<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-22 04:38:43 UTC</creation_date>
  <update_date>2026-08-22 16:42:25 UTC</update_date>
  <accession/>
  <common_name>N-Chlorosuccinimide</common_name>
  <class>SmallMolecule</class>
  <description>N-Chlorosuccinimide is an organic compound with the formula C4H4ClNO2 and an average molecular weight of 133.53 g/mol. N-Chlorosuccinimide belongs to the pyrrolidones, a subclass of pyrrolidines within the organic compounds.

This substance is found in or released from 18 recorded sources across several sectors. Within the category of electrical and electronic equipment, it is associated with antennas, amplifiers, communication cables or conductors, electric hearing aids, and auxiliary devices, among eight other sources. In the realm of food, food processing and cookware, it is linked to the preparation of vinegar and fermentation processes for beer. Additionally, it is found in building and construction materials, specifically roofs. Other recorded sources include credit card holders among household items and bleaching agents used in household cleaning and consumer products.</description>
  <categories/>
  <types/>
  <synonyms>
    <synonym>1-chloropyrrolidine-2,5-dione</synonym>
  </synonyms>
  <chemical_formula>C4H4ClNO2</chemical_formula>
  <average_molecular_weight>133.53</average_molecular_weight>
  <monisotopic_moleculate_weight>132.9930561</monisotopic_moleculate_weight>
  <iupac_name>1-chloropyrrolidine-2,5-dione</iupac_name>
  <traditional_iupac>chlorosuccinimide</traditional_iupac>
  <cas_registry_number>128-09-6</cas_registry_number>
  <smiles>ClN1C(=O)CCC1=O</smiles>
  <inchi>InChI=1S/C4H4ClNO2/c5-6-3(7)1-2-4(6)8/h1-2H2</inchi>
  <inchikey>JRNVZBWKYDBUCA-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pyrrolidines</class>
    <sub_class>Pyrrolidones</sub_class>
    <direct_parent>Pyrrolidine-2-ones</direct_parent>
    <alternate_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Dicarboximides</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>2-pyrrolidone</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboximide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Lactam</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>dicarboximide</descriptor>
      <descriptor>pyrrolidinone</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways/>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>-0.2</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.15</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.01</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.31e+02 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>18.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>1-chloropyrrolidine-2,5-dione</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>133.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>132.9930561</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>ClN1C(=O)CCC1=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H4ClNO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H4ClNO2/c5-6-3(7)1-2-4(6)8/h1-2H2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>JRNVZBWKYDBUCA-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>27.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>10.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <route_of_exposure/>
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  <lethaldose/>
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  <use_source/>
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  <symptoms/>
  <treatment/>
  <drugbank_id/>
  <hmdb_id/>
  <pubchem_compound_id>31398</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>29129</chemspider_id>
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</compound>
