CHEBI:27869 - chloroacetic acid

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name chloroacetic acid
ChEBI ID CHEBI:27869
Definition A chlorocarboxylic acid that is acetic acid carrying a 2-chloro substituent.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:3622, CHEBI:23125
Supplier Information eMolecules:491354, ZINC000003860254
Download Molfile XML SDF
Formula C2H3ClO2
Net Charge 0
Average Mass 94.49700
Monoisotopic Mass 93.98216
InChI InChI=1S/C2H3ClO2/c3-1-2(4)5/h1H2,(H,4,5)
InChIKey FOCAUTSVDIKZOP-UHFFFAOYSA-N
SMILES OC(=O)CCl
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): alkylating agent
Highly reactive chemical that introduces alkyl radicals into biologically active molecules and thereby prevents their proper functioning. It could be used as an antineoplastic agent, but it might be very toxic, with carcinogenic, mutagenic, teratogenic, and immunosuppressant actions. It could also be used as a component of poison gases.
Application(s): herbicide
A substance used to destroy plant pests.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing chloroacetic acid (CHEBI:27869) has functional parent acetic acid (CHEBI:15366)
chloroacetic acid (CHEBI:27869) has role alkylating agent (CHEBI:22333)
chloroacetic acid (CHEBI:27869) has role herbicide (CHEBI:24527)
chloroacetic acid (CHEBI:27869) is a chlorocarboxylic acid (CHEBI:36685)
chloroacetic acid (CHEBI:27869) is a haloacetic acid (CHEBI:16277)
chloroacetic acid (CHEBI:27869) is conjugate acid of chloroacetate (CHEBI:23123)
Incoming N-(2,6-diethylphenyl)-2-chloroacetamide (CHEBI:136492) has functional parent chloroacetic acid (CHEBI:27869)
N-(2-ethyl-6-methylphenyl)-2-chloroacetamide (CHEBI:136494) has functional parent chloroacetic acid (CHEBI:27869)
N-[(5-acetyl-3-thienyl)methyl]-2-chloroacetamide semicarbazone (CHEBI:75056) has functional parent chloroacetic acid (CHEBI:27869)
chloroacetate (CHEBI:23123) is conjugate base of chloroacetic acid (CHEBI:27869)
chloroacetyl group (CHEBI:60669) is substituent group from chloroacetic acid (CHEBI:27869)
IUPAC Name
chloroacetic acid
Synonyms Sources
2-chloro-acetic acid LIPID MAPS
2-chloro-ethanoic acid LIPID MAPS
2-chloroacetic acid ChEBI
Acide chloracetique ChemIDplus
Acide chloroacetique ChemIDplus
Acide monochloracetique ChemIDplus
α-chloro-acetic acid ChEBI
CAA ChEBI
chloracetic acid NIST Chemistry WebBook
Chloroacetic acid KEGG COMPOUND
Chloroethanoic acid KEGG COMPOUND
Monochloressigsäure ChemIDplus
monochloroacetic acid NIST Chemistry WebBook
monochloroethanoic acid NIST Chemistry WebBook
Manual Xrefs Databases
C06755 KEGG COMPOUND
CHLOROACETIC-ACID MetaCyc
D07677 KEGG DRUG
HMDB0031331 HMDB
LMFA01090068 LIPID MAPS
monochloroacetic%20acid Alan Wood's Pesticides
R3W PDBeChem
View more database links
Registry Numbers Types Sources
605438 Reaxys Registry Number Reaxys
79-11-8 CAS Registry Number KEGG COMPOUND
79-11-8 CAS Registry Number NIST Chemistry WebBook
79-11-8 CAS Registry Number ChemIDplus
Citations Waiting for Citations
Last Modified
02 June 2017
General Comment
2011-03-25 An organic synthesis catalyst with mutagenic properties. A common phytotoxic aquatic contaminant, it is also a hepatocarcinogenic contaminant of the environmental pollutant trichloroethylene.