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109681

Sigma-Aldrich

N-Chlorosuccinimide

98%

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Synonym(s):
1-Chloro-2,5-pyrrolidinedione, NCS
Empirical Formula (Hill Notation):
C4H4ClNO2
CAS Number:
Molecular Weight:
133.53
Beilstein/REAXYS Number:
113915
EC Number:
MDL number:
UNSPSC Code:
12352101
eCl@ss:
39151413
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

98%

form

solid

mp

148-150 °C (lit.)

SMILES string

ClN1C(=O)CCC1=O

InChI

1S/C4H4ClNO2/c5-6-3(7)1-2-4(6)8/h1-2H2

InChI key

JRNVZBWKYDBUCA-UHFFFAOYSA-N

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Application

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.

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1 - Met. Corr. 1 - Skin Corr. 1B - STOT SE 3

target_organs

Respiratory system

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges


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A rapid and facile conversion of primary amides and aldoximes to nitriles and ketoximes to amides with triphenylphosphine and N-chlorosuccinimide.
Iranpoor N, et al.
Synthetic Communications, 32(16), 2535-2541 (2002)
Chlorination of benzylic sulfides with N-chlorosuccinimide.
Tuleen D L and Marcum V C
The Journal of Organic Chemistry, 32(1), 204-206 (1967)
Fabio Vivarelli et al.
Scientific reports, 9(1), 11636-11636 (2019-08-14)
A large number of basic researches and observational studies suggested the cancer preventive activity of vitamin E, but large-scale human intervention trials have yielded disappointing results and actually showed a higher incidence of prostate cancer although the mechanisms underlying the
Efficient and highly selective oxidation of primary alcohols to aldehydes by N-chlorosuccinimide mediated by oxoammonium salts.
Einhorn J, et al.
The Journal of Organic Chemistry, 61(21), 7452-7454 (1996)
Gaelle Picarda et al.
Journal of virology, 93(16) (2019-05-31)
Cytomegalovirus (CMV) establishes a lifelong infection facilitated, in part, by circumventing immune defenses mediated by tumor necrosis factor (TNF)-family cytokines. An example of this is the mouse CMV (MCMV) m166 protein, which restricts expression of the TNF-related apoptosis-inducing ligand (TRAIL)

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