<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:10:39 UTC</creation_date>
  <update_date>2015-07-20 22:58:05 UTC</update_date>
  <accession>FDB013347</accession>
  <name>Phosphoryl chloride</name>
  <description>Etherification and esterification agent for modification of food starch

Like phosphate, phosphoryl chloride is tetrahedral in shape. It features three P-Cl bonds and one very strong P=O double bond, with an estimated bond dissociation energy of 533.5 kJ/mol. On the basis of bond length and electronegativity, the Schomaker-Stevenson rule suggests that the double bond form is very dominant (in contrast with POF3). The P=O bond does not resemble the ? bond in a carbonyl group as in a ketone. The appropriate description of the P-O interaction is a matter of long discussion. Older textbooks favor a description that invokes participation of the d-orbitals on phosphorus. Some of these d-orbitals project toward the O atom, overlapping with p-orbitals on oxygen. More modern texts seem to favor a description where the P-O ? bonding involves the ?* components of the P-Cl bonds. These descriptions do not consider a role for d-orbitals.; Phosphoryl chloride (commonly called phosphorus oxychloride) is a colourless liquid with the formula POCl3. It hydrolyses in moist air to phosphoric acid to release choking fumes of hydrogen chloride. It is manufactured industrially on a large scale from phosphorus trichloride and oxygen or phosphorus pentoxide. It is mainly used to make phosphate esters such as tricresyl phosphate.</description>
  <synonyms>
    <synonym>[PCl3O]</synonym>
    <synonym>Fosforoxychlorid</synonym>
    <synonym>OPCl3</synonym>
    <synonym>Oric chloride</synonym>
    <synonym>Oric trichloride</synonym>
    <synonym>Orous oxychloride</synonym>
    <synonym>Oroxidchlorid</synonym>
    <synonym>Oroxychlorid</synonym>
    <synonym>Oroxychloride</synonym>
    <synonym>Ortrichloridoxid</synonym>
    <synonym>Orus chloride</synonym>
    <synonym>Orus chloride oxide (pocl3)</synonym>
    <synonym>Orus oxide chloride</synonym>
    <synonym>Orus oxide trichloride</synonym>
    <synonym>Orus oxychloride</synonym>
    <synonym>Orus oxytrichloride</synonym>
    <synonym>Orus trichloride oxide</synonym>
    <synonym>Orus(V) oxide chloride</synonym>
    <synonym>Orus(V) oxychloride</synonym>
    <synonym>Orus(V) trichloride oxide</synonym>
    <synonym>Oryl chloride</synonym>
    <synonym>Oryl trichloride</synonym>
    <synonym>Orylchlorid</synonym>
    <synonym>Oxychlorid fosforecny</synonym>
    <synonym>Phosphoric chloride</synonym>
    <synonym>Phosphoric trichloride</synonym>
    <synonym>Phosphorous oxychloride</synonym>
    <synonym>Phosphoroxidchlorid</synonym>
    <synonym>Phosphoroxychlorid</synonym>
    <synonym>Phosphoroxychloride</synonym>
    <synonym>Phosphortrichloridoxid</synonym>
    <synonym>Phosphorus chloride</synonym>
    <synonym>Phosphorus chloride oxide (POCl3)</synonym>
    <synonym>Phosphorus oxide chloride</synonym>
    <synonym>Phosphorus oxide trichloride</synonym>
    <synonym>Phosphorus oxychloride</synonym>
    <synonym>Phosphorus oxychloride [UN1810] [Corrosive]</synonym>
    <synonym>Phosphorus oxytrichloride</synonym>
    <synonym>Phosphorus trichloride oxide</synonym>
    <synonym>Phosphorus(v) oxide chloride</synonym>
    <synonym>Phosphorus(v) oxychloride</synonym>
    <synonym>Phosphorus(v) trichloride oxide</synonym>
    <synonym>Phosphoryl trichloride</synonym>
    <synonym>Phosphorylchlorid</synonym>
    <synonym>POCl3</synonym>
    <synonym>Trichloridooxidoorus</synonym>
    <synonym>Trichloridooxidophosphorus</synonym>
    <synonym>Trichloroine oxide</synonym>
    <synonym>Trichloroorus oxide</synonym>
    <synonym>Trichlorooxoorus(V)</synonym>
    <synonym>Trichlorooxophosphorus(V)</synonym>
    <synonym>Trichlorophosphine oxide</synonym>
    <synonym>Trichlorophosphorus oxide</synonym>
    <synonym>Trichlorure de oryle</synonym>
    <synonym>Trichlorure de phosphoryle</synonym>
  </synonyms>
  <chemical_formula>Cl3OP</chemical_formula>
  <average_molecular_weight>153.332</average_molecular_weight>
  <monisotopic_moleculate_weight>151.875234255</monisotopic_moleculate_weight>
  <iupac_name>phosphoroyl trichloride</iupac_name>
  <traditional_iupac>phosphorus oxychloride</traditional_iupac>
  <cas_registry_number>10025-87-3</cas_registry_number>
  <smiles>ClP(Cl)(Cl)=O</smiles>
  <inchi>InChI=1S/Cl3OP/c1-5(2,3)4</inchi>
  <inchikey>XHXFXVLFKHQFAL-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of inorganic compounds known as halogen oxides. These are inorganic compounds containing an oxygen atom of an oxidation state of -2, in which the heaviest atom bonded to the oxygen is a halogen.</description>
    <direct_parent>Halogen oxides</direct_parent>
    <kingdom>Inorganic compounds</kingdom>
    <super_class>Homogeneous non-metal compounds</super_class>
    <class>Halogen organides</class>
    <sub_class>Halogen oxides</sub_class>
    <molecular_framework/>
    <alternative_parents>
      <alternative_parent>Inorganic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Halogen oxide</substituent>
      <substituent>Inorganic oxide</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>phosphorus coordination entity</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state>Liquid</state>
  <predicted_properties>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 1-1.5°</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>1.28</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>phosphoroyl trichloride</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>153.332</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>151.875234255</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>ClP(Cl)(Cl)=O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>Cl3OP</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/Cl3OP/c1-5(2,3)4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>XHXFXVLFKHQFAL-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>17.07</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>25.37</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>9.44</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>0</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>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>23743</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>149099</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>6681</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>6682</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>70443</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>70444</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>70445</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>128946</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>128947</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>128948</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2925085</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2925086</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2925087</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB34789</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id>30336</chebi_id>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce30e266d0&gt;</reference>
  </general_references>
  <foods>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
