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109681

Sigma-Aldrich

N-Chlorosuccinimide

98%

Synonym(s):

1-Chloro-2,5-pyrrolidinedione, NCS

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R 539,00
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R 1 617,98

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100 G
R 539,00
500 G
R 1 617,98

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
form:
solid
Assay:
98%

R 539,00

List PriceR 550,00

Please contact Customer Service for Availability

Request a Bulk Order

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.[1]
It can be used for:
  • Conversion of diindenylzinc agent, [Zn(ind)2(pic)2]5 into 1-chloroindene.[1]
  • Selective cleavage of tryptophanyl peptide bonds.[2]
  • 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.[3]
  • Conversion of primary amides and aldoximes to their corresponding nitriles in the presence of triphenylphosphine.[4]
  • α-Chlorination of acyl-chlorides.[5]
  • Conversion of benzylic sulfides into α-chloro sulfides.[6]

Signal Word

Danger

Hazard 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. 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)
Chlorination of benzylic sulfides with N-chlorosuccinimide.
Tuleen D L and Marcum V C
The Journal of Organic Chemistry, 32(1), 204-206 (1967)
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)

Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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