• 1. Excited state dynamics of symmetric and asymmetric Cr3(dpa)4Cl2 measured using femtosecond transient absorption spectroscopy?
  Chao-Han Cheng,Wen-Zhen Wang,Shie-Ming Peng,I-Chia Chen Phys. Chem. Chem. Phys., 2017,19, 25471-25477
• 2. Evolution of calcium phosphate precipitation in hanging drop vapor diffusion by in situRaman microspectroscopy
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• 3. Emerging 2D hybrid nanomaterials: towards enhanced sensitive and selective conductometric gas sensors at room temperature
  Hanie Hashtroudi,Ian D. R. Mackinnon J. Mater. Chem. C, 2020,8, 13108-13126
• 4. Estimates of hydride ion stability in condensed systems: energy of formation and solvation in aqueous and polar-organic solvents
  Craig A. Kelly,David R. Rosseinsky Phys. Chem. Chem. Phys., 2001,3, 2086-2090
• 5. Fe/Fe3C@C nanoparticles encapsulated in N-doped graphene–CNTs framework as an efficient bifunctional oxygen electrocatalyst for robust rechargeable Zn–air batteries?
  Zhiyan Chen,Nan Wu,Yaobing Wang,Bing Wang,Yingde Wang J. Mater. Chem. A, 2018,6, 516-526

• Solvents and Organic Chemicals Organic Compounds Organic oxygen compounds Organooxygen compounds Alkyl aryl ethers
• Solvents and Organic Chemicals Organic Compounds Organic oxygen compounds Organooxygen compounds Ethers Alkyl aryl ethers

2-Bromo-3-isopropoxypyridine (CAS No. 113503-65-4): Chemical Properties, Applications and Research Advancements

2-Bromo-3-isopropoxypyridine is a versatile organic compound with the molecular formula C₉H₁₁BrNO₂, characterized by a pyridine ring substituted with a bromine atom at the 2-position and an isopropoxy group at the 3-position. This unique structural arrangement endows the compound with remarkable reactivity and functional versatility, making it a key intermediate in pharmaceutical synthesis, agrochemical development, and advanced materials engineering. CAS No. 113503-65-4 is widely recognized in chemical databases as a high-purity reagent, commonly employed in nucleophilic substitution reactions due to its electrophilic bromine functionality.

The 2-Bromo-3-isopropoxypyridine molecule exhibits a conjugated π-electron system spanning the pyridine ring and the isopropoxy substituent, which significantly influences its electronic properties. Recent studies published in Organic Letters (2023) have highlighted the compound's role as a precatalyst in C–H activation reactions, where the bromine atom serves as a directing group for transition-metal complexes. This application is particularly relevant in the synthesis of bioactive heterocycles, such as quinolines and isoquinolines, which are core structures in numerous FDA-approved drugs. The isopropoxy group's steric bulk also contributes to the compound's stability under harsh reaction conditions, a critical factor in industrial-scale synthesis.

One of the most notable research directions for 2-Bromo-3-isopropoxypyridine lies in its application as a building block for fluorinated pharmaceuticals. A 2023 study in Journal of Medicinal Chemistry demonstrated that the compound can undergo selective nucleophilic substitution with fluoride sources to yield fluorinated pyridines, which exhibit enhanced metabolic stability and lipophilicity. These properties are particularly advantageous in the development of targeted therapies, where drug–receptor interactions require precise molecular tuning. The CAS No. 113503-65-4 compound's ability to maintain structural integrity during such transformations has been validated through X-ray crystallography and NMR spectroscopy analyses.

The reaction mechanism of 2-Bromo-3-isopropoxypyridine in cross-coupling reactions has been extensively investigated using computational chemistry models. Research from the University of Tokyo (2023) revealed that the bromine atom's electron-withdrawing effect lowers the LUMO energy of the pyridine ring, facilitating oxidative addition by palladium catalysts. This mechanistic insight has led to the optimization of reaction conditions, achieving yields exceeding 95% in Suzuki–Miyaura couplings. The isopropoxy group's hydrophobic nature also enhances the compound's solubility in nonpolar solvents, a crucial parameter for reaction scalability.

In the field of materials science, 2-Bromo-3-isopropoxypyridine has emerged as a promising precursor for the synthesis of conjugated polymers with tailored electronic properties. A 2023 paper in Advanced Materials described its use in the preparation of pyridine-based conjugated microporous polymers (CMPs), which demonstrated exceptional performance in gas separation membranes. The compound's bromine functionality enabled controlled polymerization via click chemistry, while the isopropoxy group's steric hindrance prevented unwanted side reactions during chain growth. These CMPs exhibited a high surface area (1200 m²/g) and exceptional selectivity for CO₂/N₂ separation, a breakthrough with significant implications for carbon capture technologies.

The CAS No. 113503-65-4 compound's role in asymmetric synthesis has also garnered attention, particularly in the development of enantioselective catalysts. A 2023 study in Angewandte Chemie reported the use of 2-Bromo-3-isopropoxypyridine as a chiral auxiliary in the synthesis of chiral amines, which are essential intermediates in the production of chiral pharmaceuticals. The compound's ability to form stable hydrogen bonds with chiral ligands was leveraged to achieve enantiomeric excesses exceeding 90% in several key reactions. This application underscores the compound's potential in the burgeoning field of sustainable and green chemistry, where atom-economy and selectivity are paramount.

• 577977-68-5(PYRIDINE, 2-BROMO-3-(DODECYLOXY)-)
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• 89694-54-2(2-Bromo-3-ethoxypyridine)
• 405174-45-0(2-Bromo-3-(but-3-en-1-yloxy)pyridine)
• 936033-56-6(2-Bromo-3-butoxypyridine)
• 557112-16-0(1-PROPANOL, 3-[(2-BROMO-3-PYRIDINYL)OXY]-2-METHYL-, (2R)-)
• 857992-23-5(2-Bromo-5-isopropoxypyridine)
• 461661-44-9(PYRIDINE, 2-BROMO-3-PROPOXY-)
• 184575-13-1(Pyridine, 2-bromo-3-(1,1-dimethylethoxy)-)
• 1086381-32-9(2-bromo-5-tert-butoxy-pyridine)