N-Chlorosuccinimide

• Catalog No.: A10310
• CAS Number: 128-09-6
• M. F.: C4H4ClNO2
• M. W.: 133.53306
• Purity: 98%

SYNONYMS

• Title: N-氯丁二酰亚胺
• IUPAC name: 1-chloropyrrolidine-2,5-dione
• IUPAC Traditional name: chlorosuccinimide
• Synonyms: NCS

DATABASE IDS

• Merck Index: 142164
• EC Number: 204-878-8
• Beilstein Number: 113915
• MDL Number: MFCD00005511
• CAS Number: 128-09-6

PROPERTIES

• Purity: 98%
• Density: 1.65
• Melting Point: 146-150°C
• GHS Hazard statements: H314-H318-H302
• European Hazard Symbols: X
• European Hazard Symbols: Corrosive (C)
• GHS Precautionary statements: P280-P305+P351+P338-P309-P310
• Risk Statements: 22-34
• RTECS: UY1013500
• Safety Statements: 26-36/37/39-45
• Storage Warning: Moisture Sensitive
• TSCA Listed: 是
• Hazard Class: 8
• UN Number: UN3261
• Packing Group: II

REFERENCES

• 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).