2-Bromo-6-Fluorobenzoyl Chloride: Key Facts & FAQs

2-Bromo-6-fluorobenzoyl chloride is a halogenated aromatic acyl chloride widely used as a reactive electrophilic building block in pharmaceutical and fine-chemical synthesis.

Chemical Name

2-Bromo-6-fluorobenzoyl chloride

CAS Number

Needs review — not confirmed in source material

Molecular Formula

C₇H₃BrClFO

Molecular Weight

237.45 g/mol (calculated; verify against CoA)

Functional Class

Aromatic acyl chloride; electrophilic acylating agent

Key Substituents

Bromo at ortho position 2; Fluoro at ortho position 6; Acyl chloride at position 1

Aladdin SKU

B586158

Storage Recommendation

Store under inert atmosphere, cool and dry; away from moisture (verify with SDS)

What Is 2-Bromo-6-Fluorobenzoyl Chloride and What Is It Used For?

2-Bromo-6-fluorobenzoyl chloride (Aladdin SKU: B586158) is an ortho,ortho-disubstituted aromatic acyl chloride bearing both a bromine and a fluorine atom on the benzene ring flanking the carbonyl chloride group. This unique substitution pattern makes it a versatile bifunctional building block in organic synthesis.

The acyl chloride functionality reacts rapidly with nucleophiles such as amines, alcohols, and water to form amides, esters, and carboxylic acids, respectively, making it an efficient acylating agent. Simultaneously, the bromine substituent can participate in transition-metal-catalyzed cross-coupling reactions (e.g., Suzuki, Negishi, or Buchwald–Hartwig), while the fluorine substituent influences both electronic properties and metabolic stability of drug candidates.

Typical applications include: synthesis of pharmaceutical intermediates, preparation of agrochemical scaffolds, and construction of complex aromatic frameworks for material science research. Researchers should consult the current product specification sheet for confirmed purity and grade information.

Chemical and Physical Properties

As an aromatic acyl chloride, 2-bromo-6-fluorobenzoyl chloride possesses several important physicochemical characteristics that researchers should be aware of before use:

• Reactivity: The carbonyl chloride group is highly electrophilic and reacts vigorously with protic nucleophiles including water (hydrolysis), alcohols (esterification), and amines (amide bond formation). Reactions are typically exothermic.
• Steric effects: The two ortho substituents (Br and F) create significant steric crowding around the carbonyl, which can moderate reaction rates compared to less-hindered benzoyl chlorides and influence regio- and stereoselectivity in downstream transformations.
• Electronic effects: Fluorine is strongly electron-withdrawing by induction, while bromine exerts a moderate electron-withdrawing inductive effect. Together, these substituents modulate the electrophilicity of the carbonyl carbon and direct further electrophilic or nucleophilic reactions on the ring.
• Physical state: Expected to be a liquid or low-melting solid at room temperature; precise melting/boiling point data should be confirmed from the current product CoA or SDS.

Note: Specific numerical property values (boiling point, density, refractive index) are not confirmed in the available source material and have been flagged for review.

Safe Handling, Storage, and Disposal

Acyl chlorides are corrosive and moisture-sensitive reagents that require careful handling in a well-ventilated fume hood. The following general precautions apply to 2-bromo-6-fluorobenzoyl chloride; always consult the current Safety Data Sheet (SDS) supplied by Aladdin Scientific before use:

• Personal protective equipment (PPE): Wear chemical-resistant gloves, safety goggles, and a lab coat at all times. A face shield is recommended when handling larger quantities.
• Moisture protection: Keep strictly anhydrous. Contact with atmospheric moisture causes hydrolysis and generation of HCl and HBr gases, both of which are corrosive and irritating to the respiratory tract.
• Storage: Store in a tightly sealed container under an inert atmosphere (nitrogen or argon), in a cool, dry location away from incompatible materials such as bases, alcohols, and oxidizers. Recommended storage temperature should be confirmed from the SDS or product label.
• Spill response: Neutralize small spills with dry sodium bicarbonate; avoid water addition to pure acyl chloride. Collect waste in appropriate chemical waste containers.
• Disposal: Dispose of in accordance with local, national, and institutional regulations for halogenated organic waste. Do not pour down the drain.

Synthetic Applications and Reaction Guidance

2-Bromo-6-fluorobenzoyl chloride serves as a multifunctional reagent due to its three distinct reactive sites. Below is guidance on leveraging each site in synthetic workflows:

1. Acylation Reactions

The acyl chloride reacts with primary and secondary amines to give the corresponding benzamides, or with alcohols and phenols to give esters. Reactions are typically conducted in anhydrous conditions using a suitable base (e.g., triethylamine or pyridine) to scavenge the HCl generated. Common solvents include dichloromethane, tetrahydrofuran, and acetonitrile.

