Chloroacetic acid (CHEM004051)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 01:33:26 UTC
Update Date2026-04-17 19:11:54 UTC
Accession NumberCHEM004051
Identification
Common NameChloroacetic acid
ClassSmall Molecule
DescriptionA chlorocarboxylic acid that is acetic acid carrying a 2-chloro substituent.
Contaminant Sources
  • Clean Air Act Chemicals
  • Disinfection Byproducts
  • EAFUS Chemicals
  • FooDB Chemicals
  • HPV EPA Chemicals
  • OECD HPV Chemicals
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
2-Chloro-acetic acidChEBI
2-Chloro-ethanoic acidChEBI
2-Chloroacetic acidChEBI
Acide chloracetiqueChEBI
Acide chloroacetiqueChEBI
Acide monochloracetiqueChEBI
alpha-Chloro-acetic acidChEBI
CAAChEBI
Chloracetic acidChEBI
Chloroethanoic acidChEBI
MonochloressigsaeureChEBI
Monochloroacetic acidChEBI
Monochloroethanoic acidChEBI
AcetocaustinKegg
2-Chloro-acetateGenerator
2-Chloro-ethanoateGenerator
2-ChloroacetateGenerator
a-Chloro-acetateGenerator
a-Chloro-acetic acidGenerator
alpha-Chloro-acetateGenerator
Α-chloro-acetateGenerator
Α-chloro-acetic acidGenerator
ChloracetateGenerator
ChloroethanoateGenerator
MonochloroacetateGenerator
MonochloroethanoateGenerator
ChloroacetateGenerator
AcidomonocloroaceticoHMDB
alpha-Chloroacetic acidHMDB
CH2ClCOOHHMDB
Chloro-acetic acidHMDB
ChloroaceticHMDB
Chloroacetic acid (80% or less)HMDB
Chloroacetic acid crystallineHMDB
Chloroacetic acid, acsHMDB
Chloroacetic acid, liquidHMDB
Chloroacetic acid, moltenHMDB
Chloroacetic acid, solidHMDB
Chloroacetic acid, solid (dot)HMDB
Chloroacetic-acidHMDB
MCAHMDB
MonochloorazijnzuurHMDB
Monochloracetic acidHMDB
Monochloracetic acidacide monochloracetiqueHMDB
Sjphlqdiktp@HMDB
Chloroacetic acid, calcium saltHMDB
Chloroacetic acid, sodium (2:1) saltHMDB
Chloroacetic acid, sodium (5:2) saltHMDB
Chloroacetic acid, ammonium (2:1) saltHMDB
Chloroacetic acid, aluminum saltHMDB
Chloroacetic acid, ammonium saltHMDB
Chloroacetic acid, potassium (2:1) saltHMDB
Chloroacetic acid, silver saltHMDB
Chloroacetic acid, sodium saltHMDB
SODIUM chloroacetATEHMDB
Chloroacetic acid, calcium (3:1) saltHMDB
Chloroacetic acid, potassium saltHMDB
Chloroacetic acidMeSH
Chemical FormulaC2H3ClO2
Average Molecular Mass94.497 g/mol
Monoisotopic Mass93.982 g/mol
CAS Registry Number79-11-8
IUPAC Name2-chloroacetic acid
Traditional Namechloroacetic acid
SMILESOC(=O)CCl
InChI IdentifierInChI=1S/C2H3ClO2/c3-1-2(4)5/h1H2,(H,4,5)
InChI KeyFOCAUTSVDIKZOP-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
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 Solubility280 g/LALOGPS
logP0.18ALOGPS
logP0.31ChemAxon
logS0.47ALOGPS
pKa (Strongest Acidic)3.06ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity17.4 m³·mol⁻¹ChemAxon
Polarizability7.33 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, Positivesplash10-052f-9000000000-d7ad64391c96deb3de35Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00du-9200000000-940fedbd6b6f8c55c5a4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-aaf6edb2b5574f74bdcbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-38b0717f7c29f1ea92eaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9000000000-938f17816bbc5dcba3e4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-326c23d93ef6d226df1cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-fcac67e5e20790848ebdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-27e8aa335107dedd6cd7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002f-9000000000-56d70984d9778e4a12ffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002f-9000000000-b4c9c6e7cb283abccc40Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004j-9000000000-0c24059efae248d3d651Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-0825da4d9cf2fe857454Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-791aee9016391d12018fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-bc1d1ccda2784c87ec57Spectrum
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 IDHMDB0031331
FooDB IDFDB003394
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCHLOROACETIC-ACID
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkChloroacetic acid
Chemspider ID10772140
ChEBI ID27869
PubChem Compound ID300
Kegg Compound IDC06755
YMDB IDNot Available
ECMDB IDM2MDB004363
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12359395
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15033542
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=16647117
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=17490874
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23103613
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=25451595
7. Horisaki T, Yoshida E, Sumiya K, Takemura T, Yamane H, Nojiri H: Isolation and characterization of monochloroacetic acid-degrading bacteria. J Gen Appl Microbiol. 2011;57(5):277-84.
