1-(5-Bromo-2-methoxyphenyl)ethanone: Properties & Lab Use Guide

1-(5-Bromo-2-methoxyphenyl)ethanone is a halogenated aromatic ketone widely employed as a versatile intermediate in organic synthesis and medicinal chemistry research.

IUPAC Name

1-(5-Bromo-2-methoxyphenyl)ethanone

Aladdin SKU

B587602

Molecular Formula

C₉H₉BrO₂

Molecular Weight

229.07 g/mol

CAS Number

7697-26-9

Functional Groups

Ketone (acetyl), aryl bromide, methoxy ether

Typical Appearance

Off-white to pale yellow crystalline solid

Storage Condition

Store at room temperature in a cool, dry place away from light

Chemical Identity and Physical Properties

1-(5-Bromo-2-methoxyphenyl)ethanone (CAS 7697-26-9, Aladdin SKU B587602) is an acetophenone derivative bearing two key substituents on the phenyl ring: a bromine atom at the 5-position and a methoxy group at the 2-position (ortho to the carbonyl). Its molecular formula is C₉H₉BrO₂ with a molecular weight of approximately 229.07 g/mol.

The compound typically presents as an off-white to pale yellow crystalline solid at ambient temperature. The electron-donating methoxy group and the electron-withdrawing bromine and acetyl groups create a well-defined electronic environment that governs its reactivity in downstream transformations. The ortho-methoxy substitution pattern relative to the carbonyl can influence conformation and intramolecular interactions, which may be exploited in directed metalation strategies.

Note: Specific melting point, boiling point, and solubility data should be verified against the certificate of analysis (CoA) supplied with each batch (SKU B587602). Researchers should consult the product-specific CoA for confirmed physicochemical constants.

Synthetic Applications and Reactivity

The three functional handles present in 1-(5-Bromo-2-methoxyphenyl)ethanone make it a strategically valuable building block in synthetic organic chemistry:

• Aryl Bromide (C–Br bond): The aryl bromide at C-5 is highly amenable to palladium-catalyzed cross-coupling reactions, including Suzuki–Miyaura, Negishi, Kumada, Heck, and Buchwald–Hartwig couplings. These transformations allow rapid diversification of the aromatic core for the construction of biaryl frameworks commonly found in pharmaceuticals and agrochemicals.
• Ketone (Acetyl group): The carbonyl can participate in nucleophilic addition, condensation reactions (e.g., aldol, Knoevenagel), reductive amination, and Wittig-type olefination. The methyl ketone is also a useful handle for enolization chemistry.
• Methoxy Group: Under specific conditions, the aryl methoxy group can be demethylated (e.g., with BBr₃ or AlCl₃) to reveal a phenol, opening routes to further functionalization or O-alkylation.

This combination of handles renders the compound particularly useful in the preparation of pharmaceutical intermediates, agrochemical precursors, and novel materials. Researchers working on structure–activity relationship (SAR) studies benefit from the modularity this scaffold provides.

Handling, Safety, and Storage Guidelines

As with all laboratory reagents, standard precautions should be observed when handling 1-(5-Bromo-2-methoxyphenyl)ethanone. Although this compound is not classified among the most hazardous reagents, good laboratory practice (GLP) requires the following measures:

• Personal Protective Equipment (PPE): Wear appropriate chemical-resistant gloves (e.g., nitrile), safety goggles, and a laboratory coat. Work in a well-ventilated fume hood to minimize dust or vapor inhalation.
• Skin and Eye Contact: Avoid direct contact. In case of skin contact, wash thoroughly with soap and water. For eye contact, flush immediately with large amounts of water and seek medical attention.
• Storage: Store at room temperature in a cool, dry location away from direct light and moisture. Keep the container tightly sealed when not in use to prevent moisture uptake and degradation.
• Disposal: Dispose of waste material in accordance with local, regional, and national regulations for halogenated organic compounds.

Important: Always consult the Safety Data Sheet (SDS) specific to SKU B587602 prior to use. The SDS contains authoritative hazard classifications, first-aid measures, and regulatory compliance information.

Quality, Purity, and Procurement Considerations

For research and development applications, reagent purity is critical to reproducibility. Aladdin Scientific supplies 1-(5-Bromo-2-methoxyphenyl)ethanone under SKU B587602. Researchers and procurement personnel should consider the following when ordering:

• Purity Specification: Confirm the purity grade (e.g., ≥97% or ≥98% by GC or HPLC) directly from the product listing or CoA available on the Aladdin Scientific website. Specific lot purity values are reported on the CoA accompanying each shipment.
• Analytical Characterization: Each batch is typically characterized by techniques such as GC, HPLC, NMR, and/or elemental analysis. Contact Aladdin Scientific technical support for CoA documentation specific to your lot number.
• Pack Sizes and Lead Times: Available pack sizes and current stock status should be confirmed at the time of ordering via the Aladdin Scientific catalog or sales representative.
• Regulatory Documentation: For GMP-adjacent or regulated research environments, inquire with Aladdin Scientific about available documentation such as SDS, CoA, and REACH compliance statements.

Procurement teams are encouraged to reference SKU B587602 in purchase orders to ensure accurate fulfillment and traceability.

Frequently asked questions

What is the CAS number for 1-(5-Bromo-2-methoxyphenyl)ethanone?

The CAS registry number for 1-(5-Bromo-2-methoxyphenyl)ethanone is 7697-26-9. It is available from Aladdin Scientific under SKU B587602. Always verify the CAS number against the product CoA upon receipt.

Which cross-coupling reactions are compatible with 1-(5-Bromo-2-methoxyphenyl)ethanone?

The aryl bromide functionality at C-5 makes this compound compatible with a range of palladium-catalyzed cross-coupling reactions, including Suzuki–Miyaura (with boronic acids/esters), Negishi (with organozinc reagents), Heck (with alkenes), and Buchwald–Hartwig amination. Reaction conditions should be optimized for the specific coupling partner and catalyst system used.

How should 1-(5-Bromo-2-methoxyphenyl)ethanone be stored to maintain stability?

This compound should be stored at room temperature in a cool, dry environment away from direct light and sources of moisture. Keep the container tightly closed between uses. For long-term storage recommendations specific to your lot, consult the CoA or SDS provided with SKU B587602.

What is the molecular weight of 1-(5-Bromo-2-methoxyphenyl)ethanone?

The molecular weight of 1-(5-Bromo-2-methoxyphenyl)ethanone (C₉H₉BrO₂) is approximately 229.07 g/mol. This value is calculated from the molecular formula and is consistent with standard chemical databases.

Can the methoxy group in 1-(5-Bromo-2-methoxyphenyl)ethanone be removed to give the corresponding phenol?

Yes, the aryl methoxy group can be cleaved under demethylation conditions commonly used in organic synthesis, such as treatment with boron tribromide (BBr₃) in dichloromethane at low temperature, or with aluminum chloride (AlCl₃). The resulting phenol can then be further functionalized as required. Reaction conditions must be carefully controlled to avoid undesired side reactions with the ketone or aryl bromide.

References

1. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 4th ed.; Wiley-Interscience: New York, 1992. (General reference for aryl ketone reactivity and cross-coupling context.)
2. Miyaura, N.; Suzuki, A. Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds. Chem. Rev. 1995, 95, 2457–2483. doi:10.1021/cr00039a007
3. Aladdin Scientific. Product page and Certificate of Analysis for 1-(5-Bromo-2-methoxyphenyl)ethanone, SKU B587602. Aladdin Scientific Corp.

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