5-(4-Bromophenyl)pyrrolidin-2-one: Properties & Lab Use

5-(4-Bromophenyl)pyrrolidin-2-one is a brominated gamma-lactam building block widely employed in medicinal chemistry and heterocyclic synthesis as a versatile intermediate for drug discovery and materials research.

IUPAC Name

5-(4-Bromophenyl)pyrrolidin-2-one

SKU / Catalog Number

B191993

Molecular Formula

C10H10BrNO

Molecular Weight

240.10 g/mol

Compound Class

Gamma-lactam (pyrrolidin-2-one) with aryl bromide substituent

Key Functional Groups

Lactam carbonyl, secondary amine (NH), aryl bromide

Primary Use

Synthetic building block in medicinal and heterocyclic chemistry

What Is 5-(4-Bromophenyl)pyrrolidin-2-one?

5-(4-Bromophenyl)pyrrolidin-2-one (CAS catalog SKU B191993) is a five-membered cyclic amide, classified as a gamma-lactam, bearing a para-bromophenyl substituent at the 5-position of the ring. The molecule combines three synthetically valuable features: (1) a lactam carbonyl amenable to N-alkylation, reduction, or condensation; (2) a secondary NH available for functionalization; and (3) an aryl bromide that serves as a handle for palladium-catalyzed cross-coupling reactions such as Suzuki, Negishi, Heck, and Buchwald–Hartwig couplings.

The stereocenter at C-5 means the compound may be encountered as a racemate or resolved enantiomers depending on the synthetic route. Researchers should confirm the stereochemical specification of the Aladdin lot before use in asymmetric synthesis.

Physicochemical Properties and Specification

The empirical molecular formula is C₁₀H₁₀BrNO with a molecular weight of approximately 240.10 g/mol. The aryl bromide contributes significantly to the molecular weight and provides a characteristic isotope pattern (1:1 ratio for ⁷⁹Br/⁸¹Br) readily confirmed by mass spectrometry. Infrared spectroscopy typically shows a strong lactam C=O stretch near 1680 cm^-1 and a broad N–H stretch around 3200–3300 cm^-1.

Purity specifications for research-grade material from Aladdin Scientific are stated on the product certificate of analysis (CoA). Customers are encouraged to request the CoA at the time of purchase to confirm identity, purity, and residual solvent content. Typical analytical methods include HPLC, NMR (¹H and ¹³C), and melting point determination.

Note: Precise melting point, logP, and solubility values should be verified against the supplied CoA or authoritative chemical databases, as batch-level variations may occur.

Research Applications and Synthetic Utility

5-(4-Bromophenyl)pyrrolidin-2-one is primarily valued as a bifunctional building block in drug discovery programs. The gamma-lactam scaffold is present in a number of biologically active compounds and approved pharmaceuticals, making substituted pyrrolidin-2-ones attractive targets for structure–activity relationship (SAR) studies.

• Cross-coupling chemistry: The aryl bromide at C-4 of the pendant phenyl ring undergoes efficient Suzuki–Miyaura, Negishi, and Heck reactions under standard palladium catalysis, allowing introduction of diverse aryl, vinyl, and alkyl groups.
• N-Functionalization: The lactam NH can be alkylated or acylated to generate N-substituted pyrrolidinones for broader SAR exploration.
• Ring elaboration: Reduction of the carbonyl or ring-opening strategies provide access to pyrrolidine or open-chain amino acid derivatives.
• Chiral synthesis: Enantioselective routes to this scaffold are documented using asymmetric hydrogenation or chiral auxiliary approaches, providing optically enriched intermediates.

These attributes make the compound useful in CNS drug discovery, fragment-based screening libraries, and agrochemical research, although specific biological data should be verified in primary literature.

Handling, Storage, and Safety

As with all laboratory reagents, appropriate personal protective equipment (PPE) including lab coat, nitrile gloves, and safety glasses should be worn when handling 5-(4-Bromophenyl)pyrrolidin-2-one. Work should be conducted in a well-ventilated area or fume hood.

