109681

N-Chlorsuccinimid

98%

• Synonym(e): 1-Chloro-2,5-pyrrolidinedione, NCS
• Empirische Formel (Hill-System): C₄H₄ClNO₂
• CAS-Nummer: 128-09-6
• Molekulargewicht: 133.53
• Beilstein: 113915
• EG-Nummer: 204-878-8
• MDL-Nummer: MFCD00005511
• UNSPSC-Code: 12352101
• eCl@ss: 39151413
• PubChem Substanz-ID: 24846932
• NACRES: NA.22

Eigenschaften

• Qualitätsniveau: 200
• Assay: 98%
• Form: solid
• mp (Schmelzpunkt): 148-150 °C (lit.)
• SMILES String: ClN1C(=O)CCC1=O
• InChI: 1S/C4H4ClNO2/c5-6-3(7)1-2-4(6)8/h1-2H2
• InChIKey: JRNVZBWKYDBUCA-UHFFFAOYSA-N

Beschreibung

Anwendung

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.

Sicherheitshinweise

• Piktogramme: GHS05,GHS07,GHS09
• Signalwort: Danger
• H-Sätze: H290,H302,H314,H335,H410
• P-Sätze: P260 - P273 - P280 - P301 + P312 - P303 + P361 + P353 - P305 + P351 + P338
• Gefahreneinstufungen: Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1 - Met. Corr. 1 - Skin Corr. 1B - STOT SE 3
• Zielorgane: Respiratory system
• Lagerklassenschlüssel: 8A - Combustible corrosive hazardous materials
• WGK: WGK 2
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable
• Persönliche Schutzausrüstung: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges