<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:08:17 UTC</creation_date>
  <update_date>2018-05-29 00:44:33 UTC</update_date>
  <accession>FDB008867</accession>
  <name>4-(Dimethylamino)azobenzene</name>
  <description>Formerly used as a food dye, use discontinued

Methyl yellow, or C.I. 11020, is a chemical compound which may be used as a pH indicator. In aqueous solution at low pH, methyl yellow appears red. Between pH 2.9 and 4.0, methyl yellow undergoes a transition, to become yellow above pH 4.0. As "butter yellow" the agent had been used as a food additive before its toxicity was recognized (Opie EL).</description>
  <synonyms>
    <synonym>4-(Dimethylamino)azobenzene</synonym>
    <synonym>4-(Dimethylamino)phenylazobenzene</synonym>
    <synonym>4-(N,N-Dimethylamino)azobenzene</synonym>
    <synonym>4-(Phenylazo)-N,N-dimethylaniline</synonym>
    <synonym>Butter yellow</synonym>
    <synonym>C.I. 11020</synonym>
    <synonym>C.I. Solvent yellow 2</synonym>
    <synonym>Dimethyl yellow</synonym>
    <synonym>Methyl yellow</synonym>
    <synonym>N,N-Dimethyl-4-(phenylazo)aniline</synonym>
    <synonym>N,N-Dimethyl-4-(phenylazo)benzenamine, 9CI</synonym>
    <synonym>N,N-Dimethyl-p-(phenylazo)aniline, 8CI</synonym>
    <synonym>p-Dimethylaminoazobenzene</synonym>
    <synonym>para-(Dimethylamino)azobenzene</synonym>
  </synonyms>
  <chemical_formula>C14H15N3</chemical_formula>
  <average_molecular_weight>225.289</average_molecular_weight>
  <monisotopic_moleculate_weight>225.126597495</monisotopic_moleculate_weight>
  <iupac_name>N,N-dimethyl-4-[(Z)-2-phenyldiazen-1-yl]aniline</iupac_name>
  <traditional_iupac>N,N-dimethyl-4-[(Z)-2-phenyldiazen-1-yl]aniline</traditional_iupac>
  <cas_registry_number>60-11-7</cas_registry_number>
  <smiles>CN(C)C1=CC=C(C=C1)\N=N/C1=CC=CC=C1</smiles>
  <inchi>InChI=1S/C14H15N3/c1-17(2)14-10-8-13(9-11-14)16-15-12-6-4-3-5-7-12/h3-11H,1-2H3/b16-15-</inchi>
  <inchikey>JCYPECIVGRXBMO-NXVVXOECSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as azobenzenes. These are organonitrogen aromatic compounds that contain a central azo group, where each nitrogen atom is conjugated to a benzene ring.</description>
    <direct_parent>Azobenzenes</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Azobenzenes</class>
    <sub_class/>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Aniline and substituted anilines</alternative_parent>
      <alternative_parent>Azo compounds</alternative_parent>
      <alternative_parent>Dialkylarylamines</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Amine</substituent>
      <substituent>Aniline or substituted anilines</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Azo compound</substituent>
      <substituent>Azobenzene</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Dialkylarylamine</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
      <substituent>Tertiary aliphatic/aromatic amine</substituent>
      <substituent>Tertiary amine</substituent>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.63</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.77</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>3.83e-02 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 117°</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>4.49</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>3.58</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>N,N-dimethyl-4-[(Z)-2-phenyldiazen-1-yl]aniline</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>225.289</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>225.126597495</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CN(C)C1=CC=C(C=C1)\N=N/C1=CC=CC=C1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C14H15N3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C14H15N3/c1-17(2)14-10-8-13(9-11-14)16-15-12-6-4-3-5-7-12/h3-11H,1-2H3/b16-15-</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>JCYPECIVGRXBMO-NXVVXOECSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>27.96</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>74.81</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>25.02</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>3</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>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310489</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310490</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310491</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>355219</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>355220</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>355221</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2421123</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2421124</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2421125</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2544502</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2544503</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2544504</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>19987</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>136487</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>144221</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB32141</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id>17903</chebi_id>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce309ab420&gt;</reference>
  </general_references>
  <foods>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
