2-Bromo-3-methoxy-6-methylpyridine: Properties & Lab FAQ

2-Bromo-3-methoxy-6-methylpyridine is a halogenated methoxypyridine building block widely employed in medicinal chemistry and organic synthesis as a versatile intermediate for constructing complex heterocyclic frameworks.

Chemical Name

2-Bromo-3-methoxy-6-methylpyridine

SKU / Catalog Number

B725307

Molecular Formula

C7H8BrNO

Molecular Weight

202.05 g/mol

Functional Class

Halogenated heteroaromatic building block

Supplier

Aladdin Scientific

Overview and Chemical Identity

2-Bromo-3-methoxy-6-methylpyridine (CAS not confirmed in source material; see review flags) is a substituted pyridine bearing three distinct functional handles: a C-2 bromine atom, a C-3 methoxy group, and a C-6 methyl group. This combination of substituents makes the molecule an attractive scaffold in synthetic chemistry. The bromine at the 2-position is highly amenable to transition-metal-catalysed cross-coupling reactions such as Suzuki–Miyaura, Negishi, and Buchwald–Hartwig couplings, enabling efficient C–C and C–N bond formation. The methoxy group at C-3 modulates the electron density of the ring and can participate in directed ortho-metalation strategies, while the methyl group at C-6 offers a handle for further functionalisation or influences the steric and electronic profile of the molecule.

Aladdin Scientific supplies this compound under SKU B725307 for research use.

Synthetic Applications and Reactivity

The primary synthetic utility of 2-Bromo-3-methoxy-6-methylpyridine lies in its reactivity at the C-2 bromo position. Key applications include:

• Palladium-catalysed cross-coupling: The aryl bromide undergoes Suzuki–Miyaura coupling with boronic acids and esters, Negishi coupling with organozinc reagents, and Sonogashira coupling with terminal alkynes to furnish biaryl and alkynyl pyridine products relevant to drug discovery programmes.
• Buchwald–Hartwig amination: Introduction of primary or secondary amines at C-2 yields 2-aminopyridine derivatives that are privileged scaffolds in kinase inhibitor design.
• Directed metalation: The methoxy group at C-3 can act as a directed metalation group (DMG) under appropriate strong-base conditions, allowing selective functionalisation at adjacent positions.
• Nucleophilic aromatic substitution: Under forcing conditions or with activated nucleophiles, displacement of the bromine may also be achieved.

These attributes collectively position 2-Bromo-3-methoxy-6-methylpyridine as a versatile intermediate in multi-step synthesis of bioactive heterocyclic compounds.

Handling, Storage and Safety

As with most organobromine heterocyclic compounds, appropriate laboratory precautions should be observed when working with 2-Bromo-3-methoxy-6-methylpyridine:

• Personal protective equipment (PPE): Wear nitrile gloves, safety glasses, and a lab 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, heat, and incompatible materials such as strong oxidising agents and strong bases. Typical storage temperature is 2–8 °C or room temperature as specified on the product label.
• Stability: The compound is expected to be stable under recommended storage conditions. Prolonged exposure to moisture or light may cause degradation over time.
• Disposal: Dispose of waste in accordance with local, regional, and national regulations governing halogenated organic compounds.

Always consult the Safety Data Sheet (SDS) supplied by Aladdin Scientific for product-specific hazard information before use.

Ordering and Specifications

2-Bromo-3-methoxy-6-methylpyridine is available from Aladdin Scientific under the following details:

• SKU: B725307
• Purity: Please refer to the current Certificate of Analysis (CoA) available on the Aladdin Scientific website for the lot-specific purity value.
• Pack sizes: Multiple pack sizes may be available; contact Aladdin Scientific sales or visit the product page for current stock and pricing.
• Lead time: Standard in-stock items typically ship within 1–3 business days; availability may vary by region.

For bulk or custom quantities, please contact the Aladdin Scientific sales team directly. A Certificate of Analysis and Safety Data Sheet are available upon request or can be downloaded from the product page.

Frequently asked questions

What is 2-Bromo-3-methoxy-6-methylpyridine used for in synthesis?

2-Bromo-3-methoxy-6-methylpyridine is primarily used as a building block in palladium-catalysed cross-coupling reactions (e.g., Suzuki–Miyaura, Negishi, Sonogashira) and Buchwald–Hartwig aminations, enabling efficient construction of functionalised pyridine derivatives. It is particularly valuable in medicinal chemistry for the preparation of pharmaceutical intermediates and bioactive heterocyclic compounds.

How should 2-Bromo-3-methoxy-6-methylpyridine be stored to ensure stability?

The compound should be stored in a tightly sealed container in a cool, dry, and well-ventilated location, protected from moisture, direct light, and heat sources. Refer to the Aladdin Scientific product label and SDS for the recommended storage temperature specific to your lot.

What is the catalog number for 2-Bromo-3-methoxy-6-methylpyridine at Aladdin Scientific?

2-Bromo-3-methoxy-6-methylpyridine is listed under SKU B725307 at Aladdin Scientific. You can search this SKU directly on the Aladdin Scientific website to access the product page, current pricing, stock status, and downloadable documentation.

Can the bromine in 2-Bromo-3-methoxy-6-methylpyridine be selectively replaced with other functional groups?

Yes. The C-2 bromine is well-suited for selective replacement via transition-metal-catalysed cross-coupling with various nucleophilic partners (boronic acids, amines, organozincs, alkynes) under mild to moderate conditions, while leaving the methoxy and methyl substituents intact. Reaction conditions should be optimised for the specific transformation and nucleophile used.

What safety precautions should I take when handling 2-Bromo-3-methoxy-6-methylpyridine?

Wear appropriate PPE including nitrile gloves, safety glasses, and a lab coat, and handle the compound in a fume hood. Avoid inhalation, ingestion, and skin or eye contact. Consult the Aladdin Scientific Safety Data Sheet (SDS) for full hazard information, first-aid measures, and disposal guidance before use.

References

1. General reference: March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 7th Edition. Smith, M. B. Wiley, 2013. [Textbook-level background on cross-coupling reactions and halopyridine reactivity]
2. Aladdin Scientific product page for 2-Bromo-3-methoxy-6-methylpyridine, SKU B725307. Aladdin Scientific.

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