2-Fluoroethanol

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2-Fluoroethanol [1]
2-Fluoroethanol-2D-by-AHRLS-2012.png
2-fluoroethanol-from-xtal-3D-bs-17.png
2-fluoroethanol-from-xtal-3D-sf.png
Names
Preferred IUPAC name
2-Fluoroethan-1-ol
Other names
Ethylene fluorohydrine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.006.128 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C2H5FO/c3-1-2-4/h4H,1-2H2 Yes check.svgY
    Key: GGDYAKVUZMZKRV-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C2H5FO/c3-1-2-4/h4H,1-2H2
    Key: GGDYAKVUZMZKRV-UHFFFAOYAT
  • FCCO
Properties
C2H5FO
Molar mass 64.059 g·mol−1
Odor Musky, rather tart [2]
Density 1.1040 g cm−3 [1]
Melting point −26.3 °C (−15.3 °F; 246.8 K) [1]
Boiling point 103.5 °C (218.3 °F; 376.6 K) [1]
miscible [1]
Solubility Soluble in ethanol, ethyl ether, acetone
Vapor pressure 19 mbar (15 °C) [1]
Acidity (pKa)14.74 (predicted) [3]
Hazards
GHS labelling:
GHS-pictogram-skull.svg GHS-pictogram-flamme.svg
H226, H300+H310+H330
P210, P233, P240, P241, P242, P243, P260, P262, P264, P270, P271, P280, P284, P301+P310+P330, P303+P361+P353, P304+P340+P310, P363, P370+P378, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704.svgHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
4
2
1
Flash point 34 °C (93.2 °F; 307.15 K)
Related compounds
Other anions
2-Chloroethanol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

2-Fluoroethanol is the organic compound with the formula CH2FCH2OH. This colorless liquid is one of the simplest stable fluorinated alcohols. It was once used as a pesticide. The related difluoro- and trifluoroethanols are far less dangerous. [4]

Contents

Synthesis

2-Fluoroethanol was originally synthesized by treating 2-chloroethanol with potassium fluoride, in a simple Finkelstein reaction. [5] The product has a lower boiling point that the starting material and may be conveniently isolated by distillation.

ClCH2CH2OH + KF → FCH2CH2OH + KCl

Similar procedures start from (1,3)-dioxolan-2-one [6] and from 2-bromoethanol. [7]

Structure and reactivity

Hydrogen bonding stabilizes the gauche conformer. [8] [9]

In a basic solution, 2-fluoroethanol undergoes dehydrofluorination, giving acetaldehyde. [10]

Reaction of 2-fluoroethanol with trifluoromethanesulfonic anhydride in the presence of base gives the triflate ester. [11]

PET radiotracers

2-[18F]-fluoroethoxy group is a common moiety in the structures of radiotracers used with PET. Such radiotracers include fluoroethyl-l-tyrosine 1-(2-[18F]-fluoroethoxy)-4-nitrobenzene and [18F]-fluoroethyl 4-fluorobenzoate, being a [18F]fluoroalkyl ether and ester respectively. [12] [11]

Metabolism

It was patented as a rodenticide in Germany in 1935. [13] In rats, it was found that fluoroethanol induced a similar toxicity as that of fluoroacetate, known to metabolize to fluorocitrate to exert the toxic effect. [13]

2-Fluoroethanol is converted by alcohol dehydrogenase (ADH) using nicotinamide adenine dinucleotide (NAD+) as cofactor, [13] ultimately leading to the formation of fluoroacetaldehyde and then fluoroacetate. [13]

Fluoroacetate is a precursor to fluorocitrate, [14] an inhibitor of aconitase, an enzyme that participates in the TCA cycle. [15]

Toxicity

Reported effects of 2-fluoroethanol are epigastric distress effects, such as vomiting, and central nervous effects, such as auditory hallucinations, numbness feeling of the face or nose. Both these types of effects occur gradually after being exposed to 2-fluoroethanol for several hours. Some more severe reactions of the human body to 2-fluoroethanol can be respiratory failure and epileptiform convulsions or seizures, leading to dysfunctions in the heart mechanism. From the early 20th century, there are multiple reports of deaths caused by 2-fluoroethanol. [16]

2-Fluoroethanol is also toxic to other animals with LD50 ranging from 7 to 1500 mg/kg bodyweight.

