Cyanuric fluoride
| Cyanuric fluoride |
|
2,4,6-trifluoro-1,3,5-triazine
|
Other names
trifluorotriazine,
2,4,6-trifluoro-s-triazine,
cyanuryl fluoride embox
|
| Identifiers |
| CAS number |
675-14-9 |
| PubChem |
12664 |
| ChemSpider |
12143 Y |
| Jmol-3D images |
Image 1 |
|
|
-
InChI=1S/C3F3N3/c4-1-7-2(5)9-3(6)8-1 Y
Key: VMKJWLXVLHBJNK-UHFFFAOYSA-N Y
InChI=1/C3F3N3/c4-1-7-2(5)9-3(6)8-1
Key: VMKJWLXVLHBJNK-UHFFFAOYAH
|
| 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 |
Y (verify) (what is: Y/N?)
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]
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. 11. Wiley-Interscience. 1994. pp. 608.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ Barda, David A. (2005). "Cyanuric Fluoride". Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons. pp. 77. doi:10.1002/047084289X.rn00043.
- ^ F. S. Fawcett & R. D. Lipscomb (1964). "Cyanogen Fluoride: Synthesis and Properties". Journal of American Chemical Society 86 (13): 2576. doi:10.1021/ja01067a011.