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
Beilstein:
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.)
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:
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
Precautionary Statements
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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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)
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)
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