N-Chlorosuccinimide

N-Chlorosuccinimide ("NCS")is the organic compound with the formula C2H4(CO)2NCl. A white solid, it 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 Cl+ sources, such as bleach (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 (NIS), the iodine analog of N-chlorosuccinimide.
 * N-bromosuccinimide (NBS), the bromine analog of N-chlorosuccinimide.
 * Other N-chloro compounds that are commercially available include chloramine-T, trichloroisocyanuric acid ((OCNCl)3), 1,3-dichloro-5,5-dimethylhydantoin.