8. Gomha SM, Khalil KD: A convenient ultrasound-promoted synthesis of some new thiazole derivatives bearing a coumarin nucleus and their cytotoxic activity. Molecules. 2012 Aug 3;17(8):9335-47. doi: 10.3390/molecules17089335.
9. Baldessari A: Lipases as catalysts in synthesis of fine chemicals. Methods Mol Biol. 2012;861:445-56. doi: 10.1007/978-1-61779-600-5_25.
10. Zhang YK, Li W, Wu KY, Chen GG, Liang ZQ: Purification and characterization of an intracellular alpha-glucosidase with high transglycosylation activity from A. niger M-1. Prep Biochem Biotechnol. 2011;41(2):201-17. doi: 10.1080/10826068.2011.547384.
11. Ahuja M, Singh S, Kumar A: Evaluation of carboxymethyl gellan gum as a mucoadhesive polymer. Int J Biol Macromol. 2013 Feb;53:114-21. doi: 10.1016/j.ijbiomac.2012.10.033. Epub 2012 Nov 21.
12. Sa CS, Boaventura RA, Pereira IB: Analysis of haloacetic acids in water and air (aerosols) from indoor swimming pools using HS-SPME/GC/ECD. J Environ Sci Health A Tox Hazard Subst Environ Eng. 2012;47(2):176-83. doi: 10.1080/10934529.2012.640246.
13. Naderi M, Eshghi P, Cohan N, Miri-Moghaddam E, Yaghmaee M, Karimi M: Successful delivery in patients with FXIII deficiency receiving prophylaxis: report of 17 cases in Iran. Haemophilia. 2012 Sep;18(5):773-6. doi: 10.1111/j.1365-2516.2012.02785.x. Epub 2012 Mar 28.
14. Fomina EI: [A gas-chromatographic method of analysis of monochloroacetic acid and its sodium salt in the air, skin washings, protective clothing extracts and urine]. Gig Tr Prof Zabol. 1991;(12):39-41.
15. Tang S, Wang XM, Yang HW, Xie YF: Haloacetic acid removal by sequential zero-valent iron reduction and biologically active carbon degradation. Chemosphere. 2013 Jan;90(4):1563-7. doi: 10.1016/j.chemosphere.2012.09.046. Epub 2012 Oct 15.
16. Viozquez SF, Banon-Caballero A, Guillena G, Najera C, Gomez-Bengoa E: Enantioselective direct aldol reaction of alpha-keto esters catalyzed by (S(a))-binam-D-prolinamide under quasi solvent-free conditions. Org Biomol Chem. 2012 May 28;10(20):4029-35. doi: 10.1039/c2ob25224d. Epub 2012 Apr 18.
17. Chen CH, Chen SJ, Su CC, Yen CC, Tseng TJ, Jinn TR, Tang FC, Chen KL, Su YC, Lee kI, Hung DZ, Huang CF: Chloroacetic acid induced neuronal cells death through oxidative stress-mediated p38-MAPK activation pathway regulated mitochondria-dependent apoptotic signals. Toxicology. 2013 Jan 7;303:72-82. doi: 10.1016/j.tox.2012.10.008. Epub 2012 Oct 26.
18. Vaghani SS, Patel MM, Satish CS, Patel KM, Jivani NP: Synthesis and characterization of carboxymethyl chitosan hydrogel: application as pH-sensitive delivery for nateglinide. Curr Drug Deliv. 2012 Nov;9(6):628-36.
19. Mushtaque M, Avecilla F, Azam A: Synthesis, characterization and structure optimization of a series of thiazolidinone derivatives as Entamoeba histolytica inhibitors. Eur J Med Chem. 2012 Sep;55:439-48. doi: 10.1016/j.ejmech.2012.06.052. Epub 2012 Jul 4.
