109681
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:
Molecular Weight:
133.53
NACRES:
NA.22
PubChem Substance ID:
eCl@ss:
39151413
UNSPSC Code:
12352101
EC Number:
204-878-8
MDL number:
Beilstein/REAXYS Number:
113915
Assay:
98%
Form:
solid
Quality Level
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
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:
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.
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signalword
Danger
hcodes
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
8A - Combustible corrosive hazardous materials
wgk
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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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)
Selective chemical cleavage of tryptophanyl peptide bonds by oxidative chlorination with N-chlorosuccinimide.
Shechter Y, et al.
Biochemistry, 15(23), 5071-5075 (1976)
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