chloroacetic acid (CHEBI:27869)

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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

Download	Molfile XML SDF

Formula

C2H3ClO2

Net Charge

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.

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

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.