Cyanuric fluoride

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 Edit this at Wikidata
EC Number
  • 211-620-8
UNII
UN number 3389 1935
  • InChI=1S/C3F3N3/c4-1-7-2(5)9-3(6)8-1 checkY
    Key: VMKJWLXVLHBJNK-UHFFFAOYSA-N checkY
  • InChI=1/C3F3N3/c4-1-7-2(5)9-3(6)8-1
    Key: VMKJWLXVLHBJNK-UHFFFAOYAH
  • Fc1nc(F)nc(F)n1
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
GHS labelling:
GHS05: CorrosiveGHS06: Toxic
Danger
H310, H314, H330
P260, P262, P264, P270, P271, P280, P284, P301+P330+P331, P302+P350, P303+P361+P353, P304+P340, P305+P351+P338, P310, P320, P321, P322, P361, P363, P403+P233, P405, P501
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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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

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]

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

  1. ^ "Fluorinated aromatic compounds". Kirk-Othmer Encyclopedia of Chemical Technology. Vol. 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. Archived from the original (PDF) on February 25, 2012. Retrieved October 29, 2011. {{cite journal}}: Cite journal requires |journal= (help)
  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 (8): 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. ISBN 0471936235.
  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.