4-(4-Chloro-2-methylphenoxy)butanoic acid (CHEM000718)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (3)XML
Record Information
Version1.0
Creation Date2009-06-02 22:28:28 UTC
Update Date2016-11-09 01:08:21 UTC
Accession NumberCHEM000718
Identification
Common Name4-(4-Chloro-2-methylphenoxy)butanoic acid
ClassSmall Molecule
Description4-(4-Chloro-2-methylphenoxy)butanoic acid (MCPB, 2,4-MCPB) is a phenoxybutyric herbicide. In the United States it is registered for use on pea crops before flowering, for post-emergence control of broadleaf annual and perennial weeds including Canadian thistle, buttercup, mustard, purslane, ragweed, common lambsquarters, pigweed, smartweed, sowthistle, and morning glory. It has low to moderate acute toxicity, with kidney and liver effects as the main hazard concerns.
Contaminant Sources
  • HPV EPA Chemicals
  • IARC Carcinogens Group 3
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Aromatic Hydrocarbon
  • Ether
  • Industrial/Workplace Toxin
  • Organic Compound
  • Organochloride
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
4-(4-Chloro-O-tolyloxy)butyric acidChEBI
MCPBChEBI
4-(4-Chloro-O-tolyloxy)butyrateGenerator
4-(4-Chloro-2-methylphenoxy)butanoateGenerator
TropotoxMeSH
4-(4-Chloro-2-methylphenoxy)butyric acidMeSH
2-Methyl-4-chlorophenoxy gamma-butyric acid, sodium saltMeSH
MCPB-SodiumMeSH
2-Methyl-4-chlorophenoxy gamma-butyric acidMeSH
Chemical FormulaC11H13ClO3
Average Molecular Mass228.672 g/mol
Monoisotopic Mass228.055 g/mol
CAS Registry Number94-81-5
IUPAC Name4-(4-chloro-2-methylphenoxy)butanoic acid
Traditional NameMCPB
SMILESCC1=CC(Cl)=CC=C1OCCCC(O)=O
InChI IdentifierInChI=1S/C11H13ClO3/c1-8-7-9(12)4-5-10(8)15-6-2-3-11(13)14/h4-5,7H,2-3,6H2,1H3,(H,13,14)
InChI KeyLLWADFLAOKUBDR-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol ethers
Sub ClassNot Available
Direct ParentPhenol ethers
Alternative Parents
Substituents
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • Chlorobenzene
  • Halobenzene
  • Toluene
  • Aryl chloride
  • Monocyclic benzene moiety
  • Aryl halide
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • 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
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point100°C
Boiling PointNot Available
Solubility0.048 mg/mL at 25°C [YALKOWSKY,SH & DANNENFELSER,RM (1992)]
Predicted Properties
PropertyValueSource
Water Solubility0.17 g/LALOGPS
logP2.75ALOGPS
logP2.94ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)4.06ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity57.91 m³·mol⁻¹ChemAxon
Polarizability23.4 ųChemAxon
Number of Rings1ChemAxon
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, Positivesplash10-01t9-1290000000-07adf725c109c3738f4cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-015c-4920000000-0229ca65a4b564a69ef0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9400000000-70b0cefa0395926124c1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0690000000-2401b738a16f960b1622Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0920000000-9ce30369fdc1f5e72b89Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-2900000000-de071d4aa7c25fd26abfSpectrum
MSMass Spectrum (Electron Ionization)splash10-0006-5900000000-0d3b43ce51d5a4040c14Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesMCPB is a phenoxy herbicide produced as a sodium salt and an acid. MCPB is registered for use on pea crops before flowering, for post-emergence control of broadleaf annual and perennial weeds including Canadian thistle, buttercup, mustard, purslane, ragweed, common lambsquarters, pigweed, smartweed, sowthistle, and morning glory. (2)
Minimum Risk LevelNot Available
Health EffectsKidney and liver effects are the most prevalent hazard concerns for MCPB (2).
SymptomsNot Available
TreatmentTreatment may include washing any areas of contact, GI decontamination if swallowed, administering an IV and forced alkaline diuresis. (1)
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 ID81806
PubChem Compound ID7207
Kegg Compound IDC18529
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=22500447