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): | |
| LD50 (Median dose)
|
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.
Contents
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 in solid form.
Availability
Fluoroacetic acid is sold by lab suppliers, though due to its high 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, albeit the amount of fluoroacetate in baits is fairly low.
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, followed by separation/extraction, then recrystallization from the solvent.
Projects
- Bird-resistant pesticide
- Preparation of fluoromethane
- Compound collecting
Handling
Safety
Fluoroacetic acid is extremely poisonous and highly toxic to mammals and insects, though less so in birds. Ingestion is often fatal, while exposure to sub-lethal doses may cause long-term effects.
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, preferably in a safe.
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.
