N-Chlorosuccinimide

N-Chlorosuccinimide^[1]
Names
	IUPAC name 1-chloropyrrolidine-2,5-dione
	Other names Chlorosuccinimide
Identifiers
CAS Number	128-09-6 ;
3D model (JSmol)	Interactive image;
Abbreviations	NCS
ChemSpider	29129 ;
ECHA InfoCard	100.004.436
EC Number	204-878-8;
PubChem CID	31398;
UNII	0FWP306H7X ;
CompTox Dashboard (EPA)	DTXSID2042199 ;
	InChI InChI=1S/C4H4ClNO2/c5-6-3(7)1-2-4(6)8/h1-2H2 Key: JRNVZBWKYDBUCA-UHFFFAOYSA-N ; InChI=1/C4H4ClNO2/c5-6-3(7)1-2-4(6)8/h1-2H2 Key: JRNVZBWKYDBUCA-UHFFFAOYAN;
	SMILES O=C1N(Cl)C(=O)CC1;
Properties
Chemical formula	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)
Related compounds
Related Imides	Succinimide ; N-Bromosuccinimide
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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

^ N-Chlorosuccinimide at Sigma-Aldrich
^ 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.
^ 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.
^ 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.
^ 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

[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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