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: 2024-08-24 19:19:26

What is N-Chlorosuccinimide?

Description

N-chlorosuccinimide is a five-membered cyclic dicarboximide compound having a chloro substituent on the nitrogen atom. It is a pyrrolidinone and a dicarboximide. It is functionally related to a succinimide. It is generally used for chlorination reactions or mild oxidations (ex. Corey-Kim oxidation). NCS is a solid, which makes it a valuable alternative to gaseous chlorine for certain reactions.

Chemical properties

white crystalline powder

The Uses of N-Chlorosuccinimide

N-Chlorosuccinimide is a reagent useful for allylic and benzylic chlorination, while at the same time, avoiding the electrophilic addition of chlorine to a pi bond. The reaction mechanism involves a free radical pathway and usually requires a radical chain initiator such as a peroxide. As 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 (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.
N-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.

What are the applications of Application

N-Chlorosuccinimide is A regioselective chlorination and oxidizing reagent

Definition

ChEBI: N-chlorosuccinimide is a five-membered cyclic dicarboximide compound having a chloro substituent on the nitrogen atom. It is a pyrrolidinone and a dicarboximide. It derives from a succinimide.

Flammability and Explosibility

Non flammable

Properties of N-Chlorosuccinimide

Melting point:	148-150 °C (lit.)
Density	1,65 g/cm³
vapor pressure	1.04Pa at 25℃
refractive index	1.4378 (estimate)
Flash point:	>110°C
storage temp.	Store at +2°C to +8°C.
solubility	14g/l
form	Crystalline Powder
pka	-2.78±0.20(Predicted)
color	White
Odor	chlorine odor
Water Solubility	Soluble in water, alcohol, benzene, acetone and acetic acid. Slightly soluble in ether, chloroform, carbon tetrachloride and petroleum ether.
Sensitive	Moisture Sensitive
Merck	14,2164
BRN	113915
Boiling point:	216.5°C
CAS DataBase Reference	128-09-6(CAS DataBase Reference)
NIST Chemistry Reference	N-Chlorosuccinimide(128-09-6)
EPA Substance Registry System	N-Chlorosuccinimide (128-09-6)

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.