N-Chlorosuccinimide

N-Chlorosuccinimide is the organic compound with the formula C₂H₄₂NCl. This white solid is used for chlorinations. It is also used as a mild oxidant. NCS is related to succinimide, but with N-Cl in place of N-H. The N–Cl bond is highly reactive, and NCS functions as a source of "Cl⁺".

Synthesis and selected reactions

NCS is produced from succinimide by treatment with sources, such as sodium hypochlorite, and t-butylhypochlorite, and even chlorine.
Electron-rich arenes are readily monochlorinated by NCS. Aniline and mesitylene are converted to the respective chlorinated derivatives.

Related reagents

N-Iodosuccinimide, the iodine analog of N-chlorosuccinimide.
N-bromosuccinimide, the bromine analog of N-chlorosuccinimide.
Other N-chloro compounds that are commercially available include chloramine-T, trichloroisocyanuric acid, 1,3-dichloro-5,5-dimethylhydantoin.