2-Fluoroethanol

changed changed 477213382 2-Fluoroethanol.svg 120px 2-fluoroethanol-from-xtal-3D-bs-17.png 120px 2-fluoroethanol-from-xtal-3D-sf.png 120px 2-Fluoroethan-1-ol Ethylene fluorohydrine correct chemspider 9354 1/C2H5FO/c3-1-2-4/h4H,1-2H2 GGDYAKVUZMZKRV-UHFFFAOYAT FCCO correct EBI 115586 correct chemspider 1S/C2H5FO/c3-1-2-4/h4H,1-2H2 correct chemspider GGDYAKVUZMZKRV-UHFFFAOYSA-N correct CAS 371-62-0 correct FDA 4M427A5HML 9737 2 5 1 1 1.1040 g cm−3490201 371-62-0 18. February 2010 −26.3 103.5 miscible 19 mbar (15 °C) 14.74 (predicted) https://contaminantdb.ca/contaminants/CHEM004230 Ethylene fluorohydrin (CHEM004230) Musky, rather tartExcuse me sir, would you like to buy a kilo of isopropyl bromide? Max G. Gergel Max Gergel March 1977 Pierce Chemical 92 none, 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." Soluble in ethanol, ethyl ether, acetone 4 2 1 skull and crossbones flame 226 300+310+330 210 233 240 241 242 243 260 262 264 270 271 280 284 301+310+330 303+361+353 304+340+310 363 370+378 403+233 403+235 405 501 34 °C (93.2 °F; 307.15 K) 2-Chloroethanol 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.10.1002/14356007.a11_349 Fluorine Compounds, Organic 2000 Siegemund Günter Schwertfeger Werner Feiring Andrew Smart Bruce Behr Fred Vogel Herward McKusick Blaine 3527306730 Synthesis 2-Fluoroethanol was originally synthesized by treating 2-chloroethanol with potassium fluoride, in a simple Finkelstein reaction.10.1021/ja01187a505 Preparation of Aliphatic Fluorides 1948 Hoffmann Friedrich W. Journal of the American Chemical Society 70 7 2596–2597 18875124 1948JAChS..70.2596H 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-one10.1039/c1965000122a A convenient of synthesis β- and γ-fluoro-alcohols 1965 Shahak Israel Bergmann Ernst D. Chem. Commun. 7 122a and from 2-bromoethanol.10.1016/s0022-1139(99)00121-9 A semi-molten mixture of hexadecyltributylphosphonium bromide and potassium fluoride in the synthesis of organofluorine compounds 1999 Bhadury Pinaki S. Raza Syed K. Jaiswal Devendra K. Journal of Fluorine Chemistry 99 2 115–117 1999JFluC..99..115B Structure and reactivity Hydrogen bonding stabilizes the gauche conformer.10.1021/ja00200a003 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 1989 Huang Jinfan Hedberg Kenneth Journal of the American Chemical Society 111 18 6909–6913 1989JAChS.111.6909H 10.1021/j100157a020 Conformational energies of 2-fluoroethanol and 2-fluoroacetaldehyde enol: Strength of the internal hydrogen bond 1991 Dixon David A. Smart Bruce E. The Journal of Physical Chemistry 95 4 1609–1612 In a basic solution, 2-fluoroethanol undergoes dehydrofluorination, giving acetaldehyde.10.1016/s0040-4020(01)97802-0 Toxic fluorine compounds containing the C—F link—XI 1960 Bronnert D.L.E. Saunders B.C. Tetrahedron 10 3–4 160–163 Reaction of 2-fluoroethanol with trifluoromethanesulfonic anhydride in the presence of base gives the triflate ester. 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.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.2013.04.009Falzon, 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 Metabolism It was patented as a rodenticide in Germany in 1935.Treble D. H. (1962). The metabolism of 2-fluoroethanol. The Biochemical journal, 82(1), 129–134. https://doi.org/10.1042/bj0820129 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. 2-Fluoroethanol is converted by alcohol dehydrogenase (ADH) using nicotinamide adenine dinucleotide (NAD+) as cofactor, ultimately leading to the formation of fluoroacetaldehyde and then fluoroacetate. Fluoroacetate is a precursor to fluorocitrate,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 an inhibitor of aconitase, an enzyme that participates in the TCA cycle.Timbrell, J. A. (2008). Principles of Biochemical Toxicology (Fourth Edition). Taylor & Francis. p. 358-359. 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.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. 2-Fluoroethanol is also toxic to other animals with LD50 ranging from 7 to 1500 mg/kg bodyweight. See also Sodium fluoroacetate 1,3-Difluoro-2-propanol 4-Fluorobutanol References Category:Rodenticides Category:Primary alcohols Category:Organofluorides Category:Fluoroethyl compounds Category:Organic compounds with 2 carbon atoms Category:Fluoroethanols