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128-09-6 - N-Chlorosuccinimide, 98% - NCS - A10310 - Alfa Aesar

A10310 N-Chlorosuccinimide, 98%

CAS Number
128-09-6
Synonyms
NCS

Size Price ($) Quantity Availability
50g 13.41
250g 36.60
1000g 111.20
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N-Chlorosuccinimide, 98%

MDL
MFCD00005511
EINECS
204-878-8

Chemical Properties

Formula
C4H4ClNO2
Formula Weight
133.53
Melting point
146-150°
Density
1.65
Sensitivity
Moisture Sensitive
Solubility
Soluble in water, alcohol, benzene, acetone and acetic acid. Slightly soluble in ether, chloroform, carbon tetrachloride and petroleum ether.

Applications

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.

Notes

Light sensitive and moisture sensitive. Incompatible with strong oxidizing agents, strong acids, strong bases, amines, ammonia, iron and iron salts.

Literature 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).

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.

GHS Hazard and Precautionary Statements

Hazard Statements: H314-H318-H302

Causes severe skin burns and eye damage. Causes serious eye damage. Harmful if swallowed.

Precautionary Statements: P280-P305+P351+P338-P309-P310

Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF exposed or if you feel unwell: Immediately call a POISON CENTER or doctor/physician.

Other References

Merck
14,2164
Beilstein
113915
Hazard Class
8
Packing Group
II
Harmonized Tariff Code
2925.19
TSCA
Yes
RTECS
UY1013500

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