<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:10:14 UTC</creation_date>
  <update_date>2025-11-18 23:37:43 UTC</update_date>
  <accession>FDB012543</accession>
  <name>(Chloromethyl)oxirane</name>
  <description>It is used for cross-linking dextrose units in food starch.</description>
  <synonyms>
    <synonym>(+/-)-2-(Chloromethyl)oxirane</synonym>
    <synonym>(+/-)-epichlorohydrin</synonym>
    <synonym>(chloromethyl)-oxirane</synonym>
    <synonym>(chloromethyl)ethylene oxide</synonym>
    <synonym>(DL)-&amp;alpha;-epichlorohydrin</synonym>
    <synonym>(DL)-alpha-Epichlorohydrin</synonym>
    <synonym>(RS)-3-Chloro-1,2-epoxypropane</synonym>
    <synonym>&amp;alpha;-epichlorohydrin</synonym>
    <synonym>1-Chloro-2,3-epoxy propone</synonym>
    <synonym>1-chloro-2,3-Epoxy-propane</synonym>
    <synonym>1-Chloro-2,3-epoxypropane</synonym>
    <synonym>1,2-Epoxy-3-chloropropane</synonym>
    <synonym>2-(Chloromethyl)-oxirane</synonym>
    <synonym>2-(Chloromethyl)oxirane</synonym>
    <synonym>2,3-Epoxypropyl chloride</synonym>
    <synonym>3-Chloro-1,2-epoxypropane</synonym>
    <synonym>3-Chloro-1,2-propylene oxide</synonym>
    <synonym>3-Chloro-propylene oxide</synonym>
    <synonym>3-Chloropropene-1,2-oxide</synonym>
    <synonym>3-Chloropropyl epoxide</synonym>
    <synonym>3-Chloropropylene oxide</synonym>
    <synonym>a-Epichlorohydrin</synonym>
    <synonym>Allyl chloride oxide</synonym>
    <synonym>Alpha-epichlorohydrin</synonym>
    <synonym>Chloro-1,2-epoxypropane</synonym>
    <synonym>Chloro-1,2-propylene oxide</synonym>
    <synonym>Chloro-2,3-epoxypropane</synonym>
    <synonym>Chloromethyloxirane</synonym>
    <synonym>Chloropropene-1,2-oxide</synonym>
    <synonym>Chloropropyl epoxide</synonym>
    <synonym>Chloropropylene</synonym>
    <synonym>Chloropropylene oxide</synonym>
    <synonym>DL-a-epichlorohydrin</synonym>
    <synonym>Epi-chlorohydrin</synonym>
    <synonym>Epichloorhydrine</synonym>
    <synonym>Epichlorhydrin</synonym>
    <synonym>Epichlorhydrine</synonym>
    <synonym>Epichlorohydrin</synonym>
    <synonym>Epichlorophydrin</synonym>
    <synonym>Epoxy-3-chloropropane</synonym>
    <synonym>Epoxypropyl chloride</synonym>
    <synonym>Gamma-chloropropylene oxide</synonym>
    <synonym>Glycerol epichlorhydrin</synonym>
    <synonym>Glycerol epichlorohydrin</synonym>
    <synonym>Glycidyl chloride</synonym>
    <synonym>Oxirane, (chloromethyl)-</synonym>
    <synonym>Oxirane, 2-(chloromethyl)-</synonym>
    <synonym>Propane, 1-chloro-2,3-epoxy-</synonym>
  </synonyms>
  <chemical_formula>C3H5ClO</chemical_formula>
  <average_molecular_weight>92.524</average_molecular_weight>
  <monisotopic_moleculate_weight>92.002892489</monisotopic_moleculate_weight>
  <iupac_name>2-(chloromethyl)oxirane</iupac_name>
  <traditional_iupac>epichlorohydrin</traditional_iupac>
  <cas_registry_number>106-89-8</cas_registry_number>
  <smiles>ClCC1CO1</smiles>
  <inchi>InChI=1S/C3H5ClO/c4-1-3-2-5-3/h3H,1-2H2</inchi>
  <inchikey>BRLQWZUYTZBJKN-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as epoxides. Epoxides are compounds containing a cyclic ether with three ring atoms(one oxygen and two carbon atoms).</description>
    <direct_parent>Epoxides</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Epoxides</class>
    <sub_class/>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Alkyl chlorides</alternative_parent>
      <alternative_parent>Dialkyl ethers</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organochlorides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alkyl chloride</substituent>
      <substituent>Alkyl halide</substituent>
      <substituent>Dialkyl ether</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organochloride</substituent>
      <substituent>Organohalogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxirane</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>epoxide</external_descriptor>
      <external_descriptor>organochlorine compound</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state>Liquid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.35</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.11</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>7.18e+01 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>-57.2 oC</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>0.68</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-4.2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>2-(chloromethyl)oxirane</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>92.524</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>92.002892489</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>ClCC1CO1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C3H5ClO</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C3H5ClO/c4-1-3-2-5-3/h3H,1-2H2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>BRLQWZUYTZBJKN-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>12.53</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>20.06</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>8.38</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>1</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>
  <pathways>
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    <reference>#&lt;Reference:0x000055ce32f1dde8&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32f1dbe0&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32f1d988&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32f1d758&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32f1d460&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32f1d230&gt;</reference>
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</compound>
