<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-19 04:47:40 UTC</creation_date>
  <update_date>2026-08-21 20:56:09 UTC</update_date>
  <accession/>
  <common_name>1-(4-(Phenylazo)phenylazo)-2-naphthol</common_name>
  <class>SmallMolecule</class>
  <description>1-(4-(Phenylazo)phenylazo)-2-naphthol belongs to the azobenzenes, a class of organoheterocyclic compounds within the organic compounds. This compound has the chemical formula C22H16N4O and an average molecular weight of 352.40 g/mol. In industrial settings, it is utilized as a dye and as a fragrance.

The substance is associated with seven recorded sources of occurrence or release. Within the category of electrical and electronic equipment, it is found in magnets, antennas, discharge lamps, and gas filled discharge tubes with solid cathode. Additionally, it is linked to food, food processing, and cookware, specifically in the treatment of hops and the preparation of vinegar, wine, or sparkling wine.</description>
  <categories/>
  <types/>
  <synonyms>
    <synonym>Sudan III</synonym>
  </synonyms>
  <chemical_formula>C22H16N4O</chemical_formula>
  <average_molecular_weight>352.397</average_molecular_weight>
  <monisotopic_moleculate_weight>352.132411151</monisotopic_moleculate_weight>
  <iupac_name>1-[(E)-2-{4-[(E)-2-phenyldiazen-1-yl]phenyl}diazen-1-yl]naphthalen-2-ol</iupac_name>
  <traditional_iupac>oil red</traditional_iupac>
  <cas_registry_number>85-86-9</cas_registry_number>
  <smiles>OC1=C(\N=N\C2=CC=C(C=C2)\N=N\C2=CC=CC=C2)C2=CC=CC=C2C=C1</smiles>
  <inchi>InChI=1S/C22H16N4O/c27-21-15-10-16-6-4-5-9-20(16)22(21)26-25-19-13-11-18(12-14-19)24-23-17-7-2-1-3-8-17/h1-15,27H/b24-23+,26-25+</inchi>
  <inchikey>FHNINJWBTRXEBC-QSZPNPOGSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Azobenzenes</class>
    <sub_class/>
    <direct_parent>Azobenzenes</direct_parent>
    <alternate_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Azo compounds</alternative_parent>
      <alternative_parent>Benzene and substituted derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Naphthols and derivatives</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>2-naphthol</substituent>
      <substituent>Aromatic homopolycyclic compound</substituent>
      <substituent>Azo compound</substituent>
      <substituent>Azobenzene</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Naphthalene</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
    </substituents>
    <molecular_framework>Aromatic homopolycyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>azobenzenes</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>5.9</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>6.01</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.17</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>2.40e-03 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>7.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>11.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>0.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>1-[(E)-2-{4-[(E)-2-phenyldiazen-1-yl]phenyl}diazen-1-yl]naphthalen-2-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>352.397</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>352.132411151</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC1=C(\N=N\C2=CC=C(C=C2)\N=N\C2=CC=CC=C2)C2=CC=CC=C2C=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C22H16N4O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C22H16N4O/c27-21-15-10-16-6-4-5-9-20(16)22(21)26-25-19-13-11-18(12-14-19)24-23-17-7-2-1-3-8-17/h1-15,27H/b24-23+,26-25+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FHNINJWBTRXEBC-QSZPNPOGSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>69.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>113.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>39.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</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>
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  <hmdb_id/>
  <pubchem_compound_id>62331</pubchem_compound_id>
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  <chemspider_id>16736189</chemspider_id>
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