20. Li X, Ma J, Liu G, Fang J, Yue S, Guan Y, Chen L, Liu X: Efficient reductive dechlorination of monochloroacetic acid by sulfite/UV process. Environ Sci Technol. 2012 Jul 3;46(13):7342-9. doi: 10.1021/es3008535. Epub 2012 Jun 22.
21. Singh RK, Khatri OP: A scanning electron microscope based new method for determining degree of substitution of sodium carboxymethyl cellulose. J Microsc. 2012 Apr;246(1):43-52. doi: 10.1111/j.1365-2818.2011.03583.x. Epub 2011 Dec 12.
22. Meng L, Wu S, Ma F, Jia A, Hu J: Trace determination of nine haloacetic acids in drinking water by liquid chromatography-electrospray tandem mass spectrometry. J Chromatogr A. 2010 Jul 16;1217(29):4873-6. doi: 10.1016/j.chroma.2010.04.074. Epub 2010 May 24.
23. Kurita Y, Isogai A: N-Alkylations of chitosan promoted with sodium hydrogen carbonate under aqueous conditions. Int J Biol Macromol. 2012 Apr 1;50(3):741-6. doi: 10.1016/j.ijbiomac.2011.12.004. Epub 2011 Dec 17.
24. Iglesias E, Brandariz I: A further study of acetylacetone nitrosation. Org Biomol Chem. 2013 Feb 14;11(6):1059-64. doi: 10.1039/c2ob26073e. Epub 2013 Jan 3.
25. Naik TR, Naik HS, Prabhakara MC: One-pot solvent free synthesis and DNA binding studies of thieno[2,3-b]-1,8-naphthyridines. Prep Biochem Biotechnol. 2008;38(1):115-28.
26. Zhang B, Gong H, Lu S, Ni B, Liu M, Gao C, Huang Y, Han F: Synthesis and characterization of carboxymethyl potato starch and its application in reactive dye printing. Int J Biol Macromol. 2012 Nov;51(4):668-74. doi: 10.1016/j.ijbiomac.2012.07.003. Epub 2012 Jul 8.
27. Chapman T, Mahadevan D, Mahajan A, Perez-Temprano A, McDiarmid J: Iatrogenic full-thickness chemical burns from monochloracetic acid. J Burn Care Res. 2006 Jul-Aug;27(4):545-7.
28. Bruzzoniti MC, De Carlo RM, Sarzanini C, Caldarola D, Onida B: Novel insights in Al-MCM-41 precursor as adsorbent for regulated haloacetic acids and nitrate from water. Environ Sci Pollut Res Int. 2012 Nov;19(9):4176-83. doi: 10.1007/s11356-012-0900-6. Epub 2012 Apr 17.
29. Xu Q, Xu B, Qin C, Xia SJ, Gao NY, Tian FX, Li DP: [Chlorination byproducts formation potentials of typical nitrogenous organic compounds in water]. Huan Jing Ke Xue. 2011 Jul;32(7):1967-73.
30. Wang CX, Song QP: Removal of Cu(II) ions from aqueous solutions using N-carboxymethyl chitosan. Water Sci Technol. 2012;66(9):2027-32. doi: 10.2166/wst.2012.419.
31. Singh AV, Singh A, Nath LK: Microwave assisted synthesis and evaluation of modified pea starch as tablet superdisintegrant. Curr Drug Deliv. 2011 Mar;8(2):203-7.
32. Bidgoli H, Zamani A, Taherzadeh MJ: Effect of carboxymethylation conditions on the water-binding capacity of chitosan-based superabsorbents. Carbohydr Res. 2010 Dec 10;345(18):2683-9. doi: 10.1016/j.carres.2010.09.024. Epub 2010 Sep 25.
33. Ahuja M, Kumar A, Singh K: Synthesis, characterization and in vitro release behavior of carboxymethyl xanthan. Int J Biol Macromol. 2012 Dec;51(5):1086-90. doi: 10.1016/j.ijbiomac.2012.08.023. Epub 2012 Aug 27.
34. Gong P, Peng S, He J, Deng M, Jiang B, Wang K: One-step synthesis of glucose-branched galactomannan. Carbohydr Res. 2011 Sep 27;346(13):1973-7. doi: 10.1016/j.carres.2011.06.012. Epub 2011 Jun 16.
35. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.