Storage: The compound should be stored in a tightly sealed container, protected from moisture and light, at the temperature specified on the Aladdin product label and CoA (typically room temperature or 2–8 °C, to be confirmed per lot). Organobromide compounds can be sensitive to prolonged exposure to heat and light.

Stability: When stored under recommended conditions, the compound is expected to be stable for the shelf life indicated on the packaging. Re-verification of purity by HPLC or NMR is recommended before use in critical applications if the material has been stored for an extended period.

Disposal: Dispose of waste in accordance with local, regional, and national regulations. Consult the Safety Data Sheet (SDS) provided by Aladdin Scientific for full hazard classification, first-aid measures, and disposal guidance.

Specific GHS hazard classifications for this compound should be confirmed from the Aladdin SDS prior to use.

Ordering and Quality Assurance at Aladdin Scientific

5-(4-Bromophenyl)pyrrolidin-2-one is available from Aladdin Scientific under catalog number B191993. Orders can be placed through the Aladdin website, by contacting a regional sales representative, or via institutional procurement portals that list Aladdin as a supplier.

Certificate of Analysis (CoA): A batch-specific CoA is available for every lot. The CoA includes identity confirmation (NMR, MS, or IR as applicable), purity (HPLC), and physical data. Customers can request the CoA at the time of order or download it from the product page using the lot number.

Quality standards: Aladdin Scientific produces research-grade reagents subject to internal quality control procedures. For applications requiring higher purity (e.g., >99%), customers should contact Aladdin customer service to discuss available grades or custom purification options.

Returns and queries: For product quality concerns, incorrect shipments, or other issues, please refer to Aladdin's returns and refunds policy or contact customer support directly.

Frequently asked questions

What is the molecular formula and molecular weight of 5-(4-Bromophenyl)pyrrolidin-2-one?

The molecular formula is C10H10BrNO and the molecular weight is approximately 240.10 g/mol. The presence of bromine produces a characteristic 1:1 isotope doublet in mass spectra, which is useful for confirming compound identity.

How should 5-(4-Bromophenyl)pyrrolidin-2-one be stored to maintain stability?

The compound should be stored in a tightly sealed container, away from moisture, heat, and direct light, at the temperature recommended on the Aladdin product label and Certificate of Analysis. If the material has been stored for an extended period, purity should be re-verified by HPLC or NMR before use in sensitive applications.

What cross-coupling reactions can be performed using the aryl bromide of this compound?

The aryl bromide substituent on the para-position of the phenyl ring is well-suited for palladium-catalyzed cross-coupling reactions, including Suzuki–Miyaura (with arylboronic acids), Negishi (with organozinc reagents), Heck (with alkenes), and Buchwald–Hartwig amination reactions. These transformations enable efficient diversification of the scaffold for SAR studies.

Is 5-(4-Bromophenyl)pyrrolidin-2-one available as a single enantiomer?

The compound contains a stereocenter at C-5 and may be supplied as a racemate. Researchers requiring a specific enantiomer should contact Aladdin Scientific customer service to inquire about the stereochemical specification of available lots or the feasibility of custom enantioselective synthesis.

How can I obtain a Certificate of Analysis (CoA) for Aladdin catalog number B191993?

A batch-specific CoA for B191993 can be requested at the time of ordering through Aladdin Scientific's website or by contacting customer support directly. You can also download the CoA from the product detail page on the Aladdin website by entering your lot number.

What solvents are typically used to dissolve 5-(4-Bromophenyl)pyrrolidin-2-one?

Gamma-lactam compounds of this class are generally soluble in polar aprotic solvents such as DMSO, DMF, and acetonitrile, and in chlorinated solvents such as DCM. Exact solubility data should be verified experimentally or from the CoA, as specific solubility values for this compound are not stated in the current source material.

References

1. Aladdin Scientific Product Page: 5-(4-Bromophenyl)pyrrolidin-2-one, SKU B191993. Aladdin Scientific Corp.
2. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley-Interscience. (General reference for lactam chemistry and cross-coupling reactions.)
3. Miyaura, N.; Suzuki, A. Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds. Chemical Reviews, 1995, 95(7), 2457–2483. doi:10.1021/cr00039a007

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