N-Chlorosuccinimide, 98%

Name: N-Chlorosuccinimide, 98%
SKU: A10310.30
Price: 57.00 USD

CAS: 128-09-6 | C4H4ClNO2 | 133.531 g/mol

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Catalog number A10310.30

also known as A10310-30

Price (USD)

57.00

Each

Quantity:

250 g

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Price (USD)

57.00

Each

Chemical Identifiers

CAS128-09-6

IUPAC Name1-chloropyrrolidine-2,5-dione

Molecular FormulaC4H4ClNO2

InChI KeyJRNVZBWKYDBUCA-UHFFFAOYSA-N

SMILESClN1C(=O)CCC1=O

Specifications

Specification Sheet

Assay from Supplier's CofA≥97.5% (Iodometric titration, US-sourced material)

Melting Point (clear melt)144-153?C

Solution TestColorless to pale yellow, clear or some fine fibres may be present: [5% in Acetone]

Assay (Iodometric Titration)≥97.5 to ≤102.5% (UK-sourced material)

CommentMaterial sourced in UK and US

Regioselective chlorination and oxidizing reagentN-Chlorosuccinimide is used as a chlorinating agent, mild oxidant and swimming pool disinfectant. It is used in the microdetermination of hydrazine salts by titrimetry as well as in the detection of arsenic in the +3 oxidative state. It is also employed in the production of rubber additives. Further, it is used as pharmaceutical intermediate and antibiotic drugs intermediate.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications
Regioselective chlorination and oxidizing reagentN-Chlorosuccinimide is used as a chlorinating agent, mild oxidant and swimming pool disinfectant. It is used in the microdetermination of hydrazine salts by titrimetry as well as in the detection of arsenic in the +3 oxidative state. It is also employed in the production of rubber additives. Further, it is used as pharmaceutical intermediate and antibiotic drugs intermediate.

Solubility
Soluble in water, alcohol, benzene, acetone and acetic acid. Slightly soluble in ether, chloroform, carbon tetrachloride and petroleum ether.

Notes
Light sensitive and moisture sensitive. Incompatible with strong oxidizing agents, strong acids, strong bases, amines, ammonia, iron and iron salts.

RUO – Research Use Only

General References:

Source of positive chlorine in chlorination and oxidation reactions.
Methyl ketones may be monochlorinated via their Li enolates: J. Org. Chem., 49, 1286 (1984). For the ɑ-chlorination of acid chlorides formed in situ, see: Tetrahedron Lett., 3235 (1974). For chlorination of deactivated anilines, see: Synthesis, 669 (1985).
In the presence of triphenylphosphine or triphenyl phosphite, converts alcohols to alkyl chlorides stereospecifically with inversion: Tetrahedron Lett., 3937 (1973). For a review, see: Org. React., 29, 1 (1983). Amides have been prepared by treatment of a carboxylic acid with NCS/PPh₃ followed by an amine: Synth. Commun., 25, 959 (1995).
With dimethyl sulfide, forms the Corey-Kim reagent, a mild, selective oxidant for alcohols. For a review, see: Synthesis, 857 (1990); for tabulated examples, see: Org. Synth. Coll., 6, 220 (1988).
Primary alcohols are oxidized cleanly to aldehydes using NCS and a catalytic amount of TEMPO, A12733 under phase-transfer conditions: J. Org. Chem., 61, 7452 (1996).
NCS in ether is a convenient alternative to hypochlorite for the conversion of amines to N-chloroamines, for use, e.g. in the Hofmann-Loeffler reaction, see: Chem. Ber., 88, 883 (1955).
Yu, J.; Shin, G. A.; Oh, B. S.; Kye, J. I.; Yoon, J. N-chlorosuccinimide as a novel agent for biofouling control in the polyamide reverse osmosis membrane process. Desalination 2015, 357, 1-7.
Ravi, C.; Chandra Mohan, D.; Adimurthy, S. N-Chlorosuccinimide-Promoted Regioselective Sulfenylation of Imidazoheterocycles at Room Temperature. Org. Lett. 2014, 16 (11), 2978-2981.