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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyridines and derivatives 2-halopyridines
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyridines and derivatives Halopyridines 2-halopyridines

Introduction to 2-Bromo-5-cyclopropylpyridine (CAS No. 1142197-14-5)

2-Bromo-5-cyclopropylpyridine, identified by the Chemical Abstracts Service Number (CAS No.) 1142197-14-5, is a significant intermediate in modern pharmaceutical and agrochemical research. This compound belongs to the pyridine class of heterocyclic aromatic compounds, characterized by a nitrogen atom embedded within a six-membered ring structure. The presence of both bromine and cyclopropyl substituents makes it a versatile building block for synthesizing more complex molecules, particularly in medicinal chemistry.

The bromine atom at the 2-position and the cyclopropyl group at the 5-position introduce unique electronic and steric properties to the molecule. These functional groups enhance its reactivity, making it valuable for further chemical transformations such as cross-coupling reactions, nucleophilic substitutions, and other synthetic pathways. The compound’s structural features are particularly useful in designing novel bioactive molecules with potential therapeutic applications.

In recent years, 2-Bromo-5-cyclopropylpyridine has garnered attention in the development of small-molecule drugs targeting various diseases. Its incorporation into drug candidates has shown promise in modulating biological pathways associated with cancer, inflammation, and infectious diseases. The cyclopropyl group, in particular, has been identified as a key structural motif that can improve drug-like properties such as solubility, metabolic stability, and binding affinity to biological targets.

One of the most compelling aspects of 2-Bromo-5-cyclopropylpyridine is its role in constructing kinase inhibitors. Kinases are enzymes involved in numerous cellular processes, and their dysregulation is often linked to diseases like cancer. By leveraging the reactivity of the bromine atom for palladium-catalyzed cross-coupling reactions, researchers can efficiently append various pharmacophores to the pyridine core. This approach has led to the discovery of several potent kinase inhibitors that are currently undergoing preclinical evaluation.

Moreover, the compound’s utility extends beyond pharmaceuticals into agrochemical research. Its structural framework is being explored as a precursor for developing novel pesticides and herbicides. The combination of bromine and cyclopropyl substituents allows for modifications that enhance bioactivity against pests while maintaining environmental safety profiles.

The synthesis of 2-Bromo-5-cyclopropylpyridine typically involves multi-step organic reactions starting from commercially available pyridine derivatives. Key steps include halogenation at the desired positions followed by protection-deprotection strategies to introduce the cyclopropyl group. Advances in synthetic methodologies have improved both yield and purity, making it more accessible for industrial-scale applications.

Recent studies have highlighted the importance of regioselectivity in incorporating substituents onto the pyridine ring. The electron-withdrawing nature of the bromine atom influences nucleophilic attack sites, directing reactions toward specific positions on the ring. This selective reactivity is crucial for constructing complex molecules with precise three-dimensional shapes that optimize interactions with biological targets.

In conclusion, 2-Bromo-5-cyclopropylpyridine (CAS No. 1142197-14-5) is a versatile intermediate with broad applications in pharmaceutical and agrochemical research. Its unique structural features enable efficient synthesis of bioactive molecules, particularly kinase inhibitors targeting diseases such as cancer. As synthetic chemistry continues to evolve, this compound will remain a valuable tool for discovering new treatments and improving existing ones.

• 845973-17-3(Pyridine, 2-bromo-5-(2-phenylethyl)-)
• 144292-46-6(Pyridine, 2-bromo-5-nonyl-)
• 19842-08-1(2-Bromo-5-ethylpyridine)
• 1256788-23-4(2-Bromo-3-cyclopropylpyridine)
• 1142197-22-5(2-bromo-5-cyclopentylpyridine)
• 1142197-23-6(2-bromo-5-cyclohexylpyridine)
• 1142197-20-3(2-bromo-5-cyclobutylpyridine)
• 1142197-19-0(2-bromo-5-tert-butylpyridine)
• 1142197-16-7(2-Bromo-5-isopropylpyridine)
• 146203-98-7(Pyridine, 2-bromo-5-octyl-)