2-(4-Bromophenyl)acetophenone: Properties, Uses & Lab Guide

2-(4-Bromophenyl)acetophenone is a halogenated diaryl ketone building block of broad utility in organic synthesis, serving as a reactive intermediate for the preparation of heterocyclic scaffolds, pharmaceutical precursors, and functionalized arene derivatives.

Chemical Name

2-(4-Bromophenyl)acetophenone

Molecular Formula

C₁₄H₁₁BrO

Molecular Weight

275.14 g/mol

Functional Groups

Aryl bromide, ketone (carbonyl)

Key Reactivity

Electrophilic carbonyl reactions, cross-coupling at C–Br, enolization, cyclization

Storage Conditions

Store in a cool, dry, well-ventilated area away from light and moisture; keep container tightly closed

Supplier SKU

A727516 — Aladdin Scientific

Physicochemical Properties and Structure

2-(4-Bromophenyl)acetophenone is a diaryl ketone in which a phenacyl (benzoylmethyl) group is connected to a para-bromophenyl ring. Its molecular formula is C₁₄H₁₁BrO with a molecular weight of approximately 275.14 g/mol. The molecule features two distinct reactive sites: the electrophilic carbonyl carbon of the ketone and the aryl C–Br bond, making it a bifunctional handle for diverse transformations.

The compound typically appears as a white to off-white crystalline solid at ambient temperature. The carbonyl group activates the adjacent methylene (–CH₂–) toward enolization and nucleophilic addition, while the para-bromine substituent on the second arene ring enables oxidative addition into palladium and other transition-metal catalysts, facilitating cross-coupling chemistry.

Solubility: the compound is generally soluble in common organic solvents such as dichloromethane, tetrahydrofuran, ethyl acetate, and dimethylformamide, and sparingly soluble in water. These solubility characteristics align with its lipophilic diaryl ketone structure.

Applications in Organic and Medicinal Chemistry Synthesis

The dual functionality of 2-(4-Bromophenyl)acetophenone—an activated methylene flanked by a phenyl ketone and an aryl bromide—makes it a versatile building block in multi-step synthesis. Key application areas include:

• Heterocycle synthesis: The active methylene and carbonyl groups participate in condensation reactions with nitrogen and sulfur dinucleophiles to construct chalcone-derived heterocycles such as pyrazoles, isoxazoles, thiazoles, and imidazoles. These scaffolds are central to pharmaceutical lead discovery.
• Transition-metal-catalyzed cross-coupling: The aryl bromide undergoes Suzuki–Miyaura, Heck, Sonogashira, and Buchwald–Hartwig reactions, enabling introduction of diverse aryl, alkenyl, alkynyl, or amino groups onto the molecule, expanding the structural diversity of products derived from a single precursor.
• Chalcone synthesis: Aldol-type condensation of the methylene group with aromatic aldehydes yields chalcones, important pharmacophores with reported anti-inflammatory, antifungal, and anticancer bioactivities.
• Pharmaceutical and agrochemical intermediates: The compound serves as a precursor to a range of biologically active targets, including kinase inhibitors and antimicrobial agents, where the bromophenyl moiety is a common pharmacophoric element.

Its defined molecular architecture and dual reactivity sites allow chemists to modulate both ends of the molecule in a sequential or one-pot fashion, simplifying the synthesis of structurally complex targets.

Safe Handling, Storage, and Waste Disposal

Hazard overview: 2-(4-Bromophenyl)acetophenone should be treated as a potentially irritating organic solid. As with most aryl ketone reagents, it may cause irritation to the skin, eyes, and respiratory tract upon direct contact or inhalation of dust. Consult the current Safety Data Sheet (SDS) supplied by Aladdin Scientific before use.

Personal protective equipment (PPE): Wear appropriate chemical-resistant gloves (e.g., nitrile), safety goggles, and a laboratory coat when handling. Where dust generation is anticipated, use a fume hood or respiratory protection.

Storage: Store in a tightly sealed container in a cool (below 25 °C), dry location away from direct light, heat sources, and incompatible materials such as strong oxidizers and strong bases. Desiccant use is recommended to prevent moisture uptake and potential hydrolysis of the carbonyl functionality.

Waste disposal: Dispose of this compound and contaminated materials in accordance with local, regional, and national regulations governing halogenated organic waste. Do not pour down drains or discharge to the environment. Use designated waste containers and engage a licensed waste disposal contractor.

Spill management: Contain spills with inert absorbent material (e.g., vermiculite or sand), collect mechanically, and transfer to a labeled waste container. Ventilate the area and avoid raising dust.

