Ethyl (4-Bromo-2-Fluorobenzoyl)acetate: Key Facts & FAQs

Ethyl (4-bromo-2-fluorobenzoyl)acetate is a halogenated aromatic β-ketoester building block widely used as a synthetic intermediate in medicinal chemistry and the preparation of fluorinated and brominated heterocyclic scaffolds.

CAS Number

Not specified in source material; verify against certificate of analysis

Molecular Formula

C11H10BrFO3

Molecular Weight

Approximately 289.10 g/mol (calculated from molecular formula; verify with CoA)

Functional Class

β-Ketoester (aromatic); halogenated synthetic building block

Key Substituents

4-Bromo and 2-fluoro substituents on the benzoyl ring; ethyl ester group

Aladdin SKU

E469989

Reference Standard

Sigma-Aldrich No. 695769 (cross-reference)

Chemical Identity and Structure

Ethyl (4-bromo-2-fluorobenzoyl)acetate belongs to the class of aromatic β-ketoesters. Its structure consists of a benzoyl group bearing a bromine atom at the para position (C-4) and a fluorine atom at the ortho position (C-2), linked to an ethyl acetate moiety through a ketone carbonyl. The molecular formula is C₁₁H₁₀BrFO₃ with a calculated molecular weight of approximately 289.10 g/mol. The compound exists predominantly in the enol tautomeric form in solution, as is typical for β-ketoesters, and this tautomerism is relevant to its reactivity in condensation and cyclocondensation reactions.

The simultaneous presence of both a C–Br bond and a C–F bond on the aromatic ring provides orthogonal handles for further functionalization: the bromo substituent is amenable to palladium-catalyzed cross-coupling reactions (e.g., Suzuki, Negishi, Buchwald–Hartwig), while the fluoro substituent can modulate the electronic properties of the ring and participate in nucleophilic aromatic substitution under appropriate conditions.

Applications in Organic and Medicinal Chemistry

As a difunctionalized β-ketoester, Ethyl (4-bromo-2-fluorobenzoyl)acetate serves as a versatile intermediate for the construction of pharmacologically relevant heterocyclic scaffolds. β-Ketoesters are classic building blocks in the synthesis of pyrazoles, pyrimidines, isoxazoles, and dihydropyridines through condensation with hydrazines, amidines, hydroxylamines, and enamine-forming reagents, respectively.

The bromo substituent enables late-stage diversification of assembled scaffolds via transition-metal-catalyzed cross-coupling, making this compound particularly attractive for library synthesis and lead optimization in drug discovery programs. The 2-fluoro group on the benzoyl ring is also of interest because fluorine substitution is widely employed in medicinal chemistry to improve metabolic stability, membrane permeability, and binding affinity of candidate drugs.

Typical use concentrations, reaction conditions, and solvent choices will depend on the specific downstream transformation; researchers should consult primary literature for optimized protocols.

Handling, Storage, and Safety

As with most β-ketoester reagents containing halogenated aromatic groups, Ethyl (4-bromo-2-fluorobenzoyl)acetate should be handled with standard laboratory precautions. Work should be performed in a well-ventilated fume hood. Appropriate personal protective equipment (PPE) including chemical-resistant gloves, safety glasses, and a lab coat should be worn at all times during handling.

For storage, the compound should be kept in a tightly sealed container, away from moisture, heat, and incompatible reagents such as strong bases, strong oxidizers, and strong reducing agents. Refrigerated storage (2–8 °C) under an inert atmosphere (nitrogen or argon) is generally recommended to maximize shelf life and minimize decomposition or hydrolysis of the ester functionality. Always consult the current Safety Data Sheet (SDS) provided with the product for detailed hazard classifications, first-aid measures, and disposal requirements.

Note: Specific GHS hazard classifications and pictograms for this compound should be verified against the product SDS; source material does not enumerate specific hazard statements.

Purity, Specification, and Quality

Aladdin Scientific offers Ethyl (4-bromo-2-fluorobenzoyl)acetate under catalogue number E469989, cross-referenced with Sigma-Aldrich No. 695769. Purity specifications, lot-specific analytical data (including NMR, GC, or HPLC purity), and certificates of analysis (CoA) are available upon request or via the Aladdin website product page.

Researchers engaged in sensitive applications such as pharmaceutical synthesis or quantitative structure–activity relationship (QSAR) studies are advised to request a CoA for each lot to confirm identity (e.g., ¹H NMR, ¹⁹F NMR, or mass spectrometry) and purity before use. If higher purity grades are required, contact Aladdin Scientific technical support to discuss available options.

Ordering and Customer Support

Ethyl (4-bromo-2-fluorobenzoyl)acetate (SKU: E469989) can be ordered directly through the Aladdin Scientific website or by contacting our sales team. Standard pack sizes and pricing are listed on the product page; custom quantities may be available upon inquiry.

For questions regarding availability, lead times, bulk pricing, or technical specifications, please reach out to Aladdin Scientific customer service. Returns, refunds, and shipment concerns are handled according to Aladdin's standard policies—please consult the Help and Customer Service section of the website for full details. Academic and institutional accounts may be eligible for reward points, coupons, or credit arrangements under current promotional programs.

Frequently asked questions

What is Ethyl (4-bromo-2-fluorobenzoyl)acetate used for in synthesis?

It is primarily used as a β-ketoester building block for the synthesis of heterocyclic scaffolds such as pyrazoles, isoxazoles, and pyrimidines via condensation reactions. The aryl bromo group also enables palladium-catalyzed cross-coupling reactions for scaffold diversification, making it valuable in medicinal chemistry and drug discovery.

How should Ethyl (4-bromo-2-fluorobenzoyl)acetate be stored to maintain stability?

The compound should be stored in a tightly sealed container under an inert atmosphere (nitrogen or argon) at 2–8 °C, away from moisture, strong bases, and oxidizing agents. These conditions help prevent hydrolysis of the ester group and degradation of the compound over time. Always refer to the current SDS for authoritative storage guidance.

What is the Aladdin Scientific catalogue number for this compound, and is there a Sigma-Aldrich cross-reference?

Aladdin Scientific lists Ethyl (4-bromo-2-fluorobenzoyl)acetate under SKU E469989. It cross-references with Sigma-Aldrich catalogue number 695769, allowing researchers familiar with either supplier to locate the product easily.

Does the compound exist as a single tautomer, and does this affect its reactivity?

Like most β-ketoesters, Ethyl (4-bromo-2-fluorobenzoyl)acetate exists as a mixture of keto and enol tautomers in solution, with the enol form often predominating. This tautomerism is directly relevant to its reactivity: the enol form facilitates condensation reactions with nucleophiles such as hydrazines and amidines to form heterocyclic products. The exact tautomeric ratio depends on solvent and temperature.

Can I request a Certificate of Analysis (CoA) for my purchased lot?

Yes. Lot-specific Certificates of Analysis for E469989 are available through the Aladdin Scientific website product page or upon request from customer service. The CoA typically includes identity confirmation and purity data, which are important for quality-sensitive applications such as pharmaceutical intermediate synthesis.

References

1. Sigma-Aldrich product reference No. 695769 — Ethyl (4-bromo-2-fluorobenzoyl)acetate (cross-reference cited in source material).
2. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley-Interscience. (General reference for β-ketoester chemistry and tautomerism; specific edition not cited in source material.)
3. Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry. Oxford University Press. (General reference for halogenated aromatic cross-coupling and heterocycle synthesis; specific edition not cited in source material.)

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