See also

Related Research Articles

<span class="mw-page-title-main">Sodium fluoroacetate</span> Chemical compound

Sodium fluoroacetate, also known as compound 1080, is an organofluorine chemical compound with the chemical formula FCH2CO2Na. It is the sodium salt of fluoroacetic acid. It contains sodium cations Na+ and fluoroacetate anions FCH2CO−2. This colourless salt has a taste similar to that of table salt and is used as a rodenticide.

<span class="mw-page-title-main">Bromobenzene</span> Chemical compound

Bromobenzene is an aryl bromide and the simplest of the bromobenzenes, consisting of a benzene ring substituted with one bromine atom. Its chemical formula is C6H5Br. It is a colourless liquid although older samples can appear yellow. It is a reagent in organic synthesis.

Fluorodeoxyglucose (<sup>18</sup>F) Chemical compound

[18F]Fluorodeoxyglucose (INN), or fluorodeoxyglucose F 18, also commonly called fluorodeoxyglucose and abbreviated [18F]FDG, 2-[18F]FDG or FDG, is a radiopharmaceutical, specifically a radiotracer, used in the medical imaging modality positron emission tomography (PET). Chemically, it is 2-deoxy-2-[18F]fluoro-D-glucose, a glucose analog, with the positron-emitting radionuclide fluorine-18 substituted for the normal hydroxyl group at the C-2 position in the glucose molecule.

<span class="mw-page-title-main">Copper(II) fluoride</span> Chemical compound

Copper(II) fluoride is an inorganic compound with the chemical formula CuF2. The anhydrous form is a white, ionic, crystalline, hygroscopic salt with a distorted rutile-type crystal structure, similar to other fluorides of chemical formulae MF2 (where M is a metal). The dihydrate, CuF2·2H2O, is blue in colour.

<span class="mw-page-title-main">Diisopropyl fluorophosphate</span> Chemical compound

Diisopropyl fluorophosphate (DFP) or Isoflurophate is an oily, colorless liquid with the chemical formula C6H14FO3P. It is used in medicine and as an organophosphorus insecticide. It is stable, but undergoes hydrolysis when subjected to moisture.

<span class="mw-page-title-main">Fluoroacetic acid</span> Chemical compound

Fluoroacetic acid is a organofluorine compound with the chemical formula FCH2CO2H. It is a colorless solid that is noted for its relatively high toxicity. 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.

<span class="mw-page-title-main">Fluorine-18</span> Isotope of fluorine emitting a positron

Fluorine-18 (18F) is a fluorine radioisotope which is an important source of positrons. It has a mass of 18.0009380(6) u and its half-life is 109.771(20) minutes. It decays by positron emission 96.7% of the time and electron capture 3.3% of the time. Both modes of decay yield stable oxygen-18.

Organofluorine chemistry describes the chemistry of organofluorine compounds, organic compounds that contain a carbon–fluorine bond. Organofluorine compounds find diverse applications ranging from oil and water repellents to pharmaceuticals, refrigerants, and reagents in catalysis. In addition to these applications, some organofluorine compounds are pollutants because of their contributions to ozone depletion, global warming, bioaccumulation, and toxicity. The area of organofluorine chemistry often requires special techniques associated with the handling of fluorinating agents.

<span class="mw-page-title-main">Diethylaminosulfur trifluoride</span> Chemical compound

Diethylaminosulfur trifluoride (DAST) is the organosulfur compound with the formula Et2NSF3. This liquid is a fluorinating reagent used for the synthesis of organofluorine compounds. The compound is colourless; older samples assume an orange colour.

Fluorination with aminosulfuranes is a chemical reaction that transforms oxidized organic compounds into organofluorine compounds. Aminosulfuranes selectively exchange hydroxyl groups for fluorine, but are also capable of converting carbonyl groups, halides, silyl ethers, and other functionality into organofluorides.