Laboratory Protocol: Preparation and Handling Best Practices

The following procedural guidelines help ensure reproducible results and reagent integrity when working with 2-(4-Bromophenyl)acetophenone:

1. Pre-use inspection: Inspect the reagent upon receipt. The material should appear as a free-flowing crystalline solid. Discoloration or caking may indicate degradation or moisture exposure; contact Aladdin Scientific if product quality is in question.
2. Weighing: Tare an appropriate vessel on an analytical balance inside a fume hood. Transfer the required quantity quickly to minimize atmospheric exposure. Re-seal the stock container immediately after use.
3. Dissolution: For reaction setup, dissolve the weighed solid in the chosen anhydrous organic solvent (e.g., dry DMF, THF, or DCM). Sonication or gentle warming may aid dissolution. Filter through a syringe filter if particulates are observed.
4. Reaction conditions — cross-coupling example: For Suzuki coupling, combine the aryl bromide substrate with the boronic acid partner (1.2–1.5 equiv), a palladium catalyst (e.g., Pd(PPh₃)₄, 2–5 mol%), base (e.g., K₂CO₃ or Cs₂CO₃, 2–3 equiv), and solvent (e.g., toluene/water or DMF/water) under inert atmosphere. Heat to 80–100 °C and monitor by TLC or HPLC.
5. Reaction conditions — chalcone synthesis example: Dissolve 2-(4-Bromophenyl)acetophenone in ethanol, add the chosen aromatic aldehyde (1.0–1.2 equiv) and a catalytic or stoichiometric base (e.g., NaOH or piperidine). Stir at room temperature or under mild heating; monitor by TLC. Collect the precipitated chalcone product by filtration or extraction.
6. Workup and purification: Standard aqueous workup followed by column chromatography (silica gel, hexane/ethyl acetate gradient) or recrystallization from ethanol or isopropanol typically affords pure products.
7. Analytical characterization: Confirm product identity by ¹H NMR, ¹³C NMR, IR spectroscopy, and high-resolution mass spectrometry (HRMS). The carbonyl stretch near 1680–1700 cm⁻¹ and the characteristic aromatic signals are diagnostic.

Quality, Purity, and Procurement from Aladdin Scientific

Aladdin Scientific supplies 2-(4-Bromophenyl)acetophenone under SKU A727516. Researchers should review the product page for the current certificate of analysis (CoA), which details purity specifications, analytical data (e.g., GC purity), lot-specific information, and physical property data.

Purity considerations: For sensitive synthetic applications—particularly transition-metal-catalyzed cross-coupling reactions—high purity (typically ≥97% or ≥98% GC) is recommended to minimize catalyst poisoning or side reactions from trace impurities. Confirm purity grade before ordering by consulting the product specification sheet.

Quantity and packaging: Available in research-scale quantities. Contact Aladdin Scientific sales or procurement teams for bulk pricing, custom packaging, or availability of specific lots.

Regulatory and documentation: Lot-specific CoA, SDS, and regulatory documents (where applicable) can be requested through Aladdin Scientific's customer service. Ensure all documentation is retained for laboratory records and compliance purposes.

Ordering: Place orders through the Aladdin Scientific website or through your institution's preferred procurement channel. Quote SKU A727516 for accurate fulfillment.

Frequently asked questions

What is 2-(4-Bromophenyl)acetophenone used for in organic synthesis?

It serves as a bifunctional building block exploiting its activated methylene-carbonyl motif and the aryl bromide handle. Common uses include Suzuki–Miyaura and Heck cross-coupling reactions at the C–Br position, condensation with aromatic aldehydes to form chalcones, and cyclization with N/S dinucleophiles to construct heterocyclic scaffolds such as pyrazoles, isoxazoles, and thiazoles relevant to drug discovery.

How should I store 2-(4-Bromophenyl)acetophenone to maintain its stability?

Store the compound in a tightly sealed container in a cool (below 25 °C), dry location protected from light and heat. The use of a desiccant is recommended to prevent moisture ingress, which could promote slow hydrolysis of the ketone or physical caking of the solid. Avoid prolonged exposure to air when weighing.

Which Aladdin Scientific SKU corresponds to 2-(4-Bromophenyl)acetophenone?

2-(4-Bromophenyl)acetophenone is available from Aladdin Scientific under SKU A727516. When placing an order, quoting this SKU ensures accurate product fulfillment. A current certificate of analysis and safety data sheet are available through the product page or customer service.

What purity grade is recommended for cross-coupling reactions using this compound?

For transition-metal-catalyzed cross-coupling reactions such as Suzuki–Miyaura coupling, a purity of ≥97% (GC) or higher is recommended. Trace impurities, especially sulfur- or phosphorus-containing compounds, can deactivate the palladium catalyst and reduce yields. Always confirm purity from the lot-specific CoA before use.

What safety precautions are necessary when handling this compound?

Treat 2-(4-Bromophenyl)acetophenone as a potential irritant. Wear nitrile gloves, safety goggles, and a lab coat. Handle in a well-ventilated fume hood, especially when weighing powder, to avoid dust inhalation. Consult the current SDS from Aladdin Scientific for full hazard classification, first-aid measures, and disposal requirements before beginning work.

References

1. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. 4th ed. Wiley, 1992. General reference for carbonyl chemistry and cross-coupling reactions.
2. Miyaura, N.; Suzuki, A. Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds. Chemical Reviews, 1995, 95(7), 2457–2483. doi:10.1021/cr00039a007
3. Patai, S. (Ed.) The Chemistry of the Carbonyl Group. Wiley-Interscience, 1966. Reference for ketone reactivity and enolization chemistry.
4. Aladdin Scientific. Product Page: 2-(4-Bromophenyl)acetophenone, SKU A727516. Aladdin Scientific Co., Ltd.

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