N-CHLORO SUCCINIMIDE CAS No. 128-09-6
N-Chloro Succinimide (NCS) is a versatile and convenient reagent to chlorinate organic compounds by additions or electrophilic substitution.
Advantages over other reagents such as chlorine itself, chloramine T or sulfury chloride:
The ease of handling of the reagent itself
The mild reaction conditions of its use
The easy removal of Succinimide after the chlorination step.
1. Chlorination in carbonyl and carbonyl compounds :
Enolates and enol ethers of ketones and esters are chlorinated in the ά -position. With suitable chiral auxiliaries present, the reaction can proceed with high diasteroselectivity.
2. Chlorination of sulfides and sulfoxides:
NCS is the best reagent to transform sulfides into ά -Chloro sulfides, which are versatile intermediates, for example for the preparation of aldehydes and ketones. Variations of these reactions involve the degradation of carboxylic acids to ketones (via ά -sulfination, reaction with NCS and hydrolysis) and the removal of the 1, 3-dithiane protective group.
3. Research with vinylic and acetylenic compounds:
Organometallic derivatives of vinylic compounds are readily converted into the corresponding vinyl chlorides
4. Chlorinations of aromatic compounds:
Electron-rich heterocycles such as thiophenes, pyrroles and indoles can be chlorinated in the ά -position; the combination of NCS and dimehyl sulfide has been used to chlorinate phenols in ά -position.
: PE drums of 25kg & 40kg net
: not listed
: 5 - 121
: LD50 (rat, oral): 2700mg/kg
: R22, R36, R37, R38;
S22, S24, S25, S26