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.