''N''-Chlorosuccinimide

N-Chlorosuccinimide[1]
Skeletal formula of N-chlorosuccinimide
Space-filling model of the N-chlorosuccinimide molecule
Names
IUPAC name
1-chloropyrrolidine-2,5-dione
Other names
Chlorosuccinimide
Identifiers
3D model (JSmol)
Abbreviations NCS
ChemSpider
ECHA InfoCard 100.004.436
EC Number 204-878-8
UNII
Properties
C4H4ClNO2
Molar mass 133.53 g·mol−1
Appearance Solid
Density 1.65 g/cm3
Melting point 148 to 150 °C (298 to 302 °F; 421 to 423 K)
Hazards
Corrosive (C)
R-phrases (outdated) R22 R34
S-phrases (outdated) S26 S36/37/39 S45
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

N-Chlorosuccinimide is used for chlorinations[2] and as a mild oxidant.[3]

N-Iodosuccinimide (NIS), the iodine analog of N-chlorosuccinimide, and N-bromosuccinimide (NBS), the bromine analog, are used for similar applications.[4][5]

References

  1. ↑ N-Chlorosuccinimide at Sigma-Aldrich
  2. ↑ 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.
  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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