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Cyanuric fluoride - Wikipedia

From Wikipedia, the free encyclopedia

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^Y

3D model (JSmol)

Interactive image

ChemSpider

12143^Y

ECHA InfoCard

100.010.565

EC Number

211-620-8

PubChem CID

12664

UNII

31KW4S5FBB^Y

UN number

3389 1935

CompTox Dashboard (EPA)

DTXSID6060975

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)

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

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.^[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.
^ ^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): 1802–1804. 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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