N-Chlorosuccinimide

N-Chlorosuccinimide (NCS) is the organic compound with the formula C₂H₄(CO)₂NCl. 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 (bleach), 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), and 1,3-dichloro-5,5-dimethylhydantoin.

Further reading

• N-chlorosuccinimide has been employed as chlorinating agent in combination with visible-light photoredox catalysts in organic synthesis.

References

External links

• N-Chlorosuccinimide at the Organic Chemistry Portal