Tetramethylammonium fluoride is the quaternary ammonium salt with the formula (CH3)4NF. This hygroscopic white solid is a source of “naked fluoride": fluoride ions not complexed with a metal atom. Most other soluble salts of fluoride are in fact bifluorides, HF2–. Historically, there have been two main approaches to prepare tetramethylammonium fluoride: hydrofluoric acid neutralization of tetramethylammonium hydroxide, and salt metathesis between different ammonium salts and inorganic fluoride sources, such as KF or CsF.[1] Because the fluoride anion is extremely basic, the salt slowly reacts with acetonitrile, inducing dimerization to CH3C(NH2)=CHCN, which co-crystallizes.[2]
Tetramethylphosphonium fluoride (CH3)4PF forms stable acetonitrile solutions. It is prepared from the ylide and potassium bifluoride:
(CH3)3P=CH2 + KHF2 → (CH3)4PF + KF
Gaseous tetramethylphosphonium fluoride exists as the phosphorane but autoionizes in acetonitrile solution.[3] A more elaborate phosphazenium salt ([(CH3)2N)3P]2N+F−) is also known.[4]
^Iashin, Vladimir; Wirtanen, Tom; Perea-Buceta, Jesus E. (2022-02-18). "Tetramethylammonium Fluoride: Fundamental Properties and Applications in C-F Bond-Forming Reactions and as a Base". Catalysts. 12 (2): 233. doi:10.3390/catal12020233. hdl:10138/340938. ISSN 2073-4344.
^Christe, K. O.; Wilson, W. W.; Wilson, R. D.; Bau, R.; Feng, J. A. (1990). "Syntheses, Properties, and Structures of Anhydrous Tetramethylammonium Fluoride and Its 1:1 Adduct with trans-3-Amino-2-butenenitrile". Journal of the American Chemical Society. 112 (21): 7619–7625. doi:10.1021/ja00177a025.
^Kornath, Andreas; Neumann, F.; Oberhammer, H. (2003). "Tetramethylphosphonium Fluoride: "Naked" Fluoride and Phosphorane". Inorganic Chemistry. 42 (9): 2894–2901. doi:10.1021/ic020663c. PMID 12716181.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^Schwesinger, Reinhard (2001). "1,1,1,3,3,3-Hexakis(dimethylamino)-1λ5,3λ5-diphosphazenium Fluoride". e-EROS Encyclopedia of Reagents for Organic Synthesis. pp. 1–2. doi:10.1002/047084289X.rh014m. ISBN0471936235.
tetramethylammonium, fluoride, tetramethyl, ammonium, fluoride, quaternary, ammonium, salt, with, formula, this, hygroscopic, white, solid, source, naked, fluoride, fluoride, ions, complexed, with, metal, atom, most, other, soluble, salts, fluoride, fact, bifl. Tetramethyl ammonium fluoride is the quaternary ammonium salt with the formula CH3 4NF This hygroscopic white solid is a source of naked fluoride fluoride ions not complexed with a metal atom Most other soluble salts of fluoride are in fact bifluorides HF2 Historically there have been two main approaches to prepare tetramethyl ammonium fluoride hydrofluoric acid neutralization of tetramethyl ammonium hydroxide and salt metathesis between different ammonium salts and inorganic fluoride sources such as KF or CsF 1 Because the fluoride anion is extremely basic the salt slowly reacts with acetonitrile inducing dimerization to CH3C NH2 CHCN which co crystallizes 2 Tetramethylammonium fluoride Names Preferred IUPAC name N N N Trimethylmethanaminium fluoride Identifiers CAS Number 373 68 2 3D model JSmol Interactive image ChemSpider 61120 ECHA InfoCard 100 006 154 EC Number 206 769 0 PubChem CID 67803 CompTox Dashboard EPA DTXSID40883374 InChI InChI 1S C4H12N FH c1 5 2 3 4 h1 4H3 1H q 1 p 1Key GTDKXDWWMOMSFL UHFFFAOYSA M SMILES C N C C C F Properties Chemical formula C 4H 12F N Molar mass 93 145 g mol 1 Appearance white solid Hazards GHS labelling Pictograms Signal word Warning Hazard statements H302 H312 H315 H319 H332 H335 Precautionary statements P261 P264 P270 P271 P280 P301 P312 P302 P352 P304 P312 P304 P340 P305 P351 P338 P312 P321 P322 P330 P332 P313 P337 P313 P362 P363 P403 P233 P405 P501 Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox referencesRelated salts editTetramethyl phosphonium fluoride CH3 4PF forms stable acetonitrile solutions It is prepared from the ylide and potassium bifluoride CH3 3P CH2 KHF2 CH3 4PF KF Gaseous tetramethylphosphonium fluoride exists as the phosphorane but autoionizes in acetonitrile solution 3 A more elaborate phosphazenium salt CH3 2N 3P 2N F is also known 4 Anhydrous Tetrabutylammonium fluoride has been prepared by the reaction of hexafluorobenzene and tetrabutylammonium cyanide 5 References edit Iashin Vladimir Wirtanen Tom Perea Buceta Jesus E 2022 02 18 Tetramethylammonium Fluoride Fundamental Properties and Applications in C F Bond Forming Reactions and as a Base Catalysts 12 2 233 doi 10 3390 catal12020233 hdl 10138 340938 ISSN 2073 4344 Christe K O Wilson W W Wilson R D Bau R Feng J A 1990 Syntheses Properties and Structures of Anhydrous Tetramethylammonium Fluoride and Its 1 1 Adduct with trans 3 Amino 2 butenenitrile Journal of the American Chemical Society 112 21 7619 7625 doi 10 1021 ja00177a025 Kornath Andreas Neumann F Oberhammer H 2003 Tetramethylphosphonium Fluoride Naked Fluoride and Phosphorane Inorganic Chemistry 42 9 2894 2901 doi 10 1021 ic020663c PMID 12716181 a href Template Cite journal html title Template Cite journal cite journal a CS1 maint multiple names authors list link Schwesinger Reinhard 2001 1 1 1 3 3 3 Hexakis dimethylamino 1l5 3l5 diphosphazenium Fluoride e EROS Encyclopedia of Reagents for Organic Synthesis pp 1 2 doi 10 1002 047084289X rh014m ISBN 0471936235 Haoran Sun amp Stephen G DiMagno 2005 Anhydrous Tetrabutylammonium Fluoride Journal of the American Chemical Society 127 7 2050 1 doi 10 1021 ja0440497 PMID 15713075 Retrieved from https en wikipedia org w index php title Tetramethylammonium fluoride amp oldid 1193568676, wikipedia, wiki, book, books, library,
