Chemical Structure and Key Properties

1-(4-(Benzyloxy)phenyl)-2-bromoethanone (SKU B193369, molecular formula C₁₅H₁₃BrO₂, MW ≈ 305.17 g/mol) features two distinct functional motifs: an alpha-bromoketone (phenacyl bromide) unit and a benzyl ether-protected para-hydroxyphenyl group. The alpha-bromoketone moiety confers high electrophilicity at the methylene carbon, making it an excellent substrate for S_N2 reactions with a wide range of nucleophiles including amines, thioamides, thioureas, and carboxylates. The para-benzyloxy group serves as a protecting group for a phenolic hydroxyl, which can be selectively removed by catalytic hydrogenolysis (e.g., Pd/C, H₂) to unmask the free phenol at a later synthetic stage. This orthogonal protecting-group strategy adds significant synthetic utility to the molecule in multi-step sequences.

The compound typically appears as a white to off-white crystalline solid. Its relatively high molecular weight and the presence of the aromatic bromide-adjacent carbonyl make it amenable to characterization by ¹H NMR (distinct singlet for –CH₂Br near δ 4.4 ppm and benzyl –OCH₂– near δ 5.1 ppm), ¹³C NMR, and mass spectrometry. Researchers should verify all spectral and physical data against the certificate of analysis (CoA) supplied with each batch.

Synthetic Applications in Pharmaceutical and Heterocyclic Chemistry

Alpha-bromoketones are among the most broadly used electrophilic building blocks in heterocyclic synthesis. 1-(4-(Benzyloxy)phenyl)-2-bromoethanone participates in cyclization reactions to construct pharmacologically relevant ring systems, including:

• Oxazoles and Oxazolines – condensation with amides or nitriles under appropriate conditions.
• Thiazoles – reaction with thioamides or thioureas (Hantzsch-type thiazole synthesis) to yield 2-substituted or 2-aminothiazoles bearing the 4-(benzyloxy)phenyl pharmacophore.
• Imidazoles – reaction with formamide or amidines.
• 1,3-Dioxolanes – used as a masked ketone precursor after ketal formation.

The 4-(benzyloxy)phenyl substituent is a privileged scaffold in medicinal chemistry because it mimics the 4-hydroxyphenyl motif found in numerous bioactive natural products and drug candidates, while remaining compatible with a broad range of reaction conditions. After the desired ring system is assembled, the benzyl protecting group can be cleanly removed to reveal the 4-hydroxyphenyl group, enabling further functionalization or final deprotection for biological evaluation.

These attributes make B193369 particularly valuable in library synthesis and structure–activity relationship (SAR) studies targeting kinase inhibitors, antimicrobial agents, and anti-inflammatory scaffolds, among others. Specific yields and conditions should be optimized by the researcher and confirmed against primary literature.

Handling, Storage, and Safety Considerations

As an alpha-bromoketone, 1-(4-(Benzyloxy)phenyl)-2-bromoethanone is a potent alkylating agent and should be handled with appropriate precautions. General guidelines for this class of compound include:

• Personal Protective Equipment (PPE): Wear nitrile gloves, safety glasses or goggles, and a lab coat. Work in a well-ventilated fume hood to minimize inhalation of dust or vapors.
• Skin and Eye Contact: Alpha-bromoketones are known lachrymators and vesicants. Avoid any skin or eye contact. In case of exposure, flush immediately with copious water and seek medical attention.
• Storage: Store in a cool, dry, dark environment, ideally at 2–8 °C or as specified on the product label and SDS. Keep tightly sealed and away from moisture, heat sources, and nucleophilic reagents (amines, thiols) to prevent premature decomposition or reaction.
• Waste Disposal: Dispose of residues and contaminated materials in accordance with local regulations for halogenated organic waste.

Always consult the Safety Data Sheet (SDS) for B193369 before use. The SDS provides authoritative, batch-specific information on hazard classification, first-aid measures, spill response, and regulatory compliance. The information provided here is general guidance only and does not substitute for the SDS.

Ordering and Specifications

Aladdin Scientific offers 1-(4-(Benzyloxy)phenyl)-2-bromoethanone under SKU B193369. When placing an order or requesting a quotation, researchers and procurement teams should confirm the following with Aladdin Scientific directly:

• Available pack sizes – Contact Aladdin Scientific for current stock quantities and custom-pack options.
• Purity grade – Confirm purity specification (e.g., ≥97% or as stated on CoA) relevant to your application.
• Certificate of Analysis (CoA) – Request a batch-specific CoA to verify identity (NMR, HPLC or GC), purity, and appearance prior to use.
• Regulatory documentation – SDS and export/import compliance documents are available upon request.
• Lead time and shipping – Alpha-bromoketones may require specific packaging conditions during shipment. Confirm cold-chain or desiccant requirements with customer service.

For technical inquiries regarding suitability for specific synthetic routes, contact Aladdin Scientific's technical support team. Bulk pricing and custom synthesis inquiries are also welcome.