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N-Chlorosuccinimide structure
N-Chlorosuccinimide structure


Iupac Name:1-chloropyrrolidine-2,5-dione
CAS No.: 128-09-6
Molecular Weight:133.53300
Modify Date.: 2022-11-09 11:06
Introduction: Chlorinating agent. View more+
1. Names and Identifiers
1.1 Name
1.2 Synonyms

1-Chloro-2,5-piperidinedione 1-Chloro-2,5-pyrrolidinedione 1-chloropyrrolidine-2,5-dione 2,5-Pyrrolidinedione, 1-chloro- Chlorosuccinimide EINECS 204-878-8 MFCD00005511 N-chlorobutanimide N-Chlorosuccini1mide Pyrrolidinedione, 1-chloro- Succinic N-chloroimide succinicn-chloroimide Succinimide, N-chloro- Succinimide, N-chloro- (8CI) Succinochlorimide

1.3 CAS No.
1.4 CID
1.6 Molecular Formula
C4H4ClNO2 (isomer)
1.7 Inchi
1.8 InChkey
1.9 Canonical Smiles
1.10 Isomers Smiles
2. Properties
2.1 Density
1,65 g/cm3
2.1 Melting point
2.1 Boiling point
200.5ºC at 760 mmHg
2.1 Refractive index
2.1 Flash Point
2.1 Precise Quality
2.1 PSA
2.1 logP
2.1 Solubility
2.2 Appearance
White Crystalline Powder
2.3 Storage
Moisture Sensitive. Store under Nitrogen. Ambient temperatures.
2.4 Chemical Properties
white crystalline powder
2.5 Color/Form
Orthorhombic crystals
White crystalline powder
2.6 Decomposition
When heated to decomposition it emits toxic fumes of /hydrogen chloride;/ and nitroxides.
2.7 Odor
Odor of chlorine
2.8 PH
Acid to litmus (1:50 aq soln)
2.9 pKa
2.10 Water Solubility
Slightly soluble
2.11 Spectral Properties
IR: 4273 (Coblentz Society Spectral Collection)
NMR: 6226 (Sadtler Research Laboratories Spectral Collection)
MASS: 4080 (National Bureau of Standards EPA-NIH Mass Spectra Data Base, NSRDS-NBS-63)
2.12 Stability
Stable at room temperature in closed containers under normal storage and handling conditions.
2.13 StorageTemp
Store at +2°C to +8°C.
3. Use and Manufacturing
3.1 Definition
ChEBI: A five-membered cyclic dicarboximide compound having a chloro substituent on the nitrogen atom. N-Chlorosuccinimide Preparation Products And Raw materials Preparation Products
3.2 GHS Classification
Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 85 companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria by 5 of 85 companies. For more detailed information, please visit ECHA C&L website

Of the 11 notification(s) provided by 80 of 85 companies with hazard statement code(s):

H302 (98.75%): Harmful if swallowed [Warning Acute toxicity, oral]
H314 (55%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
H319 (41.25%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H335 (41.25%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
H412 (38.75%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P260, P261, P264, P270, P271, P273, P280, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P330, P337+P313, P363, P403+P233, P405, and P501
3.3 Methods of Manufacturing
... from succinimide.
3.4 Usage
Chlorinating agent.
4. Safety and Handling
4.1 Symbol
GHS05, GHS07
4.1 Hazard Codes
4.1 Signal Word
4.1 Risk Statements
R22; R34
4.1 Safety Statements
4.1 Packing Group
4.1 Hazard Class
4.1 Hazard Declaration
4.1 DisposalMethods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
UN 3261 8/PG 2
4.2 FirePotential
Stored as a dust it heats spontaneously.
4.3 Caution Statement
P280-P305 + P351 + P338-P310
4.3 WGK Germany
4.3 Protective Equipment and Clothing
4.4 Reactivities and Incompatibilities
Explosive reaction with aliphatic alcohols, benzylamine, or hydrazine hydrate.
4.5 Report

EPA Genetic Toxicology Program.

4.6 Skin, Eye, and Respiratory Irritations
4.7 Safety

Hazard Codes:?CorrosiveC,IrritantXi
Risk Statements: 22-34?
R22:Harmful if swallowed.?
R34:Causes burns.
Safety Statements: 26-36/37/39-45-37/39?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.?
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)?
S37/39:Wear suitable gloves and eye/face protection.

4.8 Sensitive
Moisture Sensitive
4.9 Specification

?N-Chlorosuccinimide (CAS NO.128-09-6) is a white crystal, soluble in water and alcohols, it can be used as pharmaceutical intermediates, organic synthesis chlorinating agent, it can also be used to prepare rubber additives, synthesis as chlorinating agent, antibiotic drugs intermediates.

?Production method is through the ammoniated acid chloride derived. Through dropping ammonia,react with succinic acid , stirring heated at 102°C steam to get rid of water. Vacuum distillation, collecting 180°C after the distillate to get succinimide. Molten succinimide increased to acetic acid aqueous solution, stirring cooled to 0-5°C, dropping sodium hypochlorite, control reaction in the 8°C below (otherwise there is risk of explosion). To clarify the reaction solution that is reached when the end point, centrifugation, filter cake and washing to neutral, drying, drying to get.

4.10 Toxicity
1. ???

orl-rat LDLo:1000?mg/kg

??? PHRPA6 ?? Public Health Reports. 59 (1944),541.
2. ???

ivn-rat LDLo:200?mg/kg

??? PHRPA6 ?? Public Health Reports. 59 (1944),541.

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Skin corrosion, Category 1B

2.2 GHS label elements, including precautionary statements

Signal word


Hazard statement(s)

H302 Harmful if swallowed

H314 Causes severe skin burns and eye damage

Precautionary statement(s)

P264 Wash ... thoroughly after handling.

P270 Do not eat, drink or smoke when using this product.

P260 Do not breathe dust/fume/gas/mist/vapours/spray.

P280 Wear protective gloves/protective clothing/eye protection/face protection.


P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell.

P330 Rinse mouth.

P301+P330+P331 IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.

P303+P361+P353 IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water [or shower].

P363 Wash contaminated clothing before reuse.

P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing.

P310 Immediately call a POISON CENTER/doctor/\u2026

P321 Specific treatment (see ... on this label).

P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.


P405 Store locked up.


P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification


9. Other Information
9.0 Usage
Regioselective chlorination and oxidizing reagentN-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.
9.1 Merck
9.2 BRN
9.3 Chemical Properties
white crystalline powder
9.4 Uses
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.
9.5 Uses
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.
9.6 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.
10. Computational chemical data
  • Molecular Weight: 133.53300g/mol
  • Molecular Formula: C4H4ClNO2
  • Compound Is Canonicalized: True
  • XLogP3-AA: -0.2
  • Exact Mass: 132.9930561
  • Monoisotopic Mass: 132.9930561
  • Complexity: 129
  • Rotatable Bond Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Topological Polar Surface Area: 37.4
  • Heavy Atom Count: 8
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
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