N-Chlorosuccinimide (NCS)

Introduction

N-Chlorosuccinimide (NCS) is a very powerful chlorinating reagent, which also finds applications as mild oxidizing agent. This colourless, commercially available, inexpensive solid is thermally stable to some extent. It is least toxic as well as highly selective compared to chlorinating agents, such as 1,3-dichloro-5,5-dimethylhydan­toin (NDDH) and trichloroisocyanuric acid (TCCA). In the last two decades, it has emerged as a useful mediator or catalyst for many chemical reactions, such as functional groups replacement, halocyclization, formation of ­heterocyclic systems, carbon-carbon bond formation, rearrangement, deprotections, and functional group transformations. [¹] NCS also possess some bactereostatic and anti-bactericidal activity as it forms hypochlorous acid upon slow hydrolysis with water. [²] NCS is soluble in carbon tetrachloride at room temperature while its conjugate product succinimide is not, which leads to easy separation from the reaction mixture.

References

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