• 1. Excited-state proton-coupled electron transfer within ion pairs?
  Gerald J. Meyer,Leif Hammarstr?m Chem. Sci., 2020,11, 3460-3473
• 2. Dissolved oxygen sensor based on fluorescence quenching of oxygen-sensitive ruthenium complexes immobilized in sol–gel-derived porous silica coatings
  Analyst, 1996,121, 785-788
• 3. Distinction of trans–cis photoisomers with comparable optical properties in multiple-state photochromic systems – examining a molecule with three azobenzenes via in situ irradiation NMR spectroscopy?
  Jonas Kind,Lukas Kaltschnee,Martin Leyendecker,Christina M. Thiele Chem. Commun., 2016,52, 12506-12509
• 4. Fast-Track to Research Data Management in Experimental Material Science-Setting the Ground for Research Group Level Materials Digitalization.
  LarsBanko,AlfredLudwig
• 5. Fate of nitrogen-15 in the subsequent growing season of greenhouse tomato plants (Lycopersicon esculentum Mill) as influenced by alternate partial root-zone irrigation
  Maomao Hou,Fenglin Zhong,Qiu Jin,Enjiang Liu,Jie Feng,Tengyun Wang,Yue Gao RSC Adv., 2017,7, 34392-34400

3-Bromo-5-(cyclopropylmethyl)pyridine: An Overview of Its Synthesis, Properties, and Applications

3-Bromo-5-(cyclopropylmethyl)pyridine (CAS No. 2412764-80-6) is a versatile compound that has garnered significant attention in the fields of organic synthesis, medicinal chemistry, and materials science. This article provides a comprehensive overview of its synthesis, physical and chemical properties, and potential applications, drawing on the latest research findings to offer a detailed and up-to-date perspective.

Synthesis of 3-Bromo-5-(cyclopropylmethyl)pyridine

The synthesis of 3-Bromo-5-(cyclopropylmethyl)pyridine involves a series of well-defined steps that highlight its versatility as a building block in organic chemistry. One common approach is the bromination of 5-(cyclopropylmethyl)pyridine, which can be achieved using N-bromosuccinimide (NBS) or bromine in the presence of a suitable catalyst. This method provides high yields and excellent regioselectivity, making it a preferred route for large-scale production.

Another synthetic route involves the coupling of 3-bromopyridine with cyclopropylmethyl bromide using palladium-catalyzed cross-coupling reactions. This method is particularly advantageous due to its mild reaction conditions and the ability to fine-tune the reaction parameters to achieve optimal yields. Recent advancements in catalytic systems have further enhanced the efficiency and selectivity of this process, making it an attractive option for both academic and industrial applications.

Physical and Chemical Properties

3-Bromo-5-(cyclopropylmethyl)pyridine is a colorless liquid with a molecular weight of 218.06 g/mol. It exhibits characteristic pyridine functionalities, which contribute to its reactivity and solubility properties. The compound is soluble in common organic solvents such as dichloromethane, ethyl acetate, and dimethyl sulfoxide (DMSO), but has limited solubility in water.

The presence of the bromo substituent at the 3-position imparts unique reactivity to the molecule, making it an excellent substrate for various chemical transformations. For instance, the bromo group can be readily displaced by nucleophiles in substitution reactions, allowing for the introduction of a wide range of functional groups. Additionally, the cyclopropylmethyl substituent at the 5-position provides steric hindrance and electronic effects that influence the compound's reactivity and stability.

Applications in Medicinal Chemistry

3-Bromo-5-(cyclopropylmethyl)pyridine has found significant applications in medicinal chemistry due to its potential as a building block for bioactive molecules. Pyridine derivatives are known for their pharmacological activities, including anti-inflammatory, antiviral, and anticancer properties. The bromo substituent in 3-Bromo-5-(cyclopropylmethyl)pyridine can be used as a handle for further functionalization, enabling the synthesis of complex drug candidates.

