MilliporeSigma
All Photos(3)

Documents

109681

Sigma-Aldrich

N-Chlorosuccinimide

98%

Sign Into View Organizational & Contract Pricing

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:
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

Looking for similar products? Visit Product Comparison Guide

Related Categories

Compare Similar Items

View Full Comparison

Show Differences

1 of 4

This Item
130672C813656480
vibrant-m

109681

N-Chlorosuccinimide

vibrant-m

130672

N-Hydroxysuccinimide

vibrant-m

C8136

Chloranilic acid

vibrant-m

56480

N-Hydroxysuccinimide

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

form

solid

form

solid

form

powder

form

solid

mp

148-150 °C (lit.)

mp

95-98 °C (lit.)

mp

≥300 °C (lit.)

mp

95-98 °C (lit.)

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


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Documents related to the products that you have purchased in the past have been gathered in the Document Library for your convenience.

Visit the Document Library

Difficulty Finding Your Product Or Lot/Batch Number?

Product numbers are combined with Pack Sizes/Quantity when displayed on the website (example: T1503-25G). Please make sure you enter ONLY the product number in the Product Number field (example: T1503).

Example:

T1503
Product Number
-
25G
Pack Size/Quantity

Additional examples:

705578-5MG-PW

PL860-CGA/SHF-1EA

MMYOMAG-74K-13

1000309185

enter as 1.000309185)

Having trouble? Feel free to contact Technical Service for assistance.

Lot and Batch Numbers can be found on a product's label following the words 'Lot' or 'Batch'.

Aldrich Products

  • For a lot number such as TO09019TO, enter it as 09019TO (without the first two letters 'TO').

  • For a lot number with a filling-code such as 05427ES-021, enter it as 05427ES (without the filling-code '-021').

  • For a lot number with a filling-code such as STBB0728K9, enter it as STBB0728 without the filling-code 'K9'.

Not Finding What You Are Looking For?

In some cases, a COA may not be available online. If your search was unable to find the COA you can request one.

Request COA

Customers Also Viewed

Slide 1 of 1

1 of 1

Succinimide for synthesis

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)
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)
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)
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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service