N-Chlorosuccinimide

N-Chlorosuccinimide[1]
IUPAC name 1-chloropyrrolidine-2,5-dione
Other names Chlorosuccinimide
Identifiers
Abbreviations	NCS
CAS number	128-09-6 Y
PubChem	31398
UNII	0FWP306H7X Y
EC number	204-878-8
Jmol-3D images	Image 1
SMILES C1CC(=O)N(C1=O)Cl
InChI InChI=InChI=1/C4H4ClNO2/c5-6-3(7)1-2-4(6)8/h1-2H2
Properties
Molecular formula	C4H4ClNO2
Molar mass	133.53 g mol−1
Appearance	Solid
Melting point	148-150 °C, 421-423 K, 298-302 °F
Hazards
EU classification	Corrosive (C)
R-phrases	R22 R34
S-phrases	S26 S36/37/39 S45
Related compounds
Related Imides	Succinimide N-Bromosuccinimide
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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 and 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, and 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. 

External links

• N-Chlorosuccinimide and N-Iodosuccinimide at Organic Chemistry Portal