700-16-3 | Pentafluoropyridine

CAS:700-16-3 | Pentafluoropyridine ,Description

Pentafluoropyridine, also known as 2,2,2-trifluoro-1-pyridinamine, is an organic compound with the chemical formula C5H3F5N. It is a colorless liquid that is miscible with most organic solvents. It is used as a reagent in organic synthesis, and as a ligand in coordination chemistry. It is also used as a catalyst for a variety of reactions such as the Wittig reaction, the Stille reaction, and the Suzuki-Miyaura reaction.
 

Scientific Research Applications

• Synthesis of Heterocycles and Macrocycles: Pentafluoropyridine is used as a building block for synthesizing poly-substituted pyridine and macrocyclic derivatives, with potential applications in life science and supramolecular fields (Sandford, 2006).
• Deoxyfluorination of Carboxylic Acids: It facilitates the deoxyfluorination of carboxylic acids to acyl fluorides, and is used in one-pot amide bond formation, providing a pathway to synthesize amides (Brittain & Cobb, 2021).
• Preparation of Poly-Substituted Pyridines: Pentafluoropyridine serves as a starting material for preparing a range of pyridine derivatives with different substituents (Benmansour, Chambers, Hoskin, & Sandford, 2001).
• Reactivity with Group 14 Elements: Its interaction with group 14 elements (Si, Ge, Sn) shows diverse reactivity, leading to various chemical processes and products (Samuel et al., 2013).
• Hydrodefluorination at Rhodium: Pentafluoropyridine is involved in hydrodefluorination reactions with rhodium, used for catalytic C-F activation processes (Braun, Noveski, Ahijado, & Wehmeier, 2007).
• Catalytic Hydrodefluorination by Cluster Hydrides: It undergoes catalytic hydrodefluorination in the presence of cluster hydrides containing phosphines, demonstrating regioselective reactions (Beltrán, Feliz, Llusar, Mata, & Safont, 2011) .
• Ultrasound Promoted Synthesis: Pentafluoropyridine reacts with nucleophiles under ultrasonic irradiation, forming derivatives at room temperature, offering a novel synthesis method (Ranjbar‐Karimi, Mashak-Shoshtari, & Darehkordi, 2011) .
• Modification of Peptide Systems: It has been used to modify peptide systems, enhancing their proteolytic stability in pharmaceutical applications (Gimenez, Mooney, Dose, Sandford, Coxon, & Cobb, 2017).

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