Production Method 1

946002-10-4

Reaction Conditions

Reference

Preparation of aryl, heteroaryl, aryloxy and heteroaryloxy tropolone derivatives and tautomers for iron regulation in animals useful for treating a disease or condition associated with iron dysregulation or dysfunctional iron homeostasis

, World Intellectual Property Organization, , ,

Production Method 2

946002-10-4

Reaction Conditions

Reference

Design, synthesis and biological evaluation of 7H-pyrrolo[2,3-d]pyrimidin-4-amine derivatives as selective Btk inhibitors with improved pharmacokinetic properties for the treatment of rheumatoid arthritis

He, Linhong; Pei, Heying; Zhang, Chufeng; Shao, Mingfeng; Li, Dan; et al, European Journal of Medicinal Chemistry, 2018, 145, 96-112

(5-fluoropyridin-2-yl)boronic acid Preparation Products

• (5-fluoropyridin-2-yl)boronic acid (946002-10-4)

• 1. Estimation of activation energy for electroporation and pore growth rate in liquid crystalline and gel phases of lipid bilayers using molecular dynamics simulations?
  Amit Kumar Majhi,Subbarao Kanchi,V. Venkataraman,K. G. Ayappa,Prabal K. Maiti Soft Matter, 2015,11, 8632-8640
• 2. Excellent peroxidase mimicking property of CuO/Pt nanocomposites and their application as an ascorbic acid sensor?
  Xinhuan Wang,Shuangfei Cai,Cui Qi Analyst, 2017,142, 2500-2506
• 3. Esterase-responsive polymeric prodrug-based tumor targeting nanoparticles for improved anti-tumor performance against colon cancer?
  Gang Pan,Yi-jie Bao,Jie Xu,Tao Liu,Cheng Liu,Yan-yan Qiu,Xiao-jing Shi,Hui Yu,Ting-ting Jia,Xia Yuan,Ze-ting Yuan,Yi-jun Cao RSC Adv., 2016,6, 42109-42119
• 4. Enabling shape memory and healable effects in a conjugated polymer by incorporating siloxane via dynamic imine bond?
  Yaling Zhang,Chunhui Dai,Shiwei Zhou,Bin Liu Chem. Commun., 2018,54, 10092-10095
• 5. Evolution in surface coverage of CH3NH3PbI3?XClXvia heat assisted solvent vapour treatment and their effects on photovoltaic performance of devices
  Dhirendra K. Chaudhary,Pramendra Kumar,Lokendra Kumar RSC Adv., 2016,6, 94731-94738

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyridines and derivatives Pyridines and derivatives
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyridines and derivatives

(5-Fluoropyridin-2-yl)boronic acid (CAS No. 946002-10-4): An Overview of Its Synthesis, Applications, and Recent Research Advances

(5-Fluoropyridin-2-yl)boronic acid (CAS No. 946002-10-4) is a versatile organic compound that has garnered significant attention in the fields of organic synthesis, medicinal chemistry, and materials science. This compound, also known as 5-fluoro-2-pyridylboronic acid, is characterized by its unique structure, which combines a pyridine ring with a boronic acid functional group. The presence of the fluorine atom further enhances its reactivity and utility in various chemical transformations.

The synthesis of (5-fluoropyridin-2-yl)boronic acid typically involves the reaction of 5-fluoro-2-chloropyridine with borane or boronic acid derivatives. One common method involves the palladium-catalyzed borylation of 5-fluoro-2-chloropyridine using bis(pinacolato)diboron as the boron source. This reaction is highly efficient and provides the desired product in good yields. The resulting (5-fluoropyridin-2-yl)boronic acid can be further purified by recrystallization or column chromatography.

In medicinal chemistry, (5-fluoropyridin-2-yl)boronic acid has found applications as a key intermediate in the synthesis of various bioactive molecules. The pyridine ring and the boronic acid group provide multiple points of functionalization, making it an attractive building block for the development of new drugs. For instance, recent studies have shown that derivatives of (5-fluoropyridin-2-yl)boronic acid can be used to target specific enzymes or receptors involved in various diseases, including cancer and neurodegenerative disorders.

One notable application of (5-fluoropyridin-2-yl)boronic acid is in the field of Suzuki-Miyaura coupling reactions. This palladium-catalyzed cross-coupling reaction is widely used in organic synthesis to form carbon-carbon bonds between aryl or vinyl halides and aryl or vinyl boronic acids. The presence of the fluorine atom in (5-fluoropyridin-2-yl)boronic acid can significantly influence the reactivity and selectivity of these coupling reactions, making it a valuable reagent for the synthesis of complex molecules with specific electronic properties.

Recent research has also explored the use of (5-fluoropyridin-2-yl)boronic acid in materials science. For example, it has been used to synthesize novel polymers with unique optical and electronic properties. These polymers have potential applications in organic electronics, such as organic light-emitting diodes (OLEDs) and organic photovoltaic cells (OPVs). The ability to fine-tune the properties of these materials through the incorporation of fluorinated pyridine units makes (5-fluoropyridin-2-yl)boronic acid an important precursor in this field.

In addition to its synthetic utility, (5-fluoropyridin-2-yl)boronic acid has been studied for its biological activities. Research has shown that certain derivatives of this compound exhibit potent antiviral and antibacterial properties. For instance, a study published in the Journal of Medicinal Chemistry reported that a series of 5-fluoro-pyridine-based compounds demonstrated significant inhibitory effects against several strains of bacteria and viruses. These findings highlight the potential of (5-fluoropyridin-2-yl)boronic acid as a lead compound for the development of new therapeutic agents.

The environmental impact of chemical compounds is an important consideration in their development and application. Studies on the biodegradability and toxicity of (5-fluoropyridin-2-yl)boronic acid have shown that it exhibits low toxicity and good biodegradability under controlled conditions. This makes it a more environmentally friendly option compared to some other boronic acids used in similar applications.

In conclusion, (5-fluoropyridin-2-yl)boronic acid (CAS No. 946002-10-4) is a multifaceted compound with a wide range of applications in organic synthesis, medicinal chemistry, materials science, and environmental studies. Its unique structure and reactivity make it an invaluable reagent for researchers working on the development of new materials and drugs. As research continues to advance, it is likely that new applications for this compound will be discovered, further expanding its utility in various scientific fields.

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