3-Bromo-2-methoxypyridine: Properties, Uses & FAQ

3-Bromo-2-methoxypyridine is a halogenated heterocyclic building block widely employed in medicinal chemistry and organic synthesis as a versatile intermediate for cross-coupling reactions and the construction of complex pyridine-based frameworks.

Chemical Name

3-Bromo-2-methoxypyridine

SKU

B120788

Molecular Formula

C₆H₆BrNO

Molecular Weight

188.02 g/mol

CAS Number

13472-59-8

Functional Groups

Aryl bromide, methoxy, pyridine nitrogen

Primary Application

Cross-coupling reactions and heterocyclic synthesis

Chemical Identity and Structure

3-Bromo-2-methoxypyridine (CAS 13472-59-8, SKU B120788) is a pyridine derivative bearing a bromine substituent at the 3-position and a methoxy group at the 2-position of the ring. Its molecular formula is C₆H₆BrNO with a molecular weight of approximately 188.02 g/mol. The combination of an electron-donating methoxy group adjacent to the ring nitrogen and a reactive aryl C–Br bond in the ortho-like relationship makes this compound electronically distinctive among halopyridine building blocks. The molecule is typically a colorless to pale-yellow liquid or low-melting solid and is soluble in common organic solvents such as dichloromethane, THF, ethyl acetate, and DMSO.

Applications in Organic and Medicinal Chemistry

3-Bromo-2-methoxypyridine is primarily valued as an electrophilic coupling partner in transition-metal-catalyzed cross-coupling reactions. Key applications include:

• Suzuki–Miyaura coupling: The aryl bromide reacts with aryl- or heteroarylboronic acids in the presence of a palladium catalyst and base to build biaryl and heteroaryl frameworks common in drug candidates.
• Buchwald–Hartwig amination: The C–Br bond can be functionalized with amines under palladium catalysis, providing access to 3-amino-2-methoxypyridine analogues relevant to pharmaceutical targets.
• Negishi and Kumada couplings: Organozinc and Grignard reagents can be coupled at the 3-position to introduce diverse carbon substituents.
• Directed metalation: The methoxy group at C-2 can serve as a directed metalation group (DMG), enabling regioselective lithiation adjacent to it for further elaboration.
• Pharmaceutical intermediates: The 2-methoxypyridine motif appears in a number of biologically active scaffolds; introduction of the 3-bromo handle allows diversification toward kinase inhibitors, antibacterials, and CNS-active compounds.

Researchers should verify specific reaction conditions (catalyst loading, ligand, base, solvent, temperature) in peer-reviewed literature before scaling up reactions.

Handling, Storage, and Safety

While 3-Bromo-2-methoxypyridine is not classified among the most highly hazardous laboratory reagents, standard precautions for halogenated heterocyclic compounds should be observed:

• Personal protective equipment: Wear appropriate gloves (nitrile recommended), safety glasses, and a laboratory coat. Work in a well-ventilated fume hood.
• Storage: Store in a tightly sealed container in a cool, dry, well-ventilated area away from moisture, light, and incompatible materials such as strong oxidizers and strong bases. Refrigerated storage (2–8 °C) is typically recommended to maintain long-term stability.
• Stability: The compound is generally stable under recommended storage conditions. Prolonged exposure to air and moisture may lead to slow degradation.
• Disposal: Dispose of as halogenated organic waste in accordance with local, institutional, and national regulations.

Always consult the current Safety Data Sheet (SDS) provided by Aladdin Scientific for B120788 before use. SDS documents contain authoritative hazard, first-aid, and disposal information.

Purity, Specification, and Quality

Aladdin Scientific supplies 3-Bromo-2-methoxypyridine (B120788) to research-grade specifications. Typical quality attributes include:

• Purity: Confirmed by GC or HPLC analysis; research-grade material is typically ≥97% or ≥98% pure (verify the current CoA for the specific lot).
• Identity confirmation: Structural identity is verified by techniques such as ¹H NMR and/or GC-MS consistent with the expected molecular structure.
• Packaging: Available in multiple quantities to suit screening, scale-up, and production needs. Packaging is designed to protect the compound from moisture and light during shipping and storage.
• Lot-specific certificates of analysis (CoA): Available upon request or via the Aladdin Scientific website using the lot number printed on the label.

