Production Method 1

26218-78-0

1221127-57-6

869640-48-2

Reaction Conditions

1.1 Solvents: Tetrahydrofuran ;  5 min, rt
1.2 Solvents: Water ;  15 min, rt

Reference

Efficient synthesis of primary and secondary amides via reacting esters with alkali metal amidoboranes

Guo, Yu ; et al, Nature Communications, 2021, 12(1),

6-bromo-N-methyl-pyridine-3-carboxamide Raw materials

• methyl 6-bromopyridine-3-carboxylate
• Sodium methylaminotrihydroborate

6-bromo-N-methyl-pyridine-3-carboxamide Preparation Products

• 6-bromo-N-methyl-pyridine-3-carboxamide (869640-48-2)

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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyridines and derivatives Pyridinecarboxamides
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyridines and derivatives Pyridinecarboxylic acids and derivatives Pyridinecarboxamides

Comprehensive Overview of 6-bromo-N-methyl-pyridine-3-carboxamide (CAS No. 869640-48-2): Properties, Applications, and Industry Insights

6-bromo-N-methyl-pyridine-3-carboxamide (CAS No. 869640-48-2) is a specialized organic compound that has garnered significant attention in pharmaceutical and agrochemical research. This brominated pyridine derivative is characterized by its unique molecular structure, combining a pyridine ring with a carboxamide functional group and a bromine substituent. Its chemical formula, C₇H₇BrN₂O, and molecular weight of 215.05 g/mol make it a versatile intermediate in synthetic chemistry.

The compound's 6-bromo substitution and N-methyl carboxamide moiety contribute to its reactivity, enabling diverse applications in drug discovery and material science. Researchers particularly value its role as a building block for more complex molecules, especially in the development of kinase inhibitors and heterocyclic compounds. Recent studies highlight its potential in addressing challenges related to drug solubility and bioavailability, which are critical factors in modern pharmaceutical development.

In the context of current industry trends, 6-bromo-N-methyl-pyridine-3-carboxamide aligns with the growing demand for targeted therapeutics and precision medicine. Its structural features allow for selective interactions with biological targets, making it relevant to investigations into personalized treatment approaches. The compound's thermal stability (typically stable below 250°C) and moderate solubility in polar organic solvents further enhance its utility in laboratory settings.

From a synthetic chemistry perspective, the bromine atom at the 6-position serves as an excellent handle for further functionalization, enabling cross-coupling reactions such as Suzuki-Miyaura or Buchwald-Hartwig couplings. This characteristic has made CAS No. 869640-48-2 particularly valuable in medicinal chemistry workflows, where rapid diversification of molecular scaffolds is often required. The N-methyl group additionally influences the compound's metabolic stability, a crucial consideration in drug design.

Analytical characterization of 6-bromo-N-methyl-pyridine-3-carboxamide typically involves techniques such as HPLC (for purity assessment), NMR spectroscopy (for structural confirmation), and mass spectrometry (for molecular weight verification). The compound generally appears as a white to off-white crystalline powder with a purity specification of ≥95% in commercial offerings. Proper storage recommendations include protection from moisture at temperatures between 2-8°C in airtight containers.

The commercial availability of 6-bromo-N-methyl-pyridine-3-carboxamide has expanded in recent years, with suppliers offering quantities ranging from milligram to kilogram scales. This accessibility supports its growing application in high-throughput screening and combinatorial chemistry platforms. Pricing trends reflect the compound's specialized nature, with costs varying based on purity levels and order volumes.

Environmental and handling considerations for CAS No. 869640-48-2 follow standard laboratory safety protocols. While not classified as hazardous under most regulatory frameworks, prudent practices include using personal protective equipment and working in well-ventilated areas. The compound's ecological impact and biodegradability profile are subjects of ongoing research, particularly in light of increasing focus on green chemistry principles.

Future research directions for 6-bromo-N-methyl-pyridine-3-carboxamide may explore its potential in catalysis applications or as a precursor for functional materials. The compound's electronic properties, influenced by the electron-withdrawing bromine and electron-donating methyl group, suggest possible utility in organic electronics or photovoltaic materials. These emerging applications align with broader scientific interests in energy storage and renewable technologies.

For researchers seeking alternatives or derivatives, structurally related compounds include 6-chloro-N-methyl-pyridine-3-carboxamide or unsubstituted N-methyl-nicotinamide. Each variant offers distinct reactivity patterns and physical properties, allowing chemists to tailor their selection based on specific project requirements. The choice between bromo and chloro analogs often depends on the intended downstream transformations and desired electronic effects in the target molecule.

In summary, 6-bromo-N-methyl-pyridine-3-carboxamide (CAS No. 869640-48-2) represents a valuable tool in modern chemical research, bridging pharmaceutical development and materials science. Its balanced combination of reactivity and stability, coupled with straightforward functionalization potential, ensures its continued relevance in addressing contemporary scientific challenges. As research into heterocyclic chemistry advances, this compound will likely maintain its position as a key intermediate in innovative synthetic strategies.

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