N-Chlorosuccinimide

N-Chlorosuccinimide^[1]
Names
	Preferred IUPAC name 1-Chloropyrrolidine-2,5-dione
	Other names Chlorosuccinimide
Identifiers
CAS Number	128-09-6 ;
3D model (JSmol)	Interactive image;
Abbreviations	NCS
Beilstein Reference	113915
ChEBI	CHEBI:53203;
ChEMBL	ChEMBL2107513;
ChemSpider	29129 ;
ECHA InfoCard	100.004.436
EC Number	204-878-8;
Gmelin Reference	122816
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	white solid
Density	1.65 g/cm3
Melting point	148 to 150 °C (298 to 302 °F; 421 to 423 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H314, H319, H335, H412
Precautionary statements	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). verify (what is ?) Infobox references

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⁺".

^ N-Chlorosuccinimide at Sigma-Aldrich
^ Golebiewski, W. Marek; Gucma, Miro slaw (2007). "Applications of N-chlorosuccinimide in organic synthesis". Synthesis (23): 3599–3619. doi:10.1055/s-2007-990871.
^ 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.

[1] N-Chlorosuccinimide at Sigma-Aldrich

[sym-2] Golebiewski, W. Marek; Gucma, Miro slaw (2007). "Applications of N-chlorosuccinimide in organic synthesis". Synthesis (23): 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.

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N-Chlorosuccinimide

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