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Regioselective chlorination and oxidizing reagentN-Chlorosuccinimide is used as a chlorinating agent, mild oxidant and swimming pool disinfectant. It is used in the microdetermination of hydrazine salts by titrimetry as well as in the detection of arsenic in the +3 oxidative state. It is also employed in the production of rubber additives. Further, it is used as pharmaceutical intermediate and antibiotic drugs intermediate.
Source of positive chlorine in chlorination and oxidation reactions.
Methyl ketones may be monochlorinated via their Li enolates: J. Org. Chem., 49, 1286 (1984). For the ɑ-chlorination of acid chlorides formed in situ, see: Tetrahedron Lett., 3235 (1974). For chlorination of deactivated anilines, see: Synthesis, 669 (1985).
In the presence of triphenylphosphine or triphenyl phosphite, converts alcohols to alkyl chlorides stereospecifically with inversion: Tetrahedron Lett., 3937 (1973). For a review, see: Org. React., 29, 1 (1983). Amides have been prepared by treatment of a carboxylic acid with NCS/PPh3 followed by an amine: Synth. Commun., 25, 959 (1995).
With dimethyl sulfide, forms the Corey-Kim reagent, a mild, selective oxidant for alcohols. For a review, see: Synthesis, 857 (1990); for tabulated examples, see: Org. Synth. Coll., 6, 220 (1988).
Primary alcohols are oxidized cleanly to aldehydes using NCS and a catalytic amount of TEMPO, A12733 under phase-transfer conditions: J. Org. Chem., 61, 7452 (1996).
NCS in ether is a convenient alternative to hypochlorite for the conversion of amines to N-chloroamines, for use, e.g. in the Hofmann-Loeffler reaction, see: Chem. Ber., 88, 883 (1955).
Yu, J.; Shin, G. A.; Oh, B. S.; Kye, J. I.; Yoon, J. N-chlorosuccinimide as a novel agent for biofouling control in the polyamide reverse osmosis membrane process. Desalination 2015, 357, 1-7.
Ravi, C.; Chandra Mohan, D.; Adimurthy, S. N-Chlorosuccinimide-Promoted Regioselective Sulfenylation of Imidazoheterocycles at Room Temperature. Org. Lett. 2014, 16 (11), 2978-2981.
Mentions de danger (UE): H302-H314-H318
Harmful if swallowed. Causes severe skin burns and eye damage. Causes serious eye damage.
Mentions de prudence: P260-P201-P280-P304+P340-P405-P501a
Do not breathe dust/fume/gas/mist/vapours/spray. Obtain special instructions before use. Wear protective gloves/protective clothing/eye protection/face protection. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.