<span class="mw-page-title-main">Biological aspects of fluorine</span>

Fluorine may interact with biological systems in the form of fluorine-containing compounds. Though elemental fluorine (F2) is very rare in everyday life, fluorine-containing compounds such as fluorite occur naturally as minerals. Naturally occurring organofluorine compounds are extremely rare. Man-made fluoride compounds are common and are used in medicines, pesticides, and materials. Twenty percent of all commercialized pharmaceuticals contain fluorine, including Lipitor and Prozac. In many contexts, fluorine-containing compounds are harmless or even beneficial to living organisms; in others, they are toxic.

<span class="mw-page-title-main">1-Bromo-4-fluorobenzene</span> Chemical compound

4-Fluorobromobenzene is a mixed aryl halide (aryl fluoride and aryl bromide) with the formula C6H4BrF. It is a derivative of benzene, with a bromine atom bonded para to a fluorine atom. It has uses as a precursor to some pharmaceuticals, as an agrochemical intermediate, and in organic synthesis. It is a colorless liquid of low acute toxicity.

1,2-Difluoroethane is a saturated hydrofluorocarbon containing an atom of fluorine attached to each of two carbons atoms. The formula can be written CH2FCH2F. It is an isomer of 1,1-difluoroethane. It has a HFC name of HFC-152 with no letter suffix. When cooled to cryogenic temperatures it can have different conformers, gauche and trans. In the liquid form these are about equally abundant and easily interconvert. As a gas it is mostly the gauche form.

<span class="mw-page-title-main">Methyl fluoroacetate</span> Chemical compound

Methyl fluoroacetate (MFA) is an organic compound with the chemical formula FCH2CO2CH3. It is an extremely toxic methyl ester of fluoroacetic acid. It is a colorless, odorless liquid at room temperature. It is used as a laboratory chemical and as a rodenticide. Because of its extreme toxicity, MFA was studied for potential use as a chemical weapon.

<span class="mw-page-title-main">Peter J. H. Scott</span>

Peter J. H. Scott FRSC CChem is a British and American chemist and radiochemist who is a professor of radiology, professor of pharmacology and professor of medicinal chemistry, as well as a core member of the Rogel Cancer Center at the University of Michigan in the United States. He is Chief of Nuclear Medicine and director of the University of Michigan Positron Emission Tomography (PET) Center, and runs a research group developing new radiochemistry methodology and novel PET radiotracers.

<span class="mw-page-title-main">Fluoroethyl fluoroacetate</span> Chemical compound

Fluoroethyl fluoroacetate, or more accurately 2-fluoroethyl fluoroacetate, is an organic compound with the chemical formula FCH2CO2CH2CH2F. It is the fluoroacetate ester of 2-fluoroethanol, or in other words, the 2-fluoroethyl ester of fluoroacetic acid. 2-Fluoroethyl fluoroacetate is two times more toxic than methyl fluoroacetate.

<span class="mw-page-title-main">Fluoroaspirin</span> Chemical compound

Fluoroaspirin is the fluoroacetate ester of salicylic acid. It is the fluoroacetate analog of aspirin. Like other fluoroacetate esters, fluoroaspirin is highly toxic.

4-Fluorobutanol is a chemical compound, a flammable colorless liquid which is a fluorinated alcohol. Like 2-fluoroethanol, it is highly toxic due to its ready metabolism to fluoroacetate.

<span class="mw-page-title-main">2-Ethylhexyl fluoroacetate</span> Chemical compound

2-Ethylhexyl fluoroacetate is an organic compound with the chemical formula FCH2CO2CH2CH(CH2CH3)CH2CH2CH2CH3. It is the fluoroacetate ester of 2-ethylhexanol, in other words, the 2-ethylhexyl ester of fluoroacetic acid. It can be produced by reaction of ethyl fluoroacetate with 2-ethylhexanol. 2-Ethylhexyl fluoroacetate is a liquid that is highly toxic by skin absorption.