2. Cross-Coupling via the C–Br Bond

The aryl bromide is a competent partner in palladium-catalyzed cross-coupling reactions such as Suzuki–Miyaura (with boronic acids/esters), Negishi (with organozinc reagents), and Kumada couplings (with Grignard reagents). These transformations allow introduction of diverse aryl, heteroaryl, alkenyl, or alkyl groups at the 2-position.

3. Nucleophilic Aromatic Substitution via the C–F Bond

The fluorine atom at the 6-position can be displaced by suitable nucleophiles under nucleophilic aromatic substitution (SNAr) conditions, particularly when the ring is sufficiently electron-poor. This provides access to a range of 2-bromo-6-substituted benzoic acid derivatives after acyl chloride hydrolysis, or to corresponding benzamides if amines are used first.

Researchers are advised to validate specific reaction conditions in their own laboratories; the above guidance reflects general organic chemistry principles and should not be taken as guaranteed outcomes.

Ordering, Specifications, and Quality

Aladdin Scientific offers 2-bromo-6-fluorobenzoyl chloride under SKU B586158. Researchers and procurement personnel should be aware of the following when ordering:

• Purity and grade: Specific purity grades available for B586158 should be confirmed on the current Aladdin product page or by contacting customer service. Always request a Certificate of Analysis (CoA) to confirm lot-specific purity, water content, and any other critical specifications before use in sensitive applications.
• Pack sizes: Available pack sizes should be confirmed on the product listing. Contact Aladdin Scientific for bulk or custom quantity inquiries.
• Shipping and storage conditions: Due to its moisture sensitivity and corrosive nature, this reagent is shipped with appropriate hazmat packaging. Confirm temperature requirements and regulatory shipping classifications with Aladdin customer service prior to ordering, particularly for international shipments.
• Returns and quality issues: If the product does not meet specification, contact Aladdin Scientific customer service promptly with lot number and CoA details. Refer to Aladdin's return and refund policy for applicable procedures.
• Internal reference code: The source material references BD306980 as an internal descriptor; quote SKU B586158 when placing orders.

Frequently asked questions

What nucleophiles react with 2-bromo-6-fluorobenzoyl chloride, and under what conditions?

The acyl chloride group reacts readily with amines to form benzamides and with alcohols or phenols to form esters. Reactions are best performed under anhydrous conditions in solvents such as DCM or THF, with a tertiary amine base (e.g., Et₃N or DIPEA) to neutralize the HCl byproduct. Water will cause rapid hydrolysis to the corresponding carboxylic acid.

Can the aryl bromide in 2-bromo-6-fluorobenzoyl chloride be used in palladium-catalyzed cross-coupling reactions?

Yes. The C–Br bond is a suitable electrophilic partner for palladium-catalyzed cross-coupling reactions, including Suzuki–Miyaura coupling with boronic acids and Negishi coupling with organozinc reagents. Researchers should protect or pre-react the acyl chloride group (e.g., convert to an amide or ester) before subjecting the molecule to aqueous cross-coupling conditions to avoid hydrolysis.

How should I store 2-bromo-6-fluorobenzoyl chloride to maintain its quality?

Store in a tightly sealed container under an inert atmosphere (nitrogen or argon) in a cool, dry place away from moisture, bases, and alcohols. Exposure to moisture causes hydrolysis and degradation. Always reseal the container promptly after use. Specific temperature recommendations should be confirmed from the product SDS or CoA provided by Aladdin Scientific.

What is the significance of having both bromine and fluorine substituents on the benzene ring?

The two halogens serve complementary synthetic roles: the bromine at the 2-position enables further functionalization via transition-metal-catalyzed cross-coupling, while the fluorine at the 6-position can be displaced by SNAr or retained to modulate the electronic and pharmacokinetic properties of target molecules. Together with the acyl chloride handle, this makes the compound a highly versatile three-point diversification scaffold for medicinal chemistry and agrochemical research.

Is 2-bromo-6-fluorobenzoyl chloride available in different purity grades from Aladdin Scientific?

Available purity grades and pack sizes for SKU B586158 should be confirmed directly on the Aladdin Scientific product page or by contacting the Aladdin customer service team. Requesting a Certificate of Analysis (CoA) for the specific lot you receive is always recommended to verify purity before use in critical experiments.

References

1. General reference: March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley. (Acyl chloride reactivity and nucleophilic acyl substitution — textbook-level fact, no specific edition confirmed in source material.)
2. General reference: Miyaura, N.; Suzuki, A. Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds. Chemical Reviews, 1995. (Suzuki–Miyaura coupling — textbook-level fact cited for context; specific applicability to this substrate needs experimental confirmation.)
3. Aladdin Scientific product listing: 2-Bromo-6-fluorobenzoyl chloride, SKU B586158. Internal reference BD306980. (Primary source for product identity; no additional bibliographic data available in source material.)

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