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109681

Sigma-Aldrich

N-Chlorosuccinimide

98%

Synonym(s):

1-Chloro-2,5-pyrrolidinedione, NCS

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About This Item

Empirical Formula (Hill Notation):
C4H4ClNO2
CAS Number:
128-09-6
Molecular Weight:
133.53
Beilstein:
113915
EC Number:
204-878-8
MDL number:
MFCD00005511
UNSPSC Code:
12352101
eCl@ss:
39151413
PubChem Substance ID:
24846932
NACRES:
NA.22

Assay

98%

form

solid

mp

148-150 °C (lit.)

functional group

imide

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.

Signal Word

Danger

Hazard Statements

H290,H302,H314,H335,H410

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

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
STBL4352
0000232590
0000220885
STBL2773
STBL0569

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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)
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)
Chlorination of benzylic sulfides with N-chlorosuccinimide.
Tuleen D L and Marcum V C
The Journal of Organic Chemistry, 32(1), 204-206 (1967)
Selective chemical cleavage of tryptophanyl peptide bonds by oxidative chlorination with N-chlorosuccinimide.
Shechter Y, et al.
Biochemistry, 15(23), 5071-5075 (1976)
Efficient. alpha.-halogenation of acyl chlorides by N-bromosuccinimide, N-chlorosuccinimide, and molecular iodine.
Harpp D N, et al.
The Journal of Organic Chemistry, 40(23), 3420-3427 (1975)
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