If your application requires higher purity or custom specifications, please contact Aladdin Scientific's technical support team for guidance.

Ordering and Customer Support

3-Bromo-2-methoxypyridine is available from Aladdin Scientific under SKU B120788. To place an order or obtain more information:

• Search for B120788 on the Aladdin Scientific website to view current pricing, available pack sizes, and stock status.
• For bulk or custom quantity inquiries, contact our sales team directly via the website inquiry form or customer service email.
• Technical questions about applications, compatibility, or reaction conditions can be directed to Aladdin Scientific's technical support.
• Certificates of Analysis (CoA) and Safety Data Sheets (SDS) are downloadable from the product page or available upon request.
• Expedited shipping options may be available depending on your region; consult shipping and delivery policies on the Aladdin website for details.

Frequently asked questions

What is 3-Bromo-2-methoxypyridine used for in chemical synthesis?

3-Bromo-2-methoxypyridine is primarily used as a building block in transition-metal-catalyzed cross-coupling reactions such as Suzuki–Miyaura, Buchwald–Hartwig, Negishi, and Kumada couplings, where the aryl C–Br bond serves as the electrophilic partner. It is also exploited in directed metalation strategies and as an intermediate for the synthesis of biologically active heterocyclic scaffolds, including pharmaceutical candidates targeting kinases and CNS pathways.

How should 3-Bromo-2-methoxypyridine (B120788) be stored to maintain its stability?

The compound should be stored in a tightly sealed container in a cool, dry, and well-ventilated area, away from moisture, light, and strong oxidizers or strong bases. Refrigerated storage at 2–8 °C is typically recommended for long-term preservation. Always refer to the current Safety Data Sheet and Certificate of Analysis from Aladdin Scientific for lot-specific storage guidance.

What purity grade is Aladdin Scientific's 3-Bromo-2-methoxypyridine, and how is purity verified?

Aladdin Scientific's B120788 is supplied as a research-grade reagent, typically with purity ≥97% or ≥98% as determined by GC or HPLC analysis. Structural identity is further confirmed by techniques such as ¹H NMR and/or GC-MS. Lot-specific Certificates of Analysis (CoA) are available on the product page or upon request, and customers should consult the CoA for their specific lot to confirm purity values.

Can 3-Bromo-2-methoxypyridine be used in Suzuki–Miyaura cross-coupling reactions?

Yes, 3-Bromo-2-methoxypyridine is well-suited as an aryl bromide electrophile in Suzuki–Miyaura cross-coupling reactions with aryl- or heteroarylboronic acids under palladium catalysis. The reaction typically requires a Pd(0) or Pd(II) precatalyst, an appropriate phosphine or N-heterocyclic carbene ligand, an inorganic base, and a polar solvent such as DMF, dioxane, or aqueous THF. Researchers should consult the primary literature to optimize conditions for their specific substrate pairing.

How do I obtain a Safety Data Sheet (SDS) or Certificate of Analysis (CoA) for B120788?

Safety Data Sheets and Certificates of Analysis for B120788 (3-Bromo-2-methoxypyridine) are available directly from the Aladdin Scientific product page. You can search for SKU B120788 on the Aladdin Scientific website and download documents from the product listing. Alternatively, contact Aladdin Scientific customer service with your lot number to request these documents by email.

References

1. Johansson Seechurn, C. C. C.; Kitching, M. O.; Colacot, T. J.; Snieckus, V. Cross-Coupling Technology: A Perspective on the Nobel Prize in Chemistry 2010. Angew. Chem. Int. Ed. 2012, 51, 5062–5085. doi:10.1002/anie.201107017
2. Hartwig, J. F. Evolution of a Fourth Generation Catalyst for the Amination and Thioetherification of Aryl Halides. Acc. Chem. Res. 2008, 41, 1534–1544. doi:10.1021/ar800098p
3. Snieckus, V. Directed ortho metalation. Tertiary amide and O-carbamate directors in synthetic strategies for polysubstituted aromatics. Chem. Rev. 1990, 90, 879–933. doi:10.1021/cr00104a001

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