What is N-Chlorosuccinimide?

Identification

Name:    N-Chlorosuccinimide    

Synonyms:    1-Chloro-2,5-piperidinedione;Pyrrolidinedione, 1-chloro-;Succinic N-chloroimide;succinicn-chloroimide;Succinimide, N-chloro-;Succinochlorimide;N-Chlorosuccini1mide;N-ChlorosucciniMide, 98.5%    

CAS:    128-09-6    

Molecular Structure: 

MF:    C4H4ClNO2    

MW:    133.53    

EINECS:    204-878-8

Properties

Melting point     148-150 °C(lit.)   

Density     1,65 g/cm3    

Refractive index     1.4378 (estimate)    

Fp     >110°C    

Storage temp.     Store at +2°C to +8°C.    

Solubility     14g/l    

Pka    -2.78±0.20(Predicted)    

Form     Crystalline Powder    

Color     White    

N-chlorosuccinimide is a five-membered cyclic dicarboximide compound having a chloro substituent on the nitrogen atom. It is a pyrrolidinone and a dicarboximide. It derives from a succinimide. N-Chlorosuccinimide is the organic compound with the formula C2H4(CO)2NCl. A white solid, it is used for chlorinations. It is also used as a mild oxidant. NCS is related to succinimide, but with NCl in place of NH. The N-Cl bond is highly reactive, and NCS functions as a source of "Cl+".

Application

N-Chlorosuccinimide (NCS) is a chlorinating and oxidizing reagent. It is more efficient when compared to other chlorinating agents, such as 1,3-dichloro-5,5-dimethylhydantoin (NDDH) and trichloroisocyanuric acid (TCCA) due to its high regioselectivity.

It can be used for:

• Conversion of diindenylzinc agent, [Zn(ind)2(pic)2]5 into 1-chloroindene.

• Selective cleavage of tryptophanyl peptide bonds.

• Chemoselective oxidation of primary alcohols to aldehydes catalyzed by 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO) in the presence of tetrabutylammonium chloride under bi-phasic conditions.

• Conversion of primary amides and aldoximes to their corresponding nitriles in the presence of triphenylphosphine.

• α-Chlorination of acyl-chlorides.

• Conversion of benzylic sulfides into α-chloro sulfides.