Cyanuric fluoride
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| Names | |||
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| IUPAC name
2,4,6-trifluoro-1,3,5-triazine
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| Other names
trifluorotriazine,
2,4,6-trifluoro-s-triazine, cyanuryl fluoride embox | |||
| Identifiers | |||
3D model (JSmol)
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| ChemSpider | |||
| ECHA InfoCard | 100.010.565 | ||
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |||
| C3F3N3 | |||
| Molar mass | 135.047 g/mol | ||
| Appearance | colourless liquid | ||
| Density | 1.574 g/cm3 | ||
| Melting point | −38 °C (−36 °F; 235 K) | ||
| Boiling point | 74 °C (165 °F; 347 K) | ||
| Related compounds | |||
Related compounds
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cyanuric acid, cyanuric chloride, cyanuric bromide | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Cyanuric fluoride or 2,4,6-trifluoro-1,3,5-triazine is a chemical compound with the formula (CNF)3. It is a colourless, pungent liquid. It has been used as a precursor for fibre-reactive dyes, as a specific reagent for tyrosine residues in enzymes, and as a fluorinating agent.[1]
Preparation and reactions
Cyanuric fluoride is prepared by fluorinating cyanuric chloride. The fluorinating agent may be SbF3Cl2,[2] KSO2F,[3] or NaF.[4][5]
Cyanuric fluoride is used for the mild and direct conversion of carboxylic acids to acyl fluorides:[6]
Other fluorinating methods are less direct and may be incompatible with some functional groups.[7]
Cyanuric fluoride hydrolyses easily to cyanuric acid and it reacts more readily with nucleophiles than cyanuric chloride.[3] Pyrolysis of cyanuric fluoride at 1300 °C is a way to prepare cyanogen fluoride:[8]
- (CNF)3 → 3 CNF.
References
- ^ "Fluorinated aromatic compounds". Kirk-Othmer Encyclopedia of Chemical Technology. Vol. 11. Wiley-Interscience. 1994. p. 608.
- ^ Abe F. Maxwell, John S. Fry & Lucius A. Bigelow (1958). "The Indirect Fluorination of Cyanuric Chloride". Journal of the American Chemical Society. 80 (3): 548–549. doi:10.1021/ja01536a010.
- ^ a b Daniel W. Grisley, Jr, E. W. Gluesenkamp & S. Allen Heininger (1958). "Reactions of Nucleophilic Reagents with Cyanuric Fluoride and Cyanuric Chloride". Journal of Organic Chemistry. 23 (11): 1802–1804. doi:10.1021/jo01105a620.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - ^ C. W. Tullock & D. D. Coffman (1960). "Synthesis of Fluorides by Metathesis with Sodium Fluoride". Journal of Organic Chemistry. 25 (11): 2016–2019. doi:10.1021/jo01081a050.
- ^ Steffen Groß, Stephan Laabs, Andreas Scherrmann, Alexander Sudau, Nong Zhang & Udo Nubbemeyer (2000). "Improved Syntheses of Cyanuric Fluoride and Carboxylic Acid Fluorides". Journal für Praktische Chemie. 342 (7): 711–714. doi:10.1002/1521-3897(200009)342:7<711::AID-PRAC711>3.0.CO;2-M.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - ^ George A. Olah, Masatomo Nojima & Istvan Kerekes (1973). "Synthetic Methods and Reactions; IV. Fluorination of Carboxylic Acids with Cyanuric Fluoride". Synthesis. 1973 (08): 487–488. doi:10.1055/s-1973-22238.
- ^ Barda, David A. (2005). "Cyanuric Fluoride". Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons. p. 77. doi:10.1002/047084289X.rn00043.
- ^ F. S. Fawcett & R. D. Lipscomb (1964). "Cyanogen Fluoride: Synthesis and Properties". Journal of the American Chemical Society. 86 (13): 2576–2579. doi:10.1021/ja01067a011.