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
CAS Number	675-14-9 Y
ChemSpider	12143 Y
Jmol 3D model	Interactive image
PubChem	12664
InChI 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
SMILES Fc1nc(F)nc(F)n1
Properties
Chemical formula	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)
Vapor pressure	{{{value}}}
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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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.

Preparation and reactions

Cyanuric fluoride is prepared by fluorinating cyanuric chloride. The fluorinating agent may be SbF₃Cl₂, KSO₂F, or NaF.

Cyanuric fluoride is used for the mild and direct conversion of carboxylic acids to acyl fluorides:

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Other fluorinating methods are less direct and may be incompatible with some functional groups.

Cyanuric fluoride hydrolyses easily to cyanuric acid and it reacts more readily with nucleophiles than cyanuric chloride. Pyrolysis of cyanuric fluoride at 1300 °C is a way to prepare cyanogen fluoride:

(CNF)₃ → 3 CNF.