References

  1. 1 2 3 4 5 6 Record of CAS RN 371-62-0 in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 18. February 2010.
  2. ↑ Gergel, Max G. (March 1977). Excuse me sir, would you like to buy a kilo of isopropyl bromide? (PDF). Pierce Chemical. p. 92, which also opines that "By the time you have established this [odor] you have probably had a fatal exposure, unless, like Max Gergel circa 1945—you have a hyperactive liver."
  3. ↑ "Ethylene fluorohydrin (CHEM004230)".
  4. ↑ Siegemund, Günter; Schwertfeger, Werner; Feiring, Andrew; Smart, Bruce; Behr, Fred; Vogel, Herward; McKusick, Blaine (2000). "Fluorine Compounds, Organic". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a11_349. ISBN   978-3527306732.
  5. ↑ Hoffmann, Friedrich W. (1948). "Preparation of Aliphatic Fluorides". Journal of the American Chemical Society. 70 (7): 2596–2597. doi:10.1021/ja01187a505. PMID   18875124.
  6. ↑ Shahak, Israel; Bergmann, Ernst D. (1965). "A convenient of synthesis β- and γ-fluoro-alcohols". Chem. Commun. (7): 122a. doi:10.1039/c1965000122a.
  7. ↑ Bhadury, Pinaki S.; Raza, Syed K.; Jaiswal, Devendra K. (1999). "A semi-molten mixture of hexadecyltributylphosphonium bromide and potassium fluoride in the synthesis of organofluorine compounds". Journal of Fluorine Chemistry. 99 (2): 115–117. doi:10.1016/s0022-1139(99)00121-9.
  8. ↑ Huang, Jinfan; Hedberg, Kenneth (1989). "Conformational analysis. 13. 2-Fluoroethanol. An investigation of the molecular structure and conformational composition at 20, 156, and 240.degree.. Estimate of the anti-gauche energy difference". Journal of the American Chemical Society. 111 (18): 6909–6913. doi:10.1021/ja00200a003.
  9. ↑ Dixon, David A.; Smart, Bruce E. (1991). "Conformational energies of 2-fluoroethanol and 2-fluoroacetaldehyde enol: Strength of the internal hydrogen bond". The Journal of Physical Chemistry. 95 (4): 1609–1612. doi:10.1021/j100157a020.
  10. ↑ Bronnert, D.L.E.; Saunders, B.C. (1960). "Toxic fluorine compounds containing the C—F link—XI". Tetrahedron. 10 (3–4): 160–163. doi:10.1016/s0040-4020(01)97802-0.
  11. 1 2 Falzon, C. L., Ackermann, U., Spratt, N., Tochon-Danguy, H. J., White, J., Howells, D., & Scott, A. M. (2006).F-18 labelledN,N-bis-haloethylamino-phenylsulfoxides — a new class of compounds for the imaging of hypoxic tissue. Journal of Labelled Compounds and Radiopharmaceuticals, 49(12), 1089–1103. https://doi.org/10.1002/jlcr.1129
  12. ↑ Pan, J., Pourghiasian, M., Hundal, N., Lau, J., Bénard, F., Dedhar, S., & Lin, K.-S. (2013). 2-[18F]-fluoroethanol and 3-[18F]-fluoropropanol: facile preparation, biodistribution in mice, and their application as nucleophiles in the synthesis of [18F]fluoroalkyl aryl ester and ether PET tracers. Nuclear Medicine and Biology, 40(6), 850–857. https://doi.org/10.1016/j.nucmedbio.2013.04.009
  13. 1 2 3 4 Treble D. H. (1962). The metabolism of 2-fluoroethanol. The Biochemical journal, 82(1), 129–134. https://doi.org/10.1042/bj0820129
  14. ↑ Goncharov, N. V., Jenkins, R. O., & Radilov, A. S. (2006). Toxicology of fluoroacetate: a review, with possible directions for therapy research. Journal of applied toxicology : JAT, 26(2), 148–161. https://doi.org/10.1002/jat.1118
  15. ↑ Timbrell, J. A. (2008). Principles of Biochemical Toxicology (Fourth Edition). Taylor & Francis. p. 358-359.
  16. ↑ Saunders, B. C., Stacey, G. J., & Wilding, I. G. E. (1948). Toxic Fluorine Compounds Containing the C-F Link. Part II. 2-Fluoroethanol and its Derivatives. University Chemical Laboratory Cambridge, 1. Retrieved from https://pubs-rsc-org.ru.idm.oclc.org/en/content/articlepdf/1949/jr/jr9490000773.
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