolidin-2-one suitable for palladium-catalyzed cross-coupling reactions?

Yes. The para-aryl bromide is an excellent electrophilic partner for palladium-catalyzed reactions including Suzuki–Miyaura, Negishi, and Buchwald–Hartwig couplings. Reaction conditions should be optimized based on the specific coupling partner and scale.

Where can I find the Safety Data Sheet (SDS) for this compound?

The SDS for 1-(4-Bromophenyl)imidazolidin-2-one (SKU I729329) is available on the Aladdin Scientific website product page. Always consult the current SDS before handling any chemical reagent to ensure compliance with safety regulations.

What is the molecular formula and molecular weight of 1-(4-Bromophenyl)imidazolidin-2-one?

The molecular formula is C9H9BrN2O and the molecular weight is approximately 241.08 g/mol. Researchers should verify these values against the certificate of analysis (CoA) supplied with the product.

References

1. Larock, R. C. Comprehensive Organic Transformations: A Guide to Functional Group Preparations. Wiley-VCH, 1999. (General reference for cross-coupling reactions of aryl halides.)
2. Negishi, E. (Ed.) Handbook of Organopalladium Chemistry for Organic Synthesis. Wiley-Interscience, 2002. (Reference for palladium-catalyzed coupling methodologies.)
3. Aladdin Scientific. Product page for 1-(4-Bromophenyl)imidazolidin-2-one, SKU I729329. (Supplier product and SDS information.)

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.