N-Chlorosuccinimide TCI C0291

Chemical Identity

Other names: NCS
CAS No.: 128-09-6
PubChem: CID 31398·SID 87565445
Formula: C4H4ClNO2
Molecular weight: 133.53 g/mol
Purity: >98.0%(T)
Reference databases: ChEBI·ChemSpider·ECHA·Wikipedia

Full identifiers (IUPAC, SMILES, InChIKey)

IUPAC: 1-chloropyrrolidine-2,5-dione
SMILES: C1CC(=O)N(C1=O)Cl
InChIKey: JRNVZBWKYDBUCA-UHFFFAOYSA-N
MDL: MDL00005511

Rp 477.750,00

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TCI C0291 N-Chlorosuccinimide (NCS, CAS 128-09-6) is a classic solid source of electrophilic chlorine that is far easier to weigh and handle than chlorine gas. It is routinely used for allylic and benzylic chlorination, alpha-chlorination of carbonyl compounds, and selective chlorination of electron-rich aromatics. NCS also drives controlled oxidations of alcohols to aldehydes and ketones, most notably in the Corey–Kim protocol with dimethyl sulfide. AMI Scientific supplies this TCI reagent in 25 g, 100 g, and 500 g packs; as an oxidising and corrosive solid, it should be kept cool, dry, and well away from reducing agents and combustible materials.

Advantages (TCI brochure)

Reacts with B2240 to generate the active oxidant in situ

TCI brochures (PDF)

Organocatalyst for Electrophilic Halogenation of Aromatic Compounds under Mild Conditions 2022-05-17 · p. 1
High-Performance Chlorinating Agents and Brominating Agent for Regioselective Halogenation of (Hetero)arenes 2025-03-13 · p. 1
Halogenation Reagents 2026-04-03 · p. 6
Oxidizing Agents 2025-06-11 · p. 3

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From the TCI brochure

Mukaiyama oxidation of alcohols

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Chauhan (2010). N-Chlorosuccinimide (NCS). Synlett doi:10.1055/s-0029-1219581
Dim et al. (2024). Ka-Band Rotational Spectroscopy of Succinimide and N-Chlorosuccinimide. The Journal of Physical Chemistry A doi:10.1021/acs.jpca.4c06004
(2006). N-Chlorosuccinimide. Cold Spring Harbor Protocols doi:10.1101/pdb.caut256

References were compiled automatically from Crossref and every DOI was verified to exist. AMI Scientific is not affiliated with the authors or the publishers.