1-chloropyrrolidine-2,5-dione

• ChemBase ID: 74324
• Molecular Formular: C4H4ClNO2
• Molecular Mass: 133.53306
• Monoisotopic Mass: 132.99305605
• SMILES: N1(C(=O)CCC1=O)Cl
• Canonical SMILES: ClN1C(=O)CCC1=O
• InChI: InChI=1S/C4H4ClNO2/c5-6-3(7)1-2-4(6)8/h1-2H2
• InChIKey: JRNVZBWKYDBUCA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-chloropyrrolidine-2,5-dione
• IUPAC Traditional name: chlorosuccinimide
• Synonyms: 1-chloropyrrolidine-2,5-dione; NCS; 1-Chloropyrrolidine-2,5-dione; N-Chlorosuccinimide 99%; N-CHLOROSUCCINIMIDE; Chlorosuccinimide; N-Chlorosuccinimide; N-氯丁二酰亚胺; N-氯代丁二酰亚胺

Database IDs

• CAS Number: 128-09-6
• EC Number: 204-878-8
• MDL Number: MFCD00005511
• Beilstein Number: 113915
• Merck Index: 142164
• PubChem SID: 162039243; 24846932
• PubChem CID: 31398
• Chemspider ID: 29129
• Unique Ingredient Identifier: 0FWP306H7X
• Wikipedia Title: N-Chlorosuccinimide

CALCULATED PROPERTIES

• Acid pKa: 18.07768
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -0.23125698
• LogD (pH = 7.4): -0.23125698
• Log P: -0.23125698
• Molar Refractivity: 27.6177 cm^3
• Polarizability: 10.710621 Å^3
• Polar Surface Area: 37.38 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Solid
• Melting Point: 144-148°C; 146-150°C; 148 - 150°C; 148-150 °C; 148-150 °C(lit.)
• Flash Point: >110°C
• Density: 1.65

Safety Information

• Storage Condition: Room Temperature (15-30°C), Desiccate, Protect from light
• Storage Warning: Corrosive/Harmful/Light Sensitive/Moisture Sensitive; Moisture Sensitive
• RTECS: UY1013500
• European Hazard Symbols: Corrosive (C); X
• UN Number: 3261; UN3261
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; II
• Risk Statements: 22-34; R22 R34
• Safety Statements: 26-36/37/39-45; S26 S36/37/39 S45
• TSCA Listed: 是
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H314; H314-H318-H302
• GHS Precautionary statements: P280-P305 + P351 + P338-P310; P280-P305+P351+P338-P309-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3261 8/PG 2

Product Information

• Purity: ≥96.0% (RT); 95+%; 98%
• Grade: purum
• Empirical Formula (Hill Notation): C4H4ClNO2

DETAILS

MP Biomedicals - 02150658

Crystalline

MP Biomedicals - 05212213

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 109681

Application
Regioselective chlorination and oxidizing reagent.
Packaging
100, 500 g in poly bottle

Sigma Aldrich - 26370

Other Notes
Versatile chlorinating and oxidizing agent; antibacterial 2; 1

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).