5-Bromo-2-fluoro-3-methoxypyridine: Properties & Lab FAQ

5-Bromo-2-fluoro-3-methoxypyridine is a multifunctional halogenated pyridine building block widely used in medicinal chemistry and drug discovery as a versatile intermediate for the synthesis of complex heterocyclic scaffolds.

Chemical Name

5-Bromo-2-fluoro-3-methoxypyridine

Aladdin SKU

B590497

Molecular Formula

C6H5BrFNO

Molecular Weight

206.01 g/mol

Key Functional Groups

Bromo, fluoro, and methoxy substituents on a pyridine ring

Primary Application

Intermediate in medicinal chemistry, cross-coupling reactions, and SNAr chemistry

Chemical Identity and Structure

5-Bromo-2-fluoro-3-methoxypyridine (SKU: B590497) is a trisubstituted pyridine derivative bearing a bromine atom at the 5-position, a fluorine atom at the 2-position, and a methoxy group at the 3-position. Its molecular formula is C6H5BrFNO with a molecular weight of approximately 206.01 g/mol. The combination of halogen and methoxy substituents on the electron-deficient pyridine ring confers unique electronic properties, making the molecule highly reactive in both metal-catalyzed cross-coupling reactions and nucleophilic aromatic substitution (SNAr) chemistry. The fluorine at the 2-position is particularly activated toward SNAr due to the adjacent ring nitrogen, while the bromine at the 5-position serves as a handle for palladium-catalyzed transformations such as Suzuki–Miyaura, Negishi, and Buchwald–Hartwig couplings.

Applications in Synthesis and Drug Discovery

This compound serves as a versatile building block in pharmaceutical and agrochemical research. Its dual electrophilic sites allow sequential functionalization strategies: the C–F bond can be selectively displaced by nitrogen, oxygen, or sulfur nucleophiles under mild conditions, while the C–Br bond participates in transition-metal-catalyzed coupling reactions. Researchers commonly employ 5-Bromo-2-fluoro-3-methoxypyridine in the construction of pyridine-containing drug candidates, kinase inhibitor scaffolds, and biologically active heterocyclic libraries. The methoxy group can also be manipulated, for example via demethylation to reveal a free hydroxyl group or via directed ortho-metalation strategies to install additional substituents.

Handling, Storage, and Safety

5-Bromo-2-fluoro-3-methoxypyridine should be handled with standard laboratory precautions appropriate for halogenated organic compounds. Use appropriate personal protective equipment (PPE) including nitrile gloves, safety goggles, and a laboratory coat. Work in a well-ventilated fume hood to minimize inhalation exposure. The compound should be stored in a tightly sealed container in a cool, dry place away from moisture and incompatible materials such as strong oxidizers and strong bases. Refer to the Safety Data Sheet (SDS) supplied by Aladdin Scientific for complete hazard classification, first-aid measures, and disposal guidance before use. Molecular weight and physical state data should be confirmed against the current SDS and certificate of analysis (CoA).

Purity, Specifications, and Quality Assurance

Aladdin Scientific's B590497 is offered as a research-grade reagent. Customers are advised to request the Certificate of Analysis (CoA) for each lot to verify purity (typically assessed by GC or HPLC), identity (confirmed by NMR and/or MS), and appearance. Lot-specific data ensure that the reagent meets the requirements of sensitive downstream applications such as asymmetric catalysis, high-throughput screening, or API intermediate synthesis. If a specific purity grade is required for your application, please contact Aladdin Scientific's technical support team to discuss available grades and custom quantities.

Ordering and Availability

5-Bromo-2-fluoro-3-methoxypyridine is available from Aladdin Scientific under SKU B590497. To place an order, visit the Aladdin Scientific website, search by SKU or product name, and select your desired pack size and quantity. For bulk orders, custom packaging, or questions about lead times, contact Aladdin Scientific's sales or customer service team directly. Researchers requiring a formal quotation for procurement purposes may request one through the website or by email. Stock availability is subject to change; please check the product page for real-time inventory status.

Frequently asked questions

What is 5-Bromo-2-fluoro-3-methoxypyridine used for in the laboratory?

5-Bromo-2-fluoro-3-methoxypyridine is primarily used as a synthetic building block in medicinal chemistry and drug discovery. The C–Br bond is amenable to palladium-catalyzed cross-coupling reactions (e.g., Suzuki, Buchwald–Hartwig), while the C–F bond at the 2-position is activated toward nucleophilic aromatic substitution (SNAr) by nitrogen, oxygen, or sulfur nucleophiles. These orthogonal reactivities allow researchers to elaborate the scaffold sequentially into complex drug-like molecules.

How should 5-Bromo-2-fluoro-3-methoxypyridine be stored to maintain its stability?

The compound should be stored in a tightly sealed container under cool, dry conditions, away from light, moisture, and incompatible substances such as strong oxidizers and strong bases. Always consult the current Safety Data Sheet (SDS) and Certificate of Analysis (CoA) provided by Aladdin Scientific for lot-specific storage recommendations. Proper storage helps preserve purity and prevents degradation over the shelf life of the reagent.

What is the Aladdin Scientific SKU for 5-Bromo-2-fluoro-3-methoxypyridine, and how can I order it?

The Aladdin Scientific SKU for 5-Bromo-2-fluoro-3-methoxypyridine is B590497. You can order it directly through the Aladdin Scientific website by searching for the SKU or product name and selecting your required pack size. For bulk quantities, custom packaging, or formal quotations, please contact the Aladdin Scientific sales or customer service team.

Can the fluorine and bromine substituents be functionalized independently?

Yes. The two halogen substituents in 5-Bromo-2-fluoro-3-methoxypyridine exhibit orthogonal reactivity. The fluorine at the 2-position is selectively activated toward SNAr reactions due to the electron-withdrawing effect of the adjacent ring nitrogen, while the bromine at the 5-position is preferentially engaged by palladium or other transition-metal catalysts in cross-coupling reactions. Careful selection of reaction conditions allows selective transformation of each site.

Where can I find the Certificate of Analysis (CoA) and Safety Data Sheet (SDS) for B590497?

The Certificate of Analysis and Safety Data Sheet for B590497 (5-Bromo-2-fluoro-3-methoxypyridine) are available on the Aladdin Scientific product page for this SKU. You can download them directly from the website or contact Aladdin Scientific customer service to request lot-specific documentation. Always review these documents before handling the compound to ensure safe and compliant use in your laboratory.

References

1. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley-Interscience. General reference for SNAr and cross-coupling reaction principles.
2. Miyaura, N.; Suzuki, A. Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds. Chemical Reviews, 1995, 95, 2457–2483. General reference for Suzuki–Miyaura coupling applicable to aryl bromides. doi:10.1021/cr00039a007
3. Aladdin Scientific Product Page: 5-Bromo-2-fluoro-3-methoxypyridine, SKU B590497. Aladdin Scientific. Retrieved from https://www.aladdin-e.com.

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