Cyanuric fluoride

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Cyanuric fluoride
Skeletal formula of cyanuric fluoride
Space-filling model of the cyanuric fluoride molecule
Names
IUPAC name
2,4,6-trifluoro-1,3,5-triazine
Other names
trifluorotriazine,
2,4,6-trifluoro-s-triazine,
cyanuryl fluoride embox
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.010.565
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)
Hazards
R-phrases (outdated) R24, R26, R35
S-phrases (outdated) S26, S28, S36/37/39, S45
Related compounds
Related compounds
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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Infobox references

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]

It is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.[2]

Preparation and reactions[edit]

Cyanuric fluoride is prepared by fluorinating cyanuric chloride. The fluorinating agent may be SbF3Cl2,[3] KSO2F,[4] or NaF.[5][6]

Cyanuric fluoride is used for the mild and direct conversion of carboxylic acids to acyl fluorides:[7]

Fluorination with cyanuric fluoride.svg

Other fluorinating methods are less direct and may be incompatible with some functional groups.[8]

Cyanuric fluoride hydrolyses easily to cyanuric acid and it reacts more readily with nucleophiles than cyanuric chloride.[4] Pyrolysis of cyanuric fluoride at 1300 °C is a way to prepare cyanogen fluoride:[9]

(CNF)3 → 3 CNF.

References[edit]

  1. ^ "Fluorinated aromatic compounds". Kirk-Othmer Encyclopedia of Chemical Technology. 11. Wiley-Interscience. 1994. p. 608. 
  2. ^ "40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities" (PDF) (July 1, 2008 ed.). Government Printing Office. Retrieved October 29, 2011. 
  3. ^ 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. 
  4. ^ 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. 
  5. ^ 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. 
  6. ^ 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. 
  7. ^ 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. 
  8. ^ Barda, David A. (2005). "Cyanuric Fluoride". Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons. p. 77. doi:10.1002/047084289X.rn00043. 
  9. ^ 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.