<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:07:07 UTC</creation_date>
  <update_date>2025-11-18 23:01:47 UTC</update_date>
  <accession>FDB006384</accession>
  <name>2,4-Dinitrophenylhydrazone</name>
  <description>2,4-dinitrophenylhydrazone is a member of the class of compounds known as nitrobenzenes. Nitrobenzenes are compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro group. 2,4-dinitrophenylhydrazone is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 2,4-dinitrophenylhydrazone can be found in rice, which makes 2,4-dinitrophenylhydrazone a potential biomarker for the consumption of this food product. 2,4-Dinitrophenylhydrazine (DNPH, Brady's reagent, Borche's reagent) is the chemical compound C6H3(NO2)2NHNH2. Dinitrophenylhydrazine is a red to orange solid. It is a substituted hydrazine, and is often used to qualitatively test for carbonyl groups associated with aldehydes and ketones. The hydrazone derivatives can also be used as evidence toward the identity of the original compound. The melting point of the derivative is often used, with reference to a database of values, to determine the identity of a specific carbonyl compound. It is relatively sensitive to shock and friction; it is a shock explosive so care must be taken with its use. To reduce its explosive hazard, it is usually supplied wet .</description>
  <synonyms>
  </synonyms>
  <chemical_formula>C9H10N4O6</chemical_formula>
  <average_molecular_weight>270.201</average_molecular_weight>
  <monisotopic_moleculate_weight>270.060034058</monisotopic_moleculate_weight>
  <iupac_name>2-[2-(2,4-dinitrophenyl)hydrazin-1-ylidene]propane-1,3-diol</iupac_name>
  <traditional_iupac>2-[2-(2,4-dinitrophenyl)hydrazin-1-ylidene]propane-1,3-diol</traditional_iupac>
  <cas_registry_number/>
  <smiles>OCC(CO)=NNC1=CC=C(C=C1[N+]([O-])=O)[N+]([O-])=O</smiles>
  <inchi>InChI=1S/C9H10N4O6/c14-4-6(5-15)10-11-8-2-1-7(12(16)17)3-9(8)13(18)19/h1-3,11,14-15H,4-5H2</inchi>
  <inchikey>QPDZOBBTPQNZPW-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as nitrobenzenes. Nitrobenzenes are compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro group.</description>
    <direct_parent>Nitrobenzenes</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Benzene and substituted derivatives</class>
    <sub_class>Nitrobenzenes</sub_class>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Hydrazones</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Nitroaromatic compounds</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic oxoazanium compounds</alternative_parent>
      <alternative_parent>Organic zwitterions</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenylhydrazines</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Allyl-type 1,3-dipolar organic compound</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>C-nitro compound</substituent>
      <substituent>Hydrazone</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Nitroaromatic compound</substituent>
      <substituent>Nitrobenzene</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitro compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxoazanium</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic zwitterion</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenylhydrazine</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.97</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.13</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.98e-01 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>1.12</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>9.85</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>1.7</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>2-[2-(2,4-dinitrophenyl)hydrazin-1-ylidene]propane-1,3-diol</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>270.201</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>270.060034058</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>OCC(CO)=NNC1=CC=C(C=C1[N+]([O-])=O)[N+]([O-])=O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C9H10N4O6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C9H10N4O6/c14-4-6(5-15)10-11-8-2-1-7(12(16)17)3-9(8)13(18)19/h1-3,11,14-15H,4-5H2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>QPDZOBBTPQNZPW-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>151.13</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>63.98</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>23.99</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>8</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>3</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>105249</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>105250</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>105251</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>171711</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>171712</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>171713</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id/>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id/>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
  </general_references>
  <foods>
    <food>
      <name>Rice</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Oryza sativa</name_scientific>
      <ncbi_taxonomy_id>4530</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
