N-Chlorosuccinimide

Synonym(s):1-Chloro-2,5-pyrrolidinedione;N-Chlorosuccinimide;NCS;NCS, Succinchlorimide

CAS NO.：128-09-6
Empirical Formula: C4H4ClNO2
Molecular Weight: 133.53
MDL number: MFCD00005511
EINECS: 204-878-8
SAFETY DATA SHEET (SDS)
Update Date: 2024-05-16 14:11:51

What is N-Chlorosuccinimide?

Description

N-Chlorosuccinimide (NCS) is generally used for chlorination reactions or certain mild oxidations (ex. Corey-Kim oxidation). NCS is a solid which makes is a useful alternative to gaseous chlorine for certain reactions.

The Uses of N-Chlorosuccinimide

N-Chlorosuccinimide is a chlorinating agent for the side-chain halogenation of alkylarenes. It is used frequently for the side-chain chlorination of sensitive hetarenes.

The Uses of N-Chlorosuccinimide

N-Chlorosuccinimide
To a solution of the SM (0.10 g, 0.23 mmol) in anhydrous DMF (2.3 mL) was added NCS (0.038 g, 0.29 mmol) at RT. The reaction mixture was stirred at RT for 16 h. The excess solvent was removed in vacuo, and the obtained residue was diluted with ice-H2O, then extracted with EtOAc (3 x 20 mL). The combined organics were washed with brine (25 mL), dried (Na2SO4), and concentrated. The residue was purified by Prep TLC (10% MeOH/DCM) to provide the product as a yellow solid. [0.037 g, 35%]

What are the applications of Application

N-Chlorosuccinimide is A regioselective chlorination and oxidizing reagent

Properties of N-Chlorosuccinimide

Melting point:	148-150 °C (lit.)
Density	1,65 g/cm³
Flash point:	>110°C
storage temp.	Store at +2°C to +8°C.
solubility	14g/l
form	Crystalline Powder
color	White
Water Solubility	Soluble in water, alcohol, benzene, acetone and acetic acid. Slightly soluble in ether, chloroform, carbon tetrachloride and petroleum ether.
Sensitive	Moisture Sensitive
Boiling point:	216.5°C

Safety information for N-Chlorosuccinimide

Signal word	Danger
Pictogram(s)	Corrosion Corrosives GHS05 Exclamation Mark Irritant GHS07 Environment GHS09
GHS Hazard Statements	H290:Corrosive to Metals H302:Acute toxicity,oral H314:Skin corrosion/irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation H410:Hazardous to the aquatic environment, long-term hazard
Precautionary Statement Codes	P260:Do not breathe dust/fume/gas/mist/vapours/spray. P273:Avoid release to the environment. P280:Wear protective gloves/protective clothing/eye protection/face protection. P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.