N -chlorosuccinimide

Structural formula
General
Surname	N -chlorosuccinimide
other names	NCS; Succinic chloride; 1-chloropyrrolidine-2,5-dione;
Molecular formula	C 4 H 4 ClNO 2
Brief description	colorless solid with a smell of chlorine
External identifiers / databases
EC number	204-878-8
ECHA InfoCard	100.004.436
PubChem	31398
Wikidata	Q286192
properties
Molar mass	133.53 g mol −1
Physical state	firmly
density	1.65 g cm −3
Melting point	148-151 ° C
boiling point	216.5 ° C
solubility	14 g l −1 in water (20 ° C)
safety instructions
H and P phrases	H: 302-314
	P: 280-305 + 351 + 338-310
Thermodynamic properties
ΔH f 0	−357.9 kJ / mol
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

N -chlorosuccinimide , usually referred to as NCS for short, is the nitrogen- chlorinated imide of succinic acid .

Extraction and presentation

NCS can be made by treating succinimide with elemental chlorine .

properties

The heat of decomposition determined by DSC is −215 kJ · mol ⁻¹ or −1610 kJ · kg ⁻¹ .

use

On a laboratory scale, NCS is mainly used as a chlorinating agent, for example in the chlorination of alkenes in the allyl position or of alkyl aromatics in the benzyl position . It is used in larger quantities in the production of active pharmaceutical ingredients (especially antibiotics ). Compared to elemental chlorine (a caustic, poisonous gas), NCS is easier to store, handle and dose. When NCS is converted, the water-soluble succinimide is formed as a by-product .

The use of N -chlorosuccinimide as a chlorinating agent is an example of a synthesis method which proceeds with low atom economy .

Individual evidence

↑ ^a ^b ^c ^d ^e data sheet N-chlorosuccinimide (PDF) from Merck , accessed on February 28, 2010.
↑ ^a ^b Data sheet N-Chlorosuccinimide from Sigma-Aldrich , accessed on April 12, 2011 ( PDF ).
↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Standard Thermodynamic Properties of Chemical Substances, pp. 5-25.
↑ Grewer, T .; Klais, O .: Exothermic decomposition - investigations of the characteristic material properties , VDI-Verlag, series "Humanisierung des Arbeitsleben", Volume 84, Düsseldorf 1988, ISBN 3-18-400855-X , p. 10.

[Merck-1] ↑ ^a ^b ^c ^d ^e data sheet N-chlorosuccinimide (PDF) from Merck , accessed on February 28, 2010.

[Sigma-2] Data sheet N-Chlorosuccinimide from Sigma-Aldrich , accessed on April 12, 2011 ( PDF ).

[CRC90_5_25-3] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Standard Thermodynamic Properties of Chemical Substances, pp. 5-25.

[Grewer-4] Grewer, T .; Klais, O .: Exothermic decomposition - investigations of the characteristic material properties , VDI-Verlag, series "Humanisierung des Arbeitsleben", Volume 84, Düsseldorf 1988, ISBN 3-18-400855-X , p. 10.