N-Chlorosuccinimide

N-Chlorosuccinimide ("NCS")is the organic compound with the formula C2H4(CO)2NCl. A white solid, it 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+".

N-Chlorosuccinimide[1]
Skeletal formula of N-chlorosuccinimide
Space-filling model of the N-chlorosuccinimide molecule
Names
Preferred IUPAC name
1-Chloropyrrolidine-2,5-dione
Other names
Chlorosuccinimide
Identifiers
3D model (JSmol)
Abbreviations NCS
113915
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.436
EC Number
  • 204-878-8
122816
UNII
  • InChI=1S/C4H4ClNO2/c5-6-3(7)1-2-4(6)8/h1-2H2 ☒N
    Key: JRNVZBWKYDBUCA-UHFFFAOYSA-N ☒N
  • InChI=1/C4H4ClNO2/c5-6-3(7)1-2-4(6)8/h1-2H2
    Key: JRNVZBWKYDBUCA-UHFFFAOYAN
  • O=C1N(Cl)C(=O)CC1
Properties
C4H4ClNO2
Molar mass 133.53 g·mol−1
Appearance white solid
Density 1.65 g/cm3
Melting point 148 to 150 °C (298 to 302 °F; 421 to 423 K)
Hazards
GHS labelling:
GHS05: CorrosiveGHS07: Exclamation mark
Danger
H302, H314, H319, H335, H412
P260, P261, P264, P270, P271, P273, P280, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P330, P337+P313, P363, P403+P233, P405, P501
Related compounds
Related Imides
 Succinimide
N-Bromosuccinimide
N-Iodosuccinimide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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.[2]

Electron-rich arenes are readily monochlorinated by NCS. Aniline and mesitylene are converted to the respective chlorinated derivatives.[2]

Further reading
  • Delaney, Paul A.; R. Johnstone (1985). "Solvent effects in the chlorination of tetrahydrothiophens with N-chlorosuccinimide". Tetrahedron. 41 (18): 3845–3851. doi:10.1016/S0040-4020(01)91405-X.

References
  1. N-Chlorosuccinimide at Sigma-Aldrich
  2. Golebiewski, W. Marek; Gucma, Miro slaw (2007). "Applications of N-chlorosuccinimide in organic synthesis". Synthesis: 3599–3619. doi:10.1055/s-2007-990871.
  3. Kim, Kwan Soo; I. Cho; B. Yoo; Y. Song; C. Hahn (1984). "Selective oxidation of primary and secondary alcohols using di-isopropyl sulphide–N-chlorosuccinimide". J. Chem. Soc., Chem. Commun. (12): 762–763. doi:10.1039/C39840000762.
  4. Beebe, T. R.; R. L. Adkins; C. C. Bogardus; B. Champney; P. S. Hii; P. Reinking; J. Shadday; W. D. Weatherford; M. W. Webb; S. W. Yates (1983). "Primary alcohol oxidation with N-iodosuccinimide". J. Org. Chem. 48 (18): 3126–3128. doi:10.1021/jo00166a046.
  5. Castanet, Anne-Sophie; F. Colobert; P. Broutin (2002). "Mild and regioselective iodination of electron-rich aromatics with N-iodosuccinimide and catalytic trifluoroacetic acid". Tetrahedron Lett. 43 (29): 5047–5048. doi:10.1016/S0040-4039(02)01010-9.
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