2-bromo-4-(tert-butyl)pyridine | CAS 50488-34-1

PRODUCT NAME

2-Bromo-4-(tert-Butyl)pyridine
CAS Number: 50488-34-1

OVERVIEW

2-bromo-4-(tert-butyl)pyridine | CAS 50488-34-1  is a synthetically valuable heterocyclic intermediate featuring a bromine substituent at the 2-position of the pyridine ring and a bulky tert-butyl group at the 4-position. This compound plays an important role in medicinal chemistry, agrochemical synthesis, and materials science as a building block for further functionalization. Its unique substitution pattern endows it with distinct reactivity that is exploited in cross-coupling reactions, nucleophilic aromatic substitutions, and transition-metal catalyzed transformations.

CHEMICAL IDENTITY

• IUPAC Name: 2-Bromo-4-(tert-butyl)pyridine

• CAS Registry Number: 50488-34-1

• Molecular Formula: C10H12BrN

• Molecular Weight: 214.11 g/mol

• Structure Type: Substituted pyridine with halogen and tert-butyl functionalities

KEY FEATURES & ADVANTAGES

Synthetic Versatility

The presence of a bromine atom on a heteroaromatic ring makes this compound an excellent substrate for a wide range of cross-coupling reactions, such as Suzuki–Miyaura, Negishi, and Stille couplings. These transformations allow the efficient construction of C–C bonds, which is central to the synthesis of complex heterocyclic frameworks used in drug discovery.

Functional Group Compatibility

The 4-tert-butyl substituent provides steric hindrance, which can influence regioselectivity in subsequent reactions and improve stability under certain conditions. This attribute is particularly valuable when designing molecules that require selective reactivity or are prone to side reactions.

Applicability in Medicinal Chemistry

Heterocyclic scaffolds like substituted pyridines are ubiquitous in pharmaceutical research. 2-Bromo-4-(tert-butyl)pyridine serves as a precursor in the synthesis of novel small molecules targeting enzymes, receptors, and other biologically relevant macromolecules.

Agrochemical & Material Science Relevance

Beyond pharmaceuticals, derivatives of this building block are also explored in agrochemical development and advanced materials, including organic electronics and coordination polymers.

APPLICATIONS  of  2-bromo-4-(tert-butyl)pyridine | CAS 50488-34-1

1. Cross-Coupling Chemistry

2-Bromo-4-(tert-butyl)pyridine is frequently employed as an electrophilic partner in palladium and nickel catalyzed cross-coupling reactions. These methodologies enable the installation of diverse substituents, such as aryl, alkenyl, and alkynyl groups, expanding the utility of the core pyridine structure.

2. Heterocyclic Synthesis

This intermediate can be incorporated into multistep syntheses of more complex heterocyclic systems. It offers an entry point to fused ring systems, azaheterocycles, and polyfunctional derivatives that find use across chemical industries.

3. Lead Optimization in Drug Discovery

During lead optimization campaigns, variations on the pyridine ring often impact physicochemical properties such as lipophilicity, solubility, and metabolic stability. The tert-butyl group, in particular, is known to modulate these properties in drug candidates, making this intermediate particularly attractive.

4. Ligand and Catalyst Development

Functionalized pyridines serve as ligands or ligand precursors in homogeneous catalysis. The distinct steric and electronic characteristics of 2-Bromo-4-(tert-butyl)pyridine may be leveraged to design tailored ligand environments.

QUALITY & SPECIFICATIONS

ResolveMass Laboratories Inc. adheres to stringent quality control protocols to ensure that 2-Bromo-4-(tert-butyl)pyridine meets or exceeds industry standards. Each batch is subjected to analytical verification, including:

• NMR Spectroscopy (1H/13C)

• Gas Chromatography (GC)

• High-Performance Liquid Chromatography (HPLC)

• Mass Spectrometry (MS)

These analyses confirm structural integrity, purity, and consistency to support your research requirements.

PACKAGING OPTIONS

We offer flexible packaging solutions to accommodate varying project scales—ranging from gram quantities for early-stage research to multi-kilogram lots for process development. (Note: Packaging information can be tailored to your exact inventory and offerings.)

CUSTOM SYNTHESIS SERVICES

ResolveMass Laboratories Inc. also offers custom synthesis solutions. If your project requires variant derivatives, scale-up, or route optimization utilizing 2-Bromo-4-(tert-butyl)pyridine, our experienced team can collaborate on tailored chemical development strategies.

CONCLUSION

2-Bromo-4-(tert-butyl)pyridine (CAS 50488-34-1) is a high-value heterocyclic intermediate with broad applicability in organic synthesis, medicinal chemistry, and advanced materials research. With robust quality control and flexible supply options, ResolveMass Laboratories Inc. is your trusted partner for premium research chemicals.