5-Bromo-4-methoxypicolinonitrile: Properties & Lab FAQ

5-Bromo-4-methoxypicolinonitrile is a halogenated, methoxy-substituted pyridine-2-carbonitrile that serves as a versatile electrophilic building block in heterocyclic and medicinal chemistry synthesis.

Chemical Name

5-Bromo-4-methoxypicolinonitrile

SKU / Product Code

B734101

Molecular Formula

C7H5BrN2O

Core Functional Groups

Nitrile (CN), Bromo (Br), Methoxy (OCH3), Pyridine ring

Primary Application

Electrophilic building block for cross-coupling, nucleophilic aromatic substitution, and heterocyclic synthesis

Supplier

Aladdin Scientific

What Is 5-Bromo-4-methoxypicolinonitrile?

5-Bromo-4-methoxypicolinonitrile is a substituted pyridine heterocycle bearing three distinct functional handles: a nitrile group at the 2-position, a bromine atom at the 5-position, and a methoxy group at the 4-position. This combination of electron-withdrawing (CN) and moderate electron-donating (OCH3) substituents on the pyridine ring creates a polarized aromatic system suitable for a broad range of synthetic transformations.

The compound is catalogued by Aladdin Scientific under SKU B734101 and is intended for research use in synthetic organic and medicinal chemistry laboratories.

Key Chemical Properties and Structure

The pyridine ring nitrogen, combined with the electron-withdrawing nitrile at the 2-position, renders the ring strongly electron-deficient. This facilitates nucleophilic aromatic substitution (SNAr) at positions activated by the ring nitrogen and the CN group. The bromine at the 5-position is an excellent handle for palladium-catalyzed cross-coupling reactions, including Suzuki–Miyaura, Negishi, and Buchwald–Hartwig couplings.

The methoxy group at the 4-position can itself be displaced under forcing SNAr conditions when a superior nucleophile is present, offering an additional site for diversification. Researchers should be aware that the electronic balance between the OCH3 and CN groups dictates regioselectivity in substitution reactions.

Note: Specific physical constants such as melting point, exact molecular weight, and purity specification are not included in the available source material and should be confirmed from the product's Certificate of Analysis (CoA) available from Aladdin Scientific.

Handling, Storage, and Safety Considerations

As with most halogenated nitrile-containing heterocycles, 5-Bromo-4-methoxypicolinonitrile should be handled with appropriate personal protective equipment (PPE), including nitrile gloves, safety glasses, and a laboratory coat. Work should be conducted in a well-ventilated area or fume hood.

For storage, the compound should be kept in a tightly sealed container away from moisture, heat, and light. Refrigerated storage (2–8 °C) or freezer conditions are commonly recommended for halogenated nitrile building blocks to maintain long-term stability, but researchers should refer to the specific storage conditions stated on the product label and CoA supplied with SKU B734101.

Disposal must comply with local regulations for halogenated organic compounds. Always consult the Safety Data Sheet (SDS) before first use.

Synthetic Applications in Medicinal and Heterocyclic Chemistry

5-Bromo-4-methoxypicolinonitrile is valued in drug discovery and synthetic chemistry programs as a multi-functional scaffold. Its principal utility includes:

• Palladium-catalyzed cross-coupling: The C–Br bond at the 5-position undergoes efficient Suzuki, Negishi, Stille, and related couplings to introduce aryl, heteroaryl, vinyl, or alkyl groups, expanding molecular diversity.
• Nucleophilic aromatic substitution (SNAr): The activated ring system supports displacement reactions with amines, alkoxides, and thiolates, enabling rapid analog synthesis.
• Nitrile group elaboration: The CN group can be hydrolyzed to carboxylic acids or amides, reduced to amines, or converted to tetrazoles and other heterocycles, providing further diversification pathways.
• Fragment-based drug design: The compact, polar, and drug-like pyridine-nitrile core is attractive for fragment screening and lead optimization in target-based drug discovery programs.

These attributes make B734101 a broadly applicable building block for synthesis of kinase inhibitors, agrochemical leads, and other bioactive molecules.

Ordering and Quality Information

5-Bromo-4-methoxypicolinonitrile is available from Aladdin Scientific under SKU B734101. Researchers and procurement teams can place orders through the Aladdin Scientific website or by contacting customer service directly.

Each lot is supplied with documentation including a Certificate of Analysis (CoA) detailing purity, analytical data, and storage conditions. For custom quantities, bulk pricing, or specific purity requirements, please contact the Aladdin Scientific sales team. Refer to the Aladdin Scientific website for current stock availability, pricing, and applicable promotions.

For questions about returns, shipping, payment, or account management, please consult the relevant sections of the Aladdin Scientific Help Center or contact customer support.

Frequently asked questions

What is 5-Bromo-4-methoxypicolinonitrile used for in research?

5-Bromo-4-methoxypicolinonitrile is primarily used as a multifunctional building block in synthetic and medicinal chemistry. Its C–Br bond enables palladium-catalyzed cross-coupling reactions, the electron-deficient ring supports nucleophilic aromatic substitution, and the nitrile group can be further elaborated into amines, amides, acids, or heterocycles. These features make it valuable for the synthesis of drug candidates, agrochemical leads, and other bioactive heterocyclic compounds.

How should 5-Bromo-4-methoxypicolinonitrile be stored to maintain stability?

Halogenated nitrile heterocycles of this class are generally best stored in a tightly sealed container under cool, dry, and dark conditions; refrigerated (2–8 °C) or freezer storage is commonly recommended. However, the definitive storage conditions for SKU B734101 should be confirmed from the product label and Certificate of Analysis (CoA) provided by Aladdin Scientific, as specific requirements may vary by lot.

Can the methoxy group in 5-Bromo-4-methoxypicolinonitrile be substituted in SNAr reactions?

Yes, under appropriate nucleophilic aromatic substitution (SNAr) conditions, the methoxy group at the 4-position can be displaced by stronger nucleophiles such as amines or thiolates, because the electron-withdrawing nitrile and the ring nitrogen collectively activate that position toward substitution. Reaction conditions (solvent, temperature, nucleophile identity) must be optimized to achieve selective displacement of the methoxy group versus other transformations on the molecule.

What purity grade is available for SKU B734101 from Aladdin Scientific?

Specific purity data for SKU B734101 is not detailed in the available source material. Researchers should request or download the current Certificate of Analysis (CoA) from the Aladdin Scientific product page or contact customer service to confirm the purity grade and analytical data for the current lot before use in sensitive applications.

Is 5-Bromo-4-methoxypicolinonitrile suitable for Suzuki–Miyaura cross-coupling?

Yes, the aryl C–Br bond at the 5-position of 5-Bromo-4-methoxypicolinonitrile is well-suited for Suzuki–Miyaura cross-coupling with arylboronic acids and boronate esters under standard palladium catalysis conditions. The electron-deficient nature of the pyridine ring can facilitate oxidative addition and generally leads to efficient coupling under mild conditions, though specific conditions should be optimized empirically for each substrate combination.

References

1. Aladdin Scientific product page for 5-Bromo-4-methoxypicolinonitrile, SKU B734101.
2. General reference: Miyaura, N.; Suzuki, A. Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds. Chemical Reviews, 1995. (Foundational reference for Suzuki–Miyaura coupling methodology.) doi:10.1021/cr00039a007
3. General reference: Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed. Oxford University Press, 2012. (Standard textbook reference for SNAr reactions and nitrile group transformations.)

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