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

2-(4-Bromophenyl)acetophenone is a halogenated diaryl ketone building block widely employed in organic synthesis as a versatile intermediate for constructing heterocyclic frameworks, pharmaceutical precursors, and functionalized aromatic compounds.

IUPAC Name

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

Molecular Formula

C₁₄H₁₁BrO

Molecular Weight

275.14 g/mol

Functional Groups

Aryl ketone (C=O), aryl bromide (C–Br)

Key Reactivity

Electrophilic carbonyl and nucleofugal bromide enable cross-coupling, cyclization, and α-functionalization reactions

Typical Appearance

Off-white to pale yellow solid

SKU

A727516

Chemical Identity and Physical Properties

2-(4-Bromophenyl)acetophenone (CAS: a review flag applies — see flags) is a diaryl ketone with the molecular formula C₁₄H₁₁BrO and a molecular weight of approximately 275.14 g/mol. The compound features a phenacyl (PhC(O)CH₂–) backbone in which the methylene bears a 4-bromophenyl substituent, making it a bifunctional molecule: the carbonyl group acts as an electrophilic handle while the aryl bromide serves as a site for metal-catalyzed cross-coupling reactions.

Physically, the compound is typically encountered as an off-white to pale yellow crystalline solid. It is sparingly soluble in water but readily dissolves in common organic solvents such as dichloromethane, ethyl acetate, tetrahydrofuran, and acetone. The carbonyl stretch in the IR spectrum appears in the characteristic ketone region (~1680–1700 cm⁻¹), and the aromatic bromide is confirmed by the distinctive isotope pattern in mass spectrometry.

Synthesis Context and Reaction Chemistry

The dual electrophilic–leaving-group character of 2-(4-Bromophenyl)acetophenone makes it an attractive intermediate in multi-step organic synthesis. The α-methylene protons are relatively acidic (flanked by a carbonyl), facilitating base-mediated enolization and subsequent alkylation, halogenation, or condensation reactions. This α-reactivity is routinely exploited for the construction of 1,3-dicarbonyl systems and heterocyclic scaffolds such as pyrazoles, isoxazoles, and chalcone-derived rings.

The aryl bromide moiety on the 4-bromophenyl ring is an ideal partner for palladium-catalyzed reactions including Suzuki–Miyaura coupling, Heck reactions, and Buchwald–Hartwig amination, allowing downstream diversification of the aromatic ring without disturbing the ketone functionality. Researchers working on medicinal chemistry and materials science libraries frequently use such bifunctional ketone-halide building blocks to generate compound arrays in parallel synthesis workflows.

Handling, Storage, and Safety Guidelines

As with all aryl ketones and organobromine compounds, standard laboratory safety practices should be observed when handling 2-(4-Bromophenyl)acetophenone. Work should be conducted in a well-ventilated fume hood. Appropriate personal protective equipment (PPE) including chemical-resistant gloves, safety goggles, and a laboratory coat is mandatory.

The compound should be stored in a tightly sealed container, away from heat sources and incompatible materials such as strong oxidizers and strong bases. A cool, dry environment (typically 2–25 °C) is recommended to maintain long-term stability. Consult the product-specific Safety Data Sheet (SDS) provided by Aladdin Scientific (SKU A727516) for complete hazard classifications, first-aid measures, and disposal instructions in accordance with local regulations.

Research Applications

2-(4-Bromophenyl)acetophenone serves as a key synthetic building block across several research disciplines:

• Medicinal Chemistry: Used as a precursor for the preparation of chalcones, flavanones, and other pharmacophores with reported biological activities including anti-inflammatory, antimicrobial, and antitumor properties.
• Heterocyclic Synthesis: Condensation with hydrazines, hydroxylamines, or ammonium acetate enables access to pyrazoles, isoxazoles, and pyrimidines, respectively, which are privileged scaffolds in drug discovery.
• Cross-Coupling Libraries: The intact aryl bromide allows Suzuki or Heck reactions to install diverse aryl, vinyl, or alkyl groups, dramatically expanding chemical space from a single starting material.
• Materials Science: Aryl ketones with extended conjugation are investigated as intermediates for organic electronic materials and photoactive compounds.

Aladdin Scientific supplies this compound (SKU A727516) to support researchers requiring reliable, consistently pure reagents for demanding synthetic programs.

Frequently asked questions

What is the molecular formula and weight of 2-(4-Bromophenyl)acetophenone?

2-(4-Bromophenyl)acetophenone has the molecular formula C₁₄H₁₁BrO and a molecular weight of approximately 275.14 g/mol. It contains one carbonyl group and one aryl bromide functional group.

What solvents are recommended for dissolving 2-(4-Bromophenyl)acetophenone?

The compound dissolves readily in common organic solvents including dichloromethane, ethyl acetate, tetrahydrofuran, and acetone. It is sparingly soluble in water and should not be dissolved in strongly basic or strongly oxidizing solvent systems without prior compatibility assessment.

How should 2-(4-Bromophenyl)acetophenone (A727516) be stored?

Store the compound in a tightly sealed container in a cool, dry place (2–25 °C), away from heat, direct sunlight, strong oxidizers, and strong bases. Always consult the Aladdin Scientific SDS for the most current storage and handling recommendations.

Can the aryl bromide in 2-(4-Bromophenyl)acetophenone be used in palladium-catalyzed cross-coupling?

Yes. The 4-bromophenyl group is a well-established electrophilic partner for palladium-catalyzed reactions such as Suzuki–Miyaura, Heck, and Buchwald–Hartwig couplings. These reactions allow researchers to diversify the aromatic ring independently of the ketone functionality.

What heterocyclic compounds can be synthesized from 2-(4-Bromophenyl)acetophenone?

The compound's reactive α-methylene and carbonyl groups enable condensation with hydrazines to form pyrazoles, with hydroxylamines to form isoxazoles, and with ammonium acetate or urea derivatives to form pyrimidines and related N-containing heterocycles. These scaffolds are of high interest in medicinal chemistry and drug discovery.

References

1. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. 4th ed. Wiley-Interscience, 1992. (General reference for ketone and aryl halide reactivity.)
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. Aladdin Scientific. Product page and Safety Data Sheet for 2-(4-Bromophenyl)acetophenone, SKU A727516.

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