Chlorbenzylate (CHEM000549)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (47)XML
Record Information
Version1.0
Creation Date2009-03-06 18:59:14 UTC
Update Date2026-03-27 00:43:36 UTC
Accession NumberCHEM000549
Identification
Common NameChlorbenzylate
ClassSmall Molecule
DescriptionChlorobenzilate is a chlorinated hydrocarbon compound. It is used for mite control on citrus crops and in beehives. It has narrow insecticidal action, killing only ticks and mites. Products are available as emulsifiable concentrates or wettable powder formulations (3).
Contaminant Sources
  • Clean Air Act Chemicals
  • HPV EPA Chemicals
  • IARC Carcinogens Group 3
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Aromatic Hydrocarbon
  • Ester
  • Ether
  • Organic Compound
  • Organochloride
  • Pesticide
  • Pollutant
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Ethyl-4,4'-dichlorobenzilateKegg
Ethyl 2-hydroxy-2,2-bis(4-chlorophenyl)acetateKegg
Ethyl-4,4'-dichlorobenzilic acidGenerator
Ethyl 2-hydroxy-2,2-bis(4-chlorophenyl)acetic acidGenerator
Chlorbenzylic acidGenerator
Chemical FormulaC16H14Cl2O3
Average Molecular Mass325.187 g/mol
Monoisotopic Mass324.032 g/mol
CAS Registry Number510-15-6
IUPAC Nameethyl 2,2-bis(4-chlorophenyl)-2-hydroxyacetate
Traditional NameAcar
SMILESCCOC(=O)C(O)(C1=CC=C(Cl)C=C1)C1=CC=C(Cl)C=C1
InChI IdentifierInChI=1S/C16H14Cl2O3/c1-2-21-15(19)16(20,11-3-7-13(17)8-4-11)12-5-9-14(18)10-6-12/h3-10,20H,2H2,1H3
InChI KeyRAPBNVDSDCTNRC-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylmethanes
Direct ParentDiphenylmethanes
Alternative Parents
Substituents
  • Diphenylmethane
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Tertiary alcohol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Organohalogen compound
  • Organochloride
  • Organooxygen compound
  • Aromatic alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceTechnical chlorobenzilate, a brownish liquid, contains approximately 90% active compound. Pure chlorobenzilate is a yellow solid (3).
Experimental Properties
PropertyValue
Melting Point37°C
Boiling PointNot Available
Solubility0.013 mg/mL at 20°C [FURER,R & GEIGER,M (1977)]
Predicted Properties
PropertyValueSource
Water Solubility0.0055 g/LALOGPS
logP4.39ALOGPS
logP4.27ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)10.99ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity82.61 m³·mol⁻¹ChemAxon
Polarizability32.1 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0039000000-4b186c661f7a0b6e008cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fb9-0089000000-54f31a7ecd4c36a88711Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0290000000-edcc206f802107013997Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0049000000-45833e3d7c47118f0a69Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03k9-1987000000-18135986a0639e7dafe6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03dj-1980000000-58694eda553032bcc9f7Spectrum
MSMass Spectrum (Electron Ionization)splash10-0udi-3890000000-a7087fc3efc0369b93ffSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureDermal (L957
Mechanism of ToxicityAt least four mechanisms, possibly all functioning simultaneously. DDT reduces potassium transport across the membrane. DDT alters the porous channels through which sodium ions pass. These channels activate (open) normally but are inactivated (closed) slowly, thus interfering with the active transport of sodium out of the nerve axon during repolarization. DDT inhibits neuronal adenosine triphosphatases (ATPases), particularly Na+K+-ATPase, and Ca2+-ATPase which play vital roles in neuronal repolarization. DDT also inhibits the ability of calmodulin, a calcium mediator in nerves, to transport calcium ions that are essential for the release of neurotransmitters. All these inhibited functions reduce the rate of depolarization and increase the sensitivity of neurons to small stimuli that would not elicit a response in a fully depolarized neuron. (4)
MetabolismChlorobenzilate is metabolized by liver homogenates to para,para'-dichlorobenzilic acid; para, para'-dichlorobenzyhydrol; para-chlorobenzoic acid, and para, para'-dichlorobenzophenone. It is excreted in the urine (5).
Toxicity ValuesLD50: 2784-3880 mg/kg (Oral, Rat) (3) LD50: >10 000 mg/kg (Dermal, Rat) (3) LD50: >10 000 mg/kg (Dermal, Rabbit) (3)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (2)
Uses/SourcesChlorobenzilate is used for mite control on citrus crops and in beehives. It has narrow insecticidal action, killing only ticks and mites (3).
Minimum Risk LevelNot Available
Health EffectsNervous tension, liver and kidney damage, abnormal electrical activity of the brain (4, 3, 5)
SymptomsSymptoms of chlrobenzilate poisoning include muscle pains, ataxia, mild delirium, fever, and mental status changes progressing to a tonic-clonic seizure. Nausea, vomiting, and diarrhea may follow ingestion (5, 1).
TreatmentIn case of ingestion, consider cautious gastric lavage; it must be weighed against potential complications of bleeding or perforation. Activated charcoal binds most toxic agents and can decrease their systemic absorption if administered soon after ingestion. In case of inhalation, move patient to fresh air. Monitor for respiratory distress, and if cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with inhaled beta2 agonist and oral or parenteral corticosteroids. Irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes if the exposure occurred through eye contact. In case of dermal exposure, remove contaminated clothing and jewellery. Wash skin and hair thoroughly; do two soap and water washings. Leather absorbs pesticides. Hence, leather should not be worn in the presence of pesticides and all contaminated leather should be discarded. (6)
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 LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID10522
Kegg Compound IDC14574
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available