5-Bromo-4-methylnicotinaldehyde: Properties & Lab Use FAQ

5-Bromo-4-methylnicotinaldehyde is a brominated, methyl-substituted pyridinecarboxaldehyde that serves as a versatile heterocyclic building block in medicinal chemistry and pharmaceutical synthesis.

CAS Number

Verify with Aladdin product datasheet (B192927)

Molecular Formula

C7H6BrNO

Molecular Weight

200.03 g/mol (nominal; verify on datasheet)

Functional Groups

Aldehyde (CHO), bromo substituent, methyl group, pyridine ring

Primary Application

Heterocyclic building block for drug discovery and synthesis of bioactive molecules

Storage Conditions

Store in a cool, dry, well-ventilated area away from light and moisture (verify SDS)

Chemical Identity and Structure

5-Bromo-4-methylnicotinaldehyde is a pyridine-based aldehyde bearing three key substituents on the aromatic ring: a bromine atom at the 5-position, a methyl group at the 4-position, and an aldehyde (–CHO) at the 3-position (nicotinaldehyde backbone). Its molecular formula is C₇H₆BrNO with a nominal molecular weight of approximately 200.03 g/mol. The combination of an electron-withdrawing bromine, an electron-donating methyl group, and a reactive aldehyde on the pyridine scaffold makes this compound a highly functional intermediate for further chemical elaboration. The ring nitrogen and the aldehyde provide two distinct handles for coordination chemistry and condensation reactions, respectively.

Synthetic Applications and Reactivity

The aldehyde group of 5-Bromo-4-methylnicotinaldehyde readily participates in a broad range of transformations, including reductive amination, Wittig olefination, Knoevenagel condensation, and imine/Schiff base formation, making it valuable for building complex nitrogen-containing scaffolds. The C–Br bond at the 5-position is well suited to palladium-catalyzed cross-coupling reactions such as Suzuki–Miyaura, Negishi, and Buchwald–Hartwig couplings, enabling introduction of aryl, heteroaryl, or amino groups with high selectivity. The methyl substituent at the 4-position can be further oxidized or functionalized if required. This multifunctionality positions the compound as a convergent building block in fragment-based drug design and multi-step total synthesis.

Handling, Safety, and Storage

As with most organobromine aldehydes, 5-Bromo-4-methylnicotinaldehyde should be handled with appropriate personal protective equipment (PPE), including nitrile gloves, safety glasses, and a laboratory coat. Work should be conducted in a fume hood to avoid inhalation of dust or vapors. The compound should be stored in a tightly sealed container in a cool, dry, and dark environment to prevent decomposition of the aldehyde functionality and to minimize moisture uptake. Specific hazard classifications, GHS pictograms, first-aid measures, and disposal requirements are detailed in the Safety Data Sheet (SDS) available from Aladdin Scientific for SKU B192927. Always consult the SDS before first use.

Purity, Quality, and Ordering Information

Aladdin Scientific offers 5-Bromo-4-methylnicotinaldehyde under SKU B192927. Purity specifications and analytical data (such as HPLC purity, NMR confirmation, and certificate of analysis) are available on the product page or upon request from technical support. Researchers are encouraged to confirm the current purity grade, available pack sizes, and pricing through the Aladdin website or by contacting customer service. For bulk or custom quantities, procurement teams should inquire about volume pricing and lead times. Proper documentation, including CoA and SDS, is provided with each shipment.

Quality Assurance and Regulatory Considerations

Each lot of 5-Bromo-4-methylnicotinaldehyde (B192927) from Aladdin Scientific is tested against internal quality specifications before release. A Certificate of Analysis (CoA) documenting lot-specific analytical results is available for every batch. For researchers working under GLP or GMP frameworks, or those requiring regulatory documentation for IND filings, it is advisable to contact Aladdin's technical or regulatory affairs team to discuss available documentation and compliance support. Export control and import regulations for brominated organic compounds may apply depending on jurisdiction; procurement managers should verify applicable regulations before international ordering.

Frequently asked questions

What is the molecular formula and molecular weight of 5-Bromo-4-methylnicotinaldehyde?

5-Bromo-4-methylnicotinaldehyde has the molecular formula C7H6BrNO and a nominal molecular weight of approximately 200.03 g/mol. Always confirm the exact value against the Certificate of Analysis (CoA) provided with SKU B192927, as lot-specific data may vary slightly.

What cross-coupling reactions can be performed using the bromo substituent of 5-Bromo-4-methylnicotinaldehyde?

The aryl C–Br bond at the 5-position is well suited for palladium-catalyzed cross-coupling reactions, including Suzuki–Miyaura (with boronic acids), Negishi (with organozinc reagents), Stille (with organotin reagents), and Buchwald–Hartwig amination reactions. These transformations enable efficient introduction of diverse aryl, heteroaryl, vinyl, or amino groups to expand molecular complexity. Optimization of catalyst, ligand, base, and solvent conditions is recommended for each specific coupling.

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

This compound should be stored in a tightly sealed container under cool, dry, and dark conditions to protect the aldehyde functional group from oxidation and moisture-induced degradation. Refrigerated storage (2–8 °C) is commonly recommended for sensitive aldehydes, but please confirm the exact recommended storage temperature in the Aladdin SDS and CoA for B192927. Avoid prolonged exposure to air, light, or humid environments.

What are the primary synthetic uses of the aldehyde group in 5-Bromo-4-methylnicotinaldehyde?

The aldehyde group enables a wide array of reactions including reductive amination to generate secondary amines, Wittig or HWE olefination for vinyl extensions, Knoevenagel condensation with active methylene compounds, and Schiff base formation with primary amines. These reactions make the aldehyde a versatile handle for constructing complex pharmacophores and heterocyclic drug-like scaffolds in medicinal chemistry programs.

How do I obtain a Certificate of Analysis (CoA) or Safety Data Sheet (SDS) for B192927?

CoA and SDS documents for 5-Bromo-4-methylnicotinaldehyde (SKU B192927) can be obtained directly from the Aladdin Scientific product page on the website by entering the lot number, or by contacting Aladdin customer service or technical support. These documents provide lot-specific purity data, analytical methods, hazard classifications, and handling instructions essential for safe and compliant laboratory use.

Is 5-Bromo-4-methylnicotinaldehyde suitable for use as a pharmaceutical intermediate?

Yes, the compound's combination of a reactive aldehyde, a halogen handle for cross-coupling, and a nitrogen-containing pyridine ring makes it well suited as a building block in pharmaceutical intermediate synthesis and drug discovery. However, its suitability for GMP or regulated pharmaceutical manufacturing must be assessed based on required purity grades, documentation, and compliance standards. Contact Aladdin Scientific to discuss research-grade versus higher-grade material availability.

References

1. Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed.; Oxford University Press: Oxford, 2012. (General reference for aldehyde reactivity and cross-coupling reactions.)
2. Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Palladium-Catalyzed Cross-Coupling Reactions in Total Synthesis. Angew. Chem. Int. Ed. 2005, 44, 4442–4489. doi:10.1002/anie.200500368
3. Aladdin Scientific. Product Page: 5-Bromo-4-methylnicotinaldehyde, SKU B192927. Safety Data Sheet and Certificate of Analysis available upon request.

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