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109681

Sigma-Aldrich

N-Chlorosuccinimide

98%

Sinónimos:

1-Chloro-2,5-pyrrolidinedione, NCS

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About This Item

Fórmula empírica (notación de Hill):
C4H4ClNO2
Número de CAS:
128-09-6
Peso molecular:
133.53
Beilstein/REAXYS Number:
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.)

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

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Sigma-Aldrich

8.07971

Succinimide

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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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)
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