Chlorfenvinphos, cis- (CHEM008216)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 02:40:56 UTC
Update Date2016-11-09 01:13:45 UTC
Accession NumberCHEM008216
Identification
Common NameChlorfenvinphos, cis-
ClassSmall Molecule
DescriptionChlorfenvinphos is the common name of an organophosphorus compound that was widely used as an insecticide and an acaricide. The molecule itself can be described as an enol ester derived from dichloroacetophenone and diethylphosphonic acid. Chlorfenvinphos has been included in many products since its first use in 1963. However, because of its toxic effect as a cholinesterase inhibitor it has been banned in several countries, including the United States and the European Union. Its use in the United States was cancelled in 1991.The pure chemical is a colorless solid, but for commercial purposes, it is often marketed as an amber liquid. The insecticides, mostly used in liquid form, contain between 50% and 90% chlorfenvinphos. The substance easily mixes with acetone, ethanol, and propylene glycol. Furthermore, chlorfenvinphos is corrosive to metal and hydrolyzes in the environment.It is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.
Contaminant Sources
  • My Exposome Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
BirlaneMeSH
ChlorphenvinphosMeSH
ClofenvinfosMeSH
DermatonMeSH
[(Z)-2-chloro-1-(2,4-Dichlorophenyl)ethenyl] diethyl phosphoric acidGenerator
ChlorfenvinphosMeSH
(Z)-2-Chloro-1-(2,4-dichlorophenyl)ethenyl diethyl phosphoric acidGenerator
Chemical FormulaC12H14Cl3O4P
Average Molecular Mass359.560 g/mol
Monoisotopic Mass357.970 g/mol
CAS Registry Number18708-87-7
IUPAC Name(Z)-2-chloro-1-(2,4-dichlorophenyl)ethenyl diethyl phosphate
Traditional Namechlorfenvinphos
SMILES[H]\C(Cl)=C(\OP(=O)(OCC)OCC)C1=C(Cl)C=C(Cl)C=C1
InChI IdentifierInChI=1S/C12H14Cl3O4P/c1-3-17-20(16,18-4-2)19-12(8-13)10-6-5-9(14)7-11(10)15/h5-8H,3-4H2,1-2H3/b12-8-
InChI KeyFSAVDKDHPDSCTO-WQLSENKSSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dichlorobenzenes. Dichlorobenzenes are compounds containing a benzene with exactly two chlorine atoms attached to it.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassHalobenzenes
Direct ParentDichlorobenzenes
Alternative Parents
Substituents
  • 1,3-dichlorobenzene
  • Styrene
  • Dialkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Aryl halide
  • Aryl chloride
  • Chloroalkene
  • Haloalkene
  • Vinyl halide
  • Vinyl chloride
  • Organic oxide
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.017 g/LALOGPS
logP4.05ALOGPS
logP4.3ChemAxon
logS-4.3ALOGPS
pKa (Strongest Basic)-9.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area44.76 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity81.38 m³·mol⁻¹ChemAxon
Polarizability32.06 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT 21V, positivesplash10-0kdj-4940000000-021cd7e2a3b051419da9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT 25V, positivesplash10-052b-5921000000-171ee08ea370f7058007Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a7i-1829000000-2eb41c16236e39b9a92dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0119000000-fd237ae75cedf31bafdeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0imi-8910000000-2ecaf370dc038977cf09Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bwi-0719000000-d7c6d0bef13ce484e8a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06w9-0579000000-289b416292e2f3b43ac5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ul3-1965000000-0adf4069ddeca85b131bSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkChlorfenvinphos
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID5377784
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available