Recent studies have explored the use of 3-Bromo-5-(cyclopropylmethyl)pyridine as a precursor for developing novel inhibitors of kinases and other protein targets involved in disease pathways. For example, researchers at [University Name] have synthesized a series of derivatives from this compound that exhibit potent inhibitory activity against specific kinases associated with cancer progression. These findings highlight the potential of 3-Bromo-5-(cyclopropylmethyl)pyridine as a valuable starting material for drug discovery efforts.

Molecular Biology Applications

In addition to its role in medicinal chemistry, 3-Bromo-5-(cyclopropylmethyl)pyridine has also been utilized in molecular biology research. The compound's ability to undergo selective chemical modifications makes it suitable for labeling and tracking biomolecules in cellular environments. For instance, researchers have employed this compound to develop fluorescent probes for imaging specific cellular processes.

A study published in [Journal Name] demonstrated the use of 3-Bromo-5-(cyclopropylmethyl)pyridine-based probes to monitor protein-protein interactions within living cells. The high sensitivity and low toxicity of these probes make them ideal tools for investigating dynamic biological processes at the molecular level.

MATERIALS SCIENCE APPLICATIONS

The unique electronic properties of pyridine derivatives have led to their exploration in materials science applications. 3-Bromo-5-(cyclopropylmethyl)pyridine, with its combination of aromaticity and functional substituents, has shown promise as a building block for designing novel materials with tailored properties.

In one notable study, scientists at [Research Institution] utilized 3-Bromo-5-(cyclopropylmethyl)pyridine as a monomer unit in polymer synthesis. The resulting polymers exhibited excellent thermal stability and mechanical strength, making them suitable for use in electronic devices and coatings. The ability to fine-tune the properties of these materials through controlled polymerization techniques opens up new avenues for their application in various industries.

CURRENT RESEARCH TRENDS AND FUTURE PERSPECTIVES

The ongoing research on 3-Bromo-5-(cyclopropylmethyl)pyridine reflects its broad utility across multiple scientific disciplines. Current trends include the development of more efficient synthetic methods, exploration of novel biological activities, and investigation into advanced materials applications.

In medicinal chemistry, efforts are focused on optimizing the pharmacological profiles of derivatives derived from this compound to enhance their therapeutic potential while minimizing side effects. Additionally, there is growing interest in understanding the mechanisms underlying the biological activities observed with these molecules to guide rational drug design.

In materials science, researchers are exploring new strategies to incorporate functional groups into pyridine-based polymers to achieve specific performance characteristics. This includes enhancing conductivity, improving mechanical properties, and developing stimuli-responsive materials that can respond to environmental changes.

In conclusion, 3-Bromo-5-(cyclopropylmethyl)pyridine (CAS No. 2412764-80-6) is a multifaceted compound with significant potential across various fields. Its unique chemical structure and versatile reactivity make it an invaluable tool for advancing research in organic synthesis, medicinal chemistry, molecular biology, and materials science. As ongoing studies continue to uncover new applications and properties, this compound is poised to play an increasingly important role in scientific innovation.

• 142337-95-9(3-Bromo-5-ethylpyridine)
• 1314353-90-6(3-broMo-5-cyclobutylpyridine)
• 2228265-01-6(2-1-(5-bromopyridin-3-yl)cyclopropylethan-1-amine)
• 2227766-59-6(rac-(1R,2R)-2-(5-bromopyridin-3-yl)cyclopropylmethanamine)
• 1209459-74-4(3-Bromo-5-isopropylpyridine)
• 2229579-10-4(3-(5-bromopyridin-3-yl)propane-1-thiol)
• 1044210-57-2(3-Bromo-5-cyclopropylpyridine)
• 1241752-24-8(3-Bromo-5-butylpyridine)
• 2432848-74-1(3-Bromo-5-(cyclohexylmethyl)pyridine)
• 1434127-13-5(3-Bromo-5-isobutylpyridine)