2-Bromo-1-(4-chloro-2-fluorophenyl)ethanone: Key Facts & FAQs

2-Bromo-1-(4-chloro-2-fluorophenyl)ethanone is a halogenated α-bromoacetophenone building block bearing both chloro and fluoro substituents on the aromatic ring, widely employed as a reactive electrophilic intermediate in the synthesis of pharmaceuticals, agrochemicals, and heterocyclic compounds.

Product Name

2-Bromo-1-(4-chloro-2-fluorophenyl)ethanone

SKU

B590003

Molecular Formula

C8H5BrClFO

Molecular Weight

251.48 g/mol

Functional Class

α-Bromoketone / Electrophilic alkylating agent

Primary Use

Synthetic intermediate for pharmaceuticals and heterocyclic chemistry

Chemical Identity and Structure

2-Bromo-1-(4-chloro-2-fluorophenyl)ethanone (CAS number should be confirmed; SKU B590003) is an α-haloketone in which a bromine atom is located at the alpha carbon of the acetyl group. The aryl ring carries a chlorine substituent at the 4-position and a fluorine substituent at the 2-position, creating a multifunctional halogenated scaffold. The molecular formula is C₈H₅BrClFO with a molecular weight of approximately 251.48 g/mol. The combination of electron-withdrawing halogens on the ring influences the electrophilicity of the carbonyl and the reactivity of the alpha-bromo leaving group, making this compound a versatile electrophile in organic synthesis.

Synthetic Applications and Reactivity

As an α-bromoketone, 2-Bromo-1-(4-chloro-2-fluorophenyl)ethanone participates in a broad range of nucleophilic substitution and condensation reactions. Key applications include:

• Heterocycle synthesis: Reaction with thioamides, guanidines, or amidines produces thiazoles, imidazoles, and related nitrogen–sulfur heterocycles that are important pharmacophores.
• Alkylation of heteroatom nucleophiles: The reactive C–Br bond undergoes efficient S-, N-, and O-alkylation with thiols, amines, and alcohols under mild conditions.
• Pharmaceutical intermediates: The fluorine and chlorine substituents are commonly retained in drug candidates to modulate lipophilicity, metabolic stability, and target binding.
• Cross-coupling precursor: After appropriate functional-group manipulation, the aryl chloride can serve as a handle for palladium-catalyzed cross-coupling reactions.

The dual halogen substitution pattern on the ring makes this building block particularly attractive for medicinal chemistry programs targeting kinases, antimicrobials, and other therapeutic areas.

Handling, Safety, and Storage

α-Bromoketones are potent lachrymators and alkylating agents and must be handled with appropriate precautions:

• Personal protective equipment: Use nitrile gloves, a lab coat, and safety glasses as a minimum. Work in a well-ventilated fume hood to avoid inhalation of vapors.
• Skin and eye contact: Avoid direct contact; in case of skin contact wash thoroughly with soap and water. In case of eye contact, irrigate immediately with copious water and seek medical attention.
• Storage: Store in a tightly sealed container in a cool, dry, well-ventilated area away from moisture, heat sources, and incompatible materials such as strong bases and reducing agents. Refrigerated storage (2–8 °C) is generally recommended for long-term stability.
• Waste disposal: Dispose of in accordance with local, regional, and national regulations for halogenated organic waste.

Always consult the Safety Data Sheet (SDS) provided by Aladdin Scientific before use.

Quality, Purity, and Specifications

Aladdin Scientific supplies 2-Bromo-1-(4-chloro-2-fluorophenyl)ethanone (SKU B590003) as a research-grade reagent. Typical quality attributes include:

• Purity: Verified by HPLC or GC; customers should consult the Certificate of Analysis (CoA) supplied with each lot for the exact purity figure, as specifications may vary by batch.
• Characterization: Identity is confirmed by techniques such as ¹H NMR and/or mass spectrometry.
• Appearance: Typically a solid or low-melting crystalline material; exact physical form should be confirmed on the CoA.
• Lot-specific data: Each shipment is accompanied by a CoA detailing purity, melting point (if applicable), and analytical data. Contact Aladdin Scientific customer service to request CoA documentation for a specific lot.

Ordering and Customer Support

2-Bromo-1-(4-chloro-2-fluorophenyl)ethanone is available from Aladdin Scientific under SKU B590003. To place an order or request additional information:

• Visit the Aladdin Scientific website and search by SKU B590003 or by product name.
• Contact our sales team for bulk pricing, custom pack sizes, or expedited shipping options.
• For technical questions regarding purity specifications, CoA requests, or application support, reach out to our technical support team.
• Returns and replacements are handled according to Aladdin Scientific's standard returns and refund policy; please contact customer service within the applicable window after receipt of goods.

Frequently asked questions

What is 2-Bromo-1-(4-chloro-2-fluorophenyl)ethanone used for in organic synthesis?

It is primarily used as an electrophilic α-bromoketone building block. Researchers use it for the synthesis of thiazoles, imidazoles, and other pharmacologically relevant heterocycles via condensation with thioamides or amidines, as well as for N-, S-, and O-alkylation reactions. The fluorine and chlorine substituents on the ring provide additional handles for further functionalization.

How should 2-Bromo-1-(4-chloro-2-fluorophenyl)ethanone be stored to maintain stability?

The compound should be stored in a tightly sealed container under cool, dry, and dark conditions, away from moisture and incompatible reagents such as strong bases and reducing agents. Refrigerated storage at 2–8 °C is generally recommended for long-term preservation. Always refer to the Certificate of Analysis and Safety Data Sheet for lot-specific recommendations.

What safety precautions are required when handling this compound?

As an α-bromoketone, this compound is a lachrymator and a skin and mucous membrane irritant. Handling must be performed in a well-ventilated fume hood with appropriate PPE including nitrile gloves, a lab coat, and safety glasses. Avoid inhalation of dust or vapors. Consult the Aladdin Scientific Safety Data Sheet before use for full hazard information and first-aid procedures.

How can I obtain a Certificate of Analysis (CoA) for SKU B590003?

Certificates of Analysis for 2-Bromo-1-(4-chloro-2-fluorophenyl)ethanone (SKU B590003) can be requested through the Aladdin Scientific website using your lot number, or by contacting our customer service team directly. Each shipment is accompanied by lot-specific analytical data confirming purity and identity.

Is 2-Bromo-1-(4-chloro-2-fluorophenyl)ethanone compatible with palladium-catalyzed cross-coupling reactions?

The aryl chloride moiety present in the molecule can in principle serve as a substrate for palladium-catalyzed cross-coupling reactions such as Suzuki–Miyaura or Buchwald–Hartwig amination, typically requiring optimized catalyst systems due to the lower reactivity of aryl chlorides relative to aryl bromides. The alpha-bromoketone functionality is generally incompatible with the basic conditions used in many cross-coupling protocols and may require protective strategies or sequential functionalization. Specific conditions should be validated experimentally.

References

1. March, J.; Smith, M. B. March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 6th ed.; Wiley: Hoboken, NJ, 2007. (General reference for α-haloketone reactivity and nucleophilic substitution.)
2. Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed.; Oxford University Press: Oxford, 2012. (Textbook-level treatment of halogenated ketones and heterocycle synthesis.)
3. Aladdin Scientific product page for 2-Bromo-1-(4-chloro-2-fluorophenyl)ethanone, SKU B590003. (Internal source; purity and specifications are lot-dependent — consult CoA.)

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