Trichloroacetic acid (CHEM003826)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (1)XML
Record Information
Version1.0
Creation Date2014-09-11 05:20:07 UTC
Update Date2026-04-14 18:09:09 UTC
Accession NumberCHEM003826
Identification
Common NameTrichloroacetic acid
ClassSmall Molecule
DescriptionTrichloroacetic acid (TCA; also known as trichloroethanoic acid) is an analogue of acetic acid in which the three hydrogen atoms of the methyl group have all been replaced by chlorine atoms.
Contaminant Sources
  • Disinfection Byproducts
  • HPV EPA Chemicals
  • IARC Carcinogens Group 2B
  • OECD HPV Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Household Toxin
  • Metabolite
  • Organic Compound
  • Organochloride
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
TCAChEBI
Trichloracetic acidChEBI
TrichloressigsaeureChEBI
Trichloroethanoic acidChEBI
TrichloroacetateKegg
Acido tricloroaceticoKegg
TrichloracetateGenerator
TrichloroethanoateGenerator
2,2,2-Trichloro-acetic acidHMDB
Acetic acid, trichloro- (solid)HMDB
Aceto-caustinHMDB
Acide trichloracetiqueHMDB
Amchem grass killerHMDB
CCL3coohHMDB
KonestaHMDB
Kyselina trichloroctovaHMDB
TKhUHMDB
TKhUKHMDB
TrichloorazijnzuurHMDB
TrichloressigsaureHMDB
Trichloro-acetic acidHMDB
Trichloroacetic acid (acd/name 4.0)HMDB
Trichloroacetic acid solid (dot)HMDB
Trichloroacetic acid solution (dot)HMDB
Trichloroacetate, rubidiumHMDB
Sodium trichloroacetateHMDB
Trichloracetique, acideHMDB
Rubidium trichloroacetateHMDB
Acid, trichloroaceticHMDB
Sanofi brand OF trichloroacetic acidHMDB
Trichloroacetate, sodiumHMDB
Chemical FormulaC2HCl3O2
Average Molecular Mass163.387 g/mol
Monoisotopic Mass161.904 g/mol
CAS Registry Number76-03-9
IUPAC Nametrichloroacetic acid
Traditional Nametrichloroacetic acid
SMILESOC(=O)C(Cl)(Cl)Cl
InChI IdentifierInChI=1S/C2HCl3O2/c3-2(4,5)1(6)7/h(H,6,7)
InChI KeyYNJBWRMUSHSURL-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as alpha-halocarboxylic acids. These are carboxylic acids containing a halogen atom bonded to the alpha carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAlpha-halocarboxylic acids and derivatives
Direct ParentAlpha-halocarboxylic acids
Alternative Parents
Substituents
  • Alpha-halocarboxylic acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Alkyl halide
  • Alkyl chloride
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
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 Point57.5 °C
Boiling Point195.5°C (383.9°F)
Solubility44 mg/mL at 25 °C
Predicted Properties
PropertyValueSource
Water Solubility2.12 g/LALOGPS
logP1.17ALOGPS
logP1.53ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)1.72ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity28.16 m³·mol⁻¹ChemAxon
Polarizability11.32 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0296-4900000000-7ca41d8f0edd786c2b1cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00xr-9620000000-7ddd39e1ab7e71700aabSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-2a1f08f2f9f0958b82bcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-63726390145b4934cc07Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0296-5900000000-c47c1239bda29fa232bbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-3b15586f346ff06bc481Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-1fc541b5cac29990c848Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-0900000000-4cf63adcb5470ed26fddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-37c55a7d3f64d0228a3eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-37c55a7d3f64d0228a3eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-2900000000-7849c6c36f8a17868f0fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-4aa5094ff4be0f74cd97Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-4aa5094ff4be0f74cd97Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-0900000000-4aa5094ff4be0f74cd97Spectrum
MSMass Spectrum (Electron Ionization)splash10-001j-9000000000-b5749368152821947a2bSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (5)
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDBSALT001528
HMDB IDHMDB0042048
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-9675
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTrichloroacetic_Acid
Chemspider ID10772050
ChEBI ID30956
PubChem Compound ID6421
Kegg Compound IDC11150
YMDB IDNot Available
ECMDB IDM2MDB004925
References
Synthesis ReferenceNot Available
MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12573897
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=16298895
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=16815816
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=16901594
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21269351
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=21332915
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=21457391
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=21497335
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=21523508
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=21529453
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=21549800
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=21716542
13. Song Y, Chidan Kumar CS, Akkurt M, Chandraju S, Li H: 1-[(4-Chloro-phen-yl)(phen-yl)meth-yl]piperazine-1,4-diium bis-(trichloro-acetate)-trichloro-acetic acid (1/1). Acta Crystallogr Sect E Struct Rep Online. 2012 Sep 1;68(Pt 9):o2695-6. doi: 10.1107/S1600536812034794. Epub 2012 Aug 11.
14. Husek P, Svagera Z, Hanzlikova D, Simek P: Survey of several methods deproteinizing human plasma before and within the chloroformate-mediated treatment of amino/carboxylic acids quantitated by gas chromatography. J Pharm Biomed Anal. 2012 Aug-Sep;67-68:159-62. doi: 10.1016/j.jpba.2012.04.027. Epub 2012 May 7.
15. Arjunan V, Marchewka MK, Pietraszko A, Kalaivani M: X-ray diffraction, vibrational and quantum chemical investigations of 2-methyl-4-nitroanilinium trichloroacetate trichloroacetic acid. Spectrochim Acta A Mol Biomol Spectrosc. 2012 Nov;97:625-38. doi: 10.1016/j.saa.2012.07.018. Epub 2012 Jul 16.
16. Valencia DP, Astudillo PD, Galano A, Gonzalez FJ: Self-decarboxylation of trichloroacetic acid redox catalyzed by trichloroacetate ions in acetonitrile solutions. Org Biomol Chem. 2013 Jan 14;11(2):318-25. doi: 10.1039/c2ob26961a. Epub 2012 Nov 19.