Cyanuric fluoride
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| 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 |
| SMILES | Fc1nc(F)nc(F)n1 |
| InChI | 1/C3F3N3/c4-1-7-2(5)9-3(6)8-1 |
| InChI 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 |
| 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). [Expression error: Missing operand for > "The Indirect Fluorination of Cyanuric Chloride"]. Journal of American Chemical Society 80 (3): 548. doi:.
- ^ a b Daniel W. Grisley, Jr, E. W. Gluesenkamp & S. Allen Heininger (1958). [Expression error: Missing operand for > "Reactions of Nucleophilic Reagents with Cyanuric Fluoride and Cyanuric Chloride"]. Journal of Organic Chemistry 23 (11): 1802. doi:.
- ^ C. W. Tullock & D. D. Coffman (1960). [Expression error: Missing operand for > "Synthesis of Fluorides by Metathesis with Sodium Fluoride"]. Journal of Organic Chemistry 25 (11): 2016. doi:.
- ^ Steffen Groß, Stephan Laabs, Andreas Scherrmann, Alexander Sudau, Nong Zhang & Udo Nubbemeyer (2000). [Expression error: Missing operand for > "Improved Syntheses of Cyanuric Fluoride and Carboxylic Acid Fluorides"]. Journal für praktische Chemie 342 (7): 711. doi:.
- ^ George A. Olah, Masatomo Nojima & Istvan Kerekes (1973). [Expression error: Missing operand for > "Synthetic Methods and Reactions; IV. Fluorination of Carboxylic Acids with Cyanuric Fluoride"]. Synthesis 1973: 487. doi:.
- ^ "Cyanuric Fluoride". Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons. 2005. pp. 77. doi:.
- ^ F. S. Fawcett & R. D. Lipscomb (1964). [Expression error: Missing operand for > "Cyanogen Fluoride: Synthesis and Properties"]. Journal of American Chemical Society 86 (13): 2576. doi:.
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