Fluoroacetic acid

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Fluoroacetic acid
Names
IUPAC name
Fluoroethanoic acid
Other names
2-Fluoroacetic acid
2-Fluoroethanoic acid
Cymonic acid
MFA
Monofluoroacetic acid
Properties
C2H3O2F
FCH2COOH
Molar mass 78.042 g/mol
Appearance White crystalline solid
Odor Odorless
Density 1.369 g/cm3
Melting point 35.2 °C (95.4 °F; 308.3 K)
Boiling point 165 °C (329 °F; 438 K)
Very soluble
Solubility Soluble in alcohols
Vapor pressure 1.27 mmHg at 25 °C
Acidity (pKa) 2.586
Hazards
Safety data sheet Sigma-Aldrich
Lethal dose or concentration (LD, LC):
4.68 mg/kg (rat, oral)
Related compounds
Related compounds
Acetic acid
Chloroacetic acid
Bromoacetic acid
Iodoacetic acid
Difluoroacetic acid
Trifluoroacetic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Fluoroacetic acid is a chemical compound with formula FCH2COOH. The compound itself has few uses in chemistry, but its sodium salt, sodium fluoroacetate, is often used as a pesticide. Di- and trifluoroacetic acid and their salts are far more commonly used instead, since they're more stable and far less toxic.

Properties

Chemical

Fluoroacetic acid and its salts will break down in the environment, releasing methyl fluoride (fluoromethane).

Physical

Fluoroacetic acid is a colorless crystalline solid, very soluble in water, and nearly odorless and tasteless.

Availability

Fluoroacetic acid is sold by lab suppliers, though due to its toxicity, it's difficult to acquire.

It's much more available as its sodium salt, which is used as pesticide in New Zeeland, Australia and United States.

Fluoroacetate salts, like potassium fluoroacetate occurs naturally in at least 40 plant species native to Australia, Brazil, and Africa, most common being Dichapetalum cymosum, commonly known as gifblaar (Afrikaans) or poison leaf, or Chailletia toxicaria. It is one of only five known organic fluorine-containing natural products.

Preparation

Can be prepared by adding a strong acid to the sodium salt.

Projects

  • Pesticide
  • Preparation of fluoromethane

Handling

Safety

Fluoroacetic acid is extremely poisonous and highly toxic to mammals and insects, though less so in birds. Ingestion is often fatal.

There is no known antidote, though glyceryl monoacetate has been shown to be effective in lab animal tests.

Storage

Fluoroacetic acid must be kept in an air-tight bottle, with a clear hazardous label.

Disposal

Fluoroacetic acid will break down in water to harmless side products. The enzyme fluoroacetate dehalogenase, which has been discovered in a soil bacterium, has been shown to be effective at decomposing this compound.

References

Relevant Sciencemadness threads