Cyanuric fluoride


Cyanuric fluoride
Cyanuric fluoride
Identifiers
CAS number 675-14-9
PubChem 12664
ChemSpider 12143 YesY
Jmol-3D images Image 1
Properties
Molecular formula C3F3N3
Molar mass 135.047 g/mol
Appearance colourless liquid
Density 1.574 g/cm3
Melting point

−38 °C

Boiling point

74 °C

Hazards
R-phrases R24, R26, R35
S-phrases S26, S28, S36/37/39, S45
Related compounds
Related compounds cyanuric acid, cyanuric chloride
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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]

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]

Fluorination with cyanuric fluoride.svg

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

  1. ^ "Fluorinated aromatic compounds". Kirk-Othmer Encyclopedia of Chemical Technology. 11. Wiley-Interscience. 1994. pp. 608. 
  2. ^ Abe F. Maxwell, John S. Fry & Lucius A. Bigelow (1958). "The Indirect Fluorination of Cyanuric Chloride". Journal of American Chemical Society 80 (3): 548. doi:10.1021/ja01536a010. 
  3. ^ 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. doi:10.1021/jo01105a620. 
  4. ^ C. W. Tullock & D. D. Coffman (1960). "Synthesis of Fluorides by Metathesis with Sodium Fluoride". Journal of Organic Chemistry 25 (11): 2016. doi:10.1021/jo01081a050. 
  5. ^ 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. doi:10.1002/1521-3897(200009)342:7<711::AID-PRAC711>3.0.CO;2-M. 
  6. ^ George A. Olah, Masatomo Nojima & Istvan Kerekes (1973). "Synthetic Methods and Reactions; IV. Fluorination of Carboxylic Acids with Cyanuric Fluoride". Synthesis 1973 (08): 487. doi:10.1055/s-1973-22238. 
  7. ^ Barda, David A. (2005). "Cyanuric Fluoride". Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons. pp. 77. doi:10.1002/047084289X.rn00043. 
  8. ^ F. S. Fawcett & R. D. Lipscomb (1964). "Cyanogen Fluoride: Synthesis and Properties". Journal of American Chemical Society 86 (13): 2576. doi:10.1021/ja01067a011. 

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