Authors: Reza Ranjbar-Karimi, Alireza Poorfreidoni

Perhalopyridines: Synthesis and Synthetic Utility

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ISBN: 978-981-14-7377-7 (Print)
ISBN: 978-981-14-7379-1 (Online)
Year of Publication: 2020
DOI: 10.2174/97898114737911200101
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Halogenated pyridines can be used as interesting starting materials in a wide range of organic synthesis methods. Substituted pyridine compounds are used generally as starting materials in the nucleophilic substitution reactions and have unique scaffolds for the construction of other heterocyclic and macrocyclic compounds. They also have important medicinal properties. Due to synthetic difficulties in the synthesis of the highly substituted pyridine derivatives from pyridine itself, perhalopyridines have a special importance in this regard. This book covers the synthetic reactions and applications of perhalopyridines. An introductory chapter introduces the reader to the physical and chemical properties of halopyridines, followed by 3 chapters which focus on pentafluoropyridine, pentachloropyridine and pentabromopyridine, respectively. The focused chapters provide information about synthetic methods and relevant nucleophilic reactions for each of the listed perhalopyridines and their derivatives. The book is a quick reference on perhalopyridines for students of applied chemistry, organic chemistry and chemical engineering.


The heterocyclic ring is found in half of known compounds and most of these compounds have possessed an aromatic heterocyclic ring. Heteroaromatic compounds were found in a great number of metabolism products, pest-controlling agents, dyeing agents, flavors and commercial synthetic compounds such as drugs. Heterocyclic systems have broad applications especially in pharmaceutical chemistry and this accelerated the discovery and development of the chemistry of heterocycles. Heteroaromatic compounds have broad chemistry and numerous investigations have been carried out for synthetic methods of heteroaromatic derivatives to continuous development and applications of these systems. Perhalogenated pyridines are an attractive group of heteroaromatics that play an important role in organic chemistry, biochemistry, and pharmaceutical chemistry. These compounds have great interesting chemistry because of their reactivity toward nucleophilic attack. Therefore, they have become unique scaffolds for the construction of other heterocyclic and macrocyclic compounds. So far, there has been extensive research on perhalopyridine compounds. Some of the books published in the heterocyclic chemistry area have been cited for the synthesis, their reactions and their applications. For example, in “Fluorinated heterocyclic compounds: synthesis, chemistry, and applications” (Edited by Petrov, Viacheslav A. 2009), a brief summary of perfluoropyridine has been gathered or in “Pyridine and Its Derivatives” (Edited by R. A. Abramovitch 2009), some aspect about pentafluoro- and pentachloropyridine are briefly mentioned. Recently, we published a review article concerning “Utility of pentachloropyridine in organic synthesis” in the journal of the Iranian chemical society. In this book, we tried to focus on perhalopyridine including perfluoropyridine, perchloropyridine, perbromopyridine, so that readers can easily get to know the chemistry of these compounds. I would like to thank my coworker, Dr. Alireza Poorfreidoni, who helped me complete this book. I wish to thank those that reviewed the book and provided helpful suggestions. Finally, I have to thank my wife, Fatemeh SayyedBagheri, and my children, Javad, Mohadeseh, Ali, and Zahra, for putting up with me during manuscript preparation. I would also like to thank Bentham Science for the opportunity to publish this book. I have no conflicts of interest in relation to this book.


Not applicable.


The authors declare no conflict of interest, financial or otherwise.


Declared none.

Reza Ranjbar-Karimi
Department of Chemistry, Faculty of Science
Vali-e-Asr University of Rafsanjan
Islamic Republic of Iran


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