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Record Information
Version1.0
Creation date2010-04-08 22:10:39 UTC
Update date2015-07-20 22:58:05 UTC
Primary IDFDB013347
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePhosphoryl chloride
DescriptionEtherification 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.
CAS Number10025-87-3
Structure
Thumb
Synonyms
SynonymSource
[PCL3O]ChEBI
Phosphoric trichlorideChEBI
PhosphoroxidchloridChEBI
PhosphoroxychloridChEBI
PhosphortrichloridoxidChEBI
Phosphorus oxychlorideChEBI
Phosphorus trichloride oxideChEBI
Phosphorus(V) trichloride oxideChEBI
PhosphorylchloridChEBI
POCl3ChEBI
Trichlorure de phosphoryleChEBI
FosforoxychloridHMDB
OPCl3HMDB
Oxychlorid fosforecnyHMDB
Phosphoric chlorideHMDB
Phosphorous oxychlorideHMDB
PhosphoroxychlorideHMDB
Phosphorus chlorideHMDB
Phosphorus chloride oxide (pocl3)HMDB
Phosphorus oxide chlorideHMDB
Phosphorus oxide trichlorideHMDB
Phosphorus oxytrichlorideHMDB
Phosphorus(V) oxide chlorideHMDB
Phosphorus(V) oxychlorideHMDB
Phosphoryl trichlorideHMDB
TrichloridooxidophosphorusHMDB
Trichlorooxophosphorus(V)HMDB
Trichlorophosphine oxideHMDB
Trichlorophosphorus oxideHMDB
Phosphoryl chlorideChEBI
[PCl3O]biospider
Oric chlorideHMDB
Oric trichlorideChEBI
Orous oxychlorideHMDB
OroxidchloridChEBI
OroxychloridChEBI
OroxychlorideHMDB
OrtrichloridoxidChEBI
Orus chlorideHMDB
Orus chloride oxide (pocl3)HMDB
Orus oxide chlorideHMDB
Orus oxide trichlorideHMDB
Orus oxychlorideChEBI
Orus oxytrichlorideHMDB
Orus trichloride oxideChEBI
Orus(V) oxide chlorideHMDB
Orus(V) oxychlorideHMDB
Orus(V) trichloride oxideChEBI
Oryl chlorideChEBI
Oryl trichlorideHMDB
OrylchloridChEBI
Phosphorus chloride oxide (POCl3)biospider
Phosphorus oxychloride [UN1810] [Corrosive]biospider
Phosphorus(v) oxide chloridebiospider
Phosphorus(v) oxychloridebiospider
Phosphorus(v) trichloride oxidebiospider
TrichloridooxidoorusHMDB
Trichloroine oxideHMDB
Trichloroorus oxideHMDB
Trichlorooxoorus(V)HMDB
Trichlorure de oryleChEBI
Predicted Properties
PropertyValueSource
logP1.28ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity25.37 m³·mol⁻¹ChemAxon
Polarizability9.44 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaCl3OP
IUPAC namephosphoroyl trichloride
InChI IdentifierInChI=1S/Cl3OP/c1-5(2,3)4
InChI KeyXHXFXVLFKHQFAL-UHFFFAOYSA-N
Isomeric SMILESClP(Cl)(Cl)=O
Average Molecular Weight153.332
Monoisotopic Molecular Weight151.875234255
Classification
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.
KingdomInorganic compounds
Super ClassHomogeneous non-metal compounds
ClassHalogen organides
Sub ClassHalogen oxides
Direct ParentHalogen oxides
Alternative Parents
Substituents
  • Halogen oxide
  • Inorganic oxide
Molecular FrameworkNot Available
External Descriptors
Ontology
Disposition

Source:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionCl 69.36%; O 10.43%; P 20.20%DFC
Melting PointMp 1-1.5°DFC
Boiling PointBp 107-107.5°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd254 1.67DFC
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSPhosphoryl chloride, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0udi-0900000000-5c46befa3028eba4a34dSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-8ba138ebff631ad13b8fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-8ba138ebff631ad13b8fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0900000000-8ba138ebff631ad13b8fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-dbc9a67946553812d424Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-dbc9a67946553812d424Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0900000000-dbc9a67946553812d424Spectrum
NMRNot Available
ChemSpider ID23198
ChEMBL IDCHEMBL3183103
KEGG Compound IDNot Available
Pubchem Compound ID24813
Pubchem Substance IDNot Available
ChEBI ID30336
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34789
CRC / DFC (Dictionary of Food Compounds) IDHTJ19-E:HTJ19-E
EAFUS ID3034
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDPhosphoryl_chloride
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference