ContaminantDB: Fluoroacetic acid

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (2)XML

Record Information

Version

1.0

Creation Date

2009-07-30 17:58:52 UTC

Update Date

2026-03-31 16:51:32 UTC

Accession Number

CHEM002516

Identification

Common Name

Fluoroacetic acid

Class

Small Molecule

Description

Fluoroacetate is highly toxic to mammals and insects and it is used as a pesticide. The more common fluorinated acetic acid, trifluoroacetic acid and its sodium salt are far less toxic. (5)

Contaminant Sources

Clean Air Act Chemicals
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Organic Compound
Organofluoride
Pesticide
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Acide-monofluoracetique	ChEBI
Cymonic acid	ChEBI
Gifblaar poison	ChEBI
HFA	ChEBI
Monofluoressigsaure	ChEBI
Monofluoroacetic acid	ChEBI
UN 2642	ChEBI
Cymonate	Generator
Monofluoroacetate	Generator
Fluoroacetate	Generator
Fluoroacetic acid, calcium salt	MeSH
Fluoroacetic acid, potassium salt	MeSH
Fluoroacetic acid, sodium salt	MeSH
Fluoroacetic acid, aluminum salt	MeSH
Fluoroacetic acid, mercury (2+) salt	MeSH
Fluoroacetic acid, 18F-labeled	MeSH
Fluoroacetic acid, ammonium salt	MeSH
Fluoroacetic acid, ammonium salt, 2-(14)C-labeled	MeSH
Fluoroacetic acid, lead (+4) salt	MeSH
Sodium (18F)fluoroacetate	MeSH
Sodium fluoroacetate	MeSH
Compound 1080	MeSH
Fluoroacetic acid, barium salt	MeSH
Fluoroacetic acid, cadmium salt	MeSH
Fluoroacetic acid, copper (2+) salt	MeSH
Fluoroacetic acid, magnesium salt	MeSH
Fluoroacetic acid, terbium (+3) salt	MeSH

Chemical Formula

C₂H₃FO₂

Average Molecular Mass

78.042 g/mol

Monoisotopic Mass

78.012 g/mol

CAS Registry Number

144-49-0

IUPAC Name

2-fluoroacetic acid

Traditional Name

fluoroacetic acid

SMILES

OC(=O)CF

InChI Identifier

InChI=1S/C2H3FO2/c3-1-2(4)5/h1H2,(H,4,5)

InChI Key

QEWYKACRFQMRMB-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Alpha-halocarboxylic acids and derivatives

Direct Parent

Alpha-halocarboxylic acids

Alternative Parents

Substituents

Alpha-halocarboxylic acid
Monocarboxylic acid or derivatives
Carboxylic acid
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organofluoride
Organohalogen compound
Carbonyl group
Alkyl halide
Alkyl fluoride
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

organofluorine compound (CHEBI:30775 )
haloacetic acid (CHEBI:30775 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

EC 4.2.1.3 (aconitate hydratase) inhibitor

Chemical Roles

EC 4.2.1.3 (aconitate hydratase) inhibitor

Physical Properties

State

Solid

Appearance

Odourless colourless crystals. (3)

Experimental Properties

Property	Value
Melting Point	35.2°C
Boiling Point	165 °C (at 760 mm Hg)
Solubility	50 mg/L (at 25 °C)

Predicted Properties

Property	Value	Source
Water Solubility	87.8 g/L	ALOGPS
logP	-0.31	ALOGPS
logP	-0.15	ChemAxon
logS	0.05	ALOGPS
pKa (Strongest Acidic)	3.13	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	12.65 m³·mol⁻¹	ChemAxon
Polarizability	5.42 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a7l-9000000000-f6eebc233f0ccc84cc91	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-9000000000-efaaf137ab92debe74d9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-9000000000-56c0285d4c34c07b9f1f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-9000000000-3205e2491a65ed06d003	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-9000000000-87030bad0d891f57d237	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-04da7eacb8d38c4f784f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-342eba1db056a504806d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01t9-9000000000-fb45b97f33fafe6d949a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03fr-9000000000-e462b6852fa12c30078e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03e9-9000000000-86fe2c74e12e5cba4280	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-9000000000-a07d8a8594b9e329861c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-35c3b7c06403b40833aa	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-834139431d8139878eca	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-001j-9000000000-47dd2c2d56467d877eab	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Inhalation (4)

Mechanism of Toxicity

Fluoroacetate is similar to acetate, which has a pivotal role in cellular metabolism. Fluoroacetate disrupts the citric acid cycle by combining with coenzyme A to form fluoroacetyl CoA. Fluoroacetyl CoA then reacts with citrate synthase to produce fluorocitrate. A metabolite of fluorocitrate binds very tightly to aconitase, thereby halting the citric acid cycle. This inhibition results in an accumulation of citrate in the blood which deprives cells of energy. (5) (1) (2)

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

This is a man-made compound that is used as a pesticide.

Minimum Risk Level

Not Available

Health Effects

Fluoroacetic acid is corrosive to the eyes, the skin and the respiratory tract. It may cause effects on the cardiovascular system, central nervous system, kidneys, resulting in impaired functions including cardiac and renal failure. Exposure may result in death. (4) (3)

Symptoms

Cough, laboured breathing, nausea, sore throat, vomiting, excessive salivation, numbness and tingling sensation, arrhythmia are observed after fluoroacetic acid inhalation; redness, serious skin burns, pain occur after skin contact; abdominal pain and convulsions in case of ingestion; blurred vision and severe deep burns if eye contact. These symptoms may be delayed. (4)

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0252369

FooDB ID

Not Available

Phenol Explorer ID