Cyanuric fluoride
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| UN number | 3389 1935 |
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| Template:Longitem | C3F3N3 |
| Molar mass | 135.047 g/mol |
| Appearance | colourless liquid |
| Density | 1.574 g/cm3 |
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| Template:Longitem | cyanuric acid, cyanuric chloride, cyanuric bromide |
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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
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