Cyanuric fluoride

Cyanuric fluoride
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 ;
3D model (JSmol)	Interactive image;
ChemSpider	12143 ;
ECHA InfoCard	100.010.565
EC Number	211-620-8;
PubChem CID	12664;
UNII	31KW4S5FBB ;
UN number	3389 1935
CompTox Dashboard (EPA)	DTXSID6060975 ;
	InChI InChI=1S/C3F3N3/c4-1-7-2(5)9-3(6)8-1 Key: VMKJWLXVLHBJNK-UHFFFAOYSA-N ; 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)
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H310, H314, H330
Precautionary statements	P260, P262, P264, P270, P271, P280, P284, P301+P330+P331, P302+P350, P303+P361+P353, P304+P340, P305+P351+P338, P310, P320, P321, P322, P361, P363, P403+P233, P405, P501
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). verify (what is ?) 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]

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

"Fluorinated aromatic compounds". Kirk-Othmer Encyclopedia of Chemical Technology. Vol. 11. Wiley-Interscience. 1994. p. 608.
"40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities" (PDF) (July 1, 2008 ed.). Government Printing Office. Archived from the original (PDF) on February 25, 2012. Retrieved October 29, 2011. {{cite journal}}: Cite journal requires |journal= (help)
Abe F. Maxwell; John S. Fry; Lucius A. Bigelow (1958). "The Indirect Fluorination of Cyanuric Chloride". Journal of the American Chemical Society. 80 (3): 548–549. doi:10.1021/ja01536a010.
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): 1802–1804. 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): 2016–2019. 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): 711–714. 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 (8): 487–488. doi:10.1055/s-1973-22238.
Barda, David A. (2005). "Cyanuric Fluoride". Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons. p. 77. doi:10.1002/047084289X.rn00043. ISBN 0471936235.
F. S. Fawcett; R. D. Lipscomb (1964). "Cyanogen Fluoride: Synthesis and Properties". Journal of the American Chemical Society. 86 (13): 2576–2579. doi:10.1021/ja01067a011.

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[1] "Fluorinated aromatic compounds". Kirk-Othmer Encyclopedia of Chemical Technology. Vol. 11. Wiley-Interscience. 1994. p. 608.

[gov-right-know-2] "40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities" (PDF) (July 1, 2008 ed.). Government Printing Office. Archived from the original (PDF) on February 25, 2012. Retrieved October 29, 2011. {{cite journal}}: Cite journal requires |journal= (help)

[3] Abe F. Maxwell; John S. Fry; Lucius A. Bigelow (1958). "The Indirect Fluorination of Cyanuric Chloride". Journal of the American Chemical Society. 80 (3): 548–549. doi:10.1021/ja01536a010.

[grisley-4] 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): 1802–1804. doi:10.1021/jo01105a620.

[5] C. W. Tullock; D. D. Coffman (1960). "Synthesis of Fluorides by Metathesis with Sodium Fluoride". Journal of Organic Chemistry. 25 (11): 2016–2019. doi:10.1021/jo01081a050.

[6] 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): 711–714. doi:10.1002/1521-3897(200009)342:7<711::AID-PRAC711>3.0.CO;2-M.

[7] George A. Olah; Masatomo Nojima; Istvan Kerekes (1973). "Synthetic Methods and Reactions; IV. Fluorination of Carboxylic Acids with Cyanuric Fluoride". Synthesis. 1973 (8): 487–488. doi:10.1055/s-1973-22238.

[8] Barda, David A. (2005). "Cyanuric Fluoride". Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons. p. 77. doi:10.1002/047084289X.rn00043. ISBN 0471936235.

[9] F. S. Fawcett; R. D. Lipscomb (1964). "Cyanogen Fluoride: Synthesis and Properties". Journal of the American Chemical Society. 86 (13): 2576–2579. doi:10.1021/ja01067a011.