N-Chlorosuccinimide
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| Abbreviations | NCS |
| Template:Longitem | 113915 |
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| EC Number | Template:Unbulleted list |
| Template:Longitem | 122816 |
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| Template:Longitem | Template:Chembox Elements/molecular formula |
| Molar mass | Template:Chem molar mass |
| Appearance | white solid |
| Density | 1.65 g/cm3 |
| Melting point | Template:Chembox CalcTemperatures |
| Template:Longitem | Succinimide N-Bromosuccinimide N-Iodosuccinimide |
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N-Chlorosuccinimide (NCS) is the organic compound with the formula C2H4(CO)2NCl. This white solid is used for chlorinations.[2] It is also used as a mild oxidant.[3] 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 Template:Chem2 sources, such as sodium hypochlorite (bleach), and t-butylhypochlorite, and even chlorine.[2]
Electron-rich arenes are readily monochlorinated by NCS. Aniline and mesitylene are converted to the respective chlorinated derivatives.[2]
Related reagents
- N-Iodosuccinimide (NIS), the iodine analog of N-chlorosuccinimide.[4]
- N-bromosuccinimide (NBS), the bromine analog of N-chlorosuccinimide.[5]
- Other N-chloro compounds that are commercially available include chloramine-T, trichloroisocyanuric acid ((OCNCl)3), 1,3-dichloro-5,5-dimethylhydantoin.[2]
Further reading
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- N-chlorosuccinimide has been employed as chlorinating agent in combination with visible-light photoredox catalysts in organic synthesis.[6]
References
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