fluoroacetic acid
{{Chembox
| ImageFile1 = Fluoroacetic Acid V.1.svg
| ImageCaption2 = {{legend|rgb(64, 64, 64)|Carbon, C}}{{legend|white|Hydrogen, H}}{{legend|red|Oxygen, O}}{{legend|rgb(192, 256, 0)|Fluorine, F}}
| ImageFile2 = Fluoroacetic-acid-from-xtal-3D-balls.png
| PIN = Fluoroacetic acid
| OtherNames = {{ubl|2-Fluoroacetic acid|Cymonic acid|Fluoroethanoic acid|Monofluoroacetic acid}}
|Section1={{Chembox Identifiers
| CASNo = 144-49-0
| CASNo_Ref = {{cascite|correct|}}
| ChEBI = 30775
| Beilstein = 1739053
| Gmelin = 25730
| PubChem = 5237
| ChEMBL = 509273
| KEGG = C06108
| ChemSpiderID = 10205670
| 3DMet = B00905
| SMILES = FCC(O)=O
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = AP1JV9U41M
| EC_number = 205-631-7
| RTECS = AH5950000
| UNNumber = 2642
| InChI = 1/C2H3FO2/c3-1-2(4)5/h1H2,(H,4,5)
| InChIKey = QEWYKACRFQMRMB-UHFFFAOYAF
| StdInChI = 1S/C2H3FO2/c3-1-2(4)5/h1H2,(H,4,5)
| StdInChIKey = QEWYKACRFQMRMB-UHFFFAOYSA-N
}}
|Section2={{Chembox Properties
| Formula = {{chem2|FCH2CO2H}}
| C=2|H=3|F=1|O=2
| Appearance = White solid
| Density = 1.369 g/cm3
| MeltingPtC = 35.2
| BoilingPtC = 165
| Solubility = Soluble in water and ethanol
| pKa = 2.586{{contradict-inline|date=August 2024}}}}
|Section7={{Chembox Hazards
| MainHazards = Highly toxic and corrosive
| FlashPt =
| AutoignitionPt =
| GHSPictograms = {{GHS05}}{{GHS06}}{{GHS09}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|300|314|400}}
| PPhrases = {{P-phrases|260|264|270|273|280|301+310|301+330+331|303+361+353|304+340|305+351+338|310|321|330|363|391|405|501}}
| LD50 = 7 mg/kg (rat, oral)
}}
| Section8={{Chembox Related
| OtherCompounds = {{ubl|Difluoroacetic acid|Trifluoroacetic acid|Chloroacetic acid|Bromoacetic acid|Iodoacetic acid|Acetic acid|Haloacetic acids|Fluoroacetamide|Sodium fluoroacetate}}
}}
}}
Fluoroacetic acid is an organofluorine compound with the chemical formula {{chem2|FCH2CO2H|auto=1}}. It is a colorless solid that is noted for its relatively high toxicity.{{cite book |doi=10.1016/B978-008043405-6/50040-2|chapter=Highly-toxic fluorine compounds|title=Fluorine Chemistry at the Millennium|year=2000|last1=Timperley|first1=Christopher M.|pages=499–538|isbn=9780080434056}} The conjugate base, fluoroacetate occurs naturally in at least 40 plants in Australia, Brazil, and Africa. It is one of only five known organofluorine-containing natural products.{{cite book|author1=K.K. Jason Chan|author2=David O'Hagan|chapter=The Rare Fluorinated Natural Products and Biotechnological Prospects for Fluorine Enzymology |year=2012|title=Natural Product Biosynthesis by Microorganisms and Plants, Part B|series=Methods in Enzymology|volume=516|pages=219–235|doi=10.1016/B978-0-12-394291-3.00003-4|isbn=9780123942913|pmid=23034231}}
Toxicity
Fluoroacetic acid is a harmful metabolite of some fluorine-containing drugs (median lethal dose, LD50 = 10 mg/kg in humans). The most common metabolic sources of fluoroacetic acid are fluoroamines and fluoroethers. Fluoroacetic acid can disrupt the Krebs cycle.{{cite journal |last1=Kyzer |first1=Jillian L. |last2=Martens |first2=Marvin |title=Metabolism and Toxicity of Fluorine Compounds |journal=Chemical Research in Toxicology |date=15 March 2021 |volume=34 |issue=3 |pages=678–680 |doi=10.1021/acs.chemrestox.0c00439|pmid=33513303 |pmc=8023797}} The metabolite of fluoroacetic acid is Fluorocitric acid and is very toxic because it is not processable using aconitase in the Krebs cycle (where fluorocitrate takes place of citrate as the substrate). The enzyme is inhibited and the cycle stops working.{{cite book | last1 = Horák | first1 = J. | last2 = Linhart | first2 = I. | last3 = Klusoň |first3 = P. | title = Úvod do toxikologie a ekologie pro chemiky | language = Czech | edition = 1st | publisher = VŠCHT v Praze | location = Prague | year = 2004 | isbn = 80-7080-548-X}}
In contrast with fluoroacetic acid, difluoroacetic acid and trifluoroacetic acid are far less toxic. Its pKa is 2.66{{contradict-inline|date=August 2024}}, in contrast to 1.24 and 0.23 for the respective di- and trifluoroacetic acid.{{Ullmann |author=G. Siegemund |author2=W. Schwertfeger |author3=A. Feiring |author4=B. Smart |author5=F. Behr |author6=H. Vogel |author7=B. McKusick | title = Fluorine Compounds, Organic | doi = 10.1002/14356007.a11_349}}
Uses
Fluoroacetic acid is used to manufacture pesticides especially rodenticides such as sodium fluoroacetate (compound 1080). The overall market is projected to rise at a considerable rate during the forecast period, 2021 to 2027.{{cite web |author= Industry Research |title=Global Fluoroacetic Acid Market Share, Size 2021: Consumption Analysis By Applications, Future Demand, Top Leading Players, Competitive Situation and Emerging Trends, and Forecast to 2027 |url=https://www.marketwatch.com/press-release/global-fluoroacetic-acid-market-share-size-2021-consumption-analysis-by-applications-future-demand-top-leading-players-competitive-situation-and-emerging-trends-and-forecast-to-2027-2021-10-25 |publisher=MarketWatch |access-date=5 January 2022 |date=October 25, 2021|archive-url=https://web.archive.org/web/20220105024940/https://www.marketwatch.com/press-release/global-fluoroacetic-acid-market-share-size-2021-consumption-analysis-by-applications-future-demand-top-leading-players-competitive-situation-and-emerging-trends-and-forecast-to-2027-2021-10-25|archive-date=2022-01-05|url-status=dead}}
See also
References
{{Commons category}}
{{reflist}}
{{Fluoroacetates}}
Category:Fluorine-containing natural products