cyanuric fluoride
{{chembox
| Watchedfields = changed
| verifiedrevid = 421445376
| ImageFileL1 = Cyanuric fluoride.svg
| ImageSizeL1 = 120
| ImageAltL1 = Skeletal formula of cyanuric fluoride
| ImageFileR1 = Cyanuric-fluoride-3D-spacefill.png
| ImageSizeR1 = 130
| ImageAltR1 = Space-filling model of the cyanuric fluoride molecule
| IUPACName = 2,4,6-trifluoro-1,3,5-triazine
| OtherNames = trifluorotriazine,
2,4,6-trifluoro-s-triazine,
cyanuryl fluoride embox
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 12143
| InChIKey = VMKJWLXVLHBJNK-UHFFFAOYAH
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C3F3N3/c4-1-7-2(5)9-3(6)8-1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = VMKJWLXVLHBJNK-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 675-14-9
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 31KW4S5FBB
| PubChem = 12664
| EC_number = 211-620-8
| UNNumber = 3389 1935
| SMILES = Fc1nc(F)nc(F)n1
| InChI = 1/C3F3N3/c4-1-7-2(5)9-3(6)8-1 }}
|Section2={{Chembox Properties
| Formula = C3F3N3
| MolarMass = 135.047 g/mol
| Appearance = colourless liquid
| Density = 1.574 g/cm3
| MeltingPtC = -38
| BoilingPtC = 74
| Solubility = }}
|Section3={{Chembox Hazards
| MainHazards =
| GHSPictograms = {{GHS05}}{{GHS06}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|310|314|330}}
| PPhrases = {{P-phrases|260|262|264|270|271|280|284|301+330+331|302+350|303+361+353|304+340|305+351+338|310|320|321|322|361|363|403+233|405|501}}
| FlashPt =
| AutoignitionPt =
}}
|Section4={{Chembox Related
| OtherAnions =
| OtherCations =
| OtherFunction =
| OtherFunction_label =
| OtherCompounds = cyanuric acid, cyanuric chloride, cyanuric bromide}}
}}
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.{{cite encyclopedia | encyclopedia= Kirk-Othmer Encyclopedia of Chemical Technology |title= Fluorinated aromatic compounds |year= 1994 |publisher= Wiley-Interscience |volume= 11 |pages= 608}}
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.{{Cite journal | publisher = Government Printing Office | title = 40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities | url = http://edocket.access.gpo.gov/cfr_2008/julqtr/pdf/40cfr355AppA.pdf | edition = July 1, 2008 | access-date = October 29, 2011 | archive-url = https://web.archive.org/web/20120225051612/http://edocket.access.gpo.gov/cfr_2008/julqtr/pdf/40cfr355AppA.pdf | archive-date = February 25, 2012 | url-status = dead }}
Preparation and reactions
Cyanuric fluoride is prepared by fluorinating cyanuric chloride. The fluorinating agent may be SbF3Cl2,{{cite journal |author1=Abe F. Maxwell |author2=John S. Fry |author3=Lucius A. Bigelow | year = 1958 | title = The Indirect Fluorination of Cyanuric Chloride | journal = Journal of the American Chemical Society | volume = 80 | issue = 3 | pages = 548–549 | doi = 10.1021/ja01536a010 }} KSO2F,{{cite journal |author1=Daniel W. Grisley, Jr |author2=E. W. Gluesenkamp |author3=S. Allen Heininger | year = 1958 | title = Reactions of Nucleophilic Reagents with Cyanuric Fluoride and Cyanuric Chloride | journal = Journal of Organic Chemistry | volume = 23 | issue = 11 | pages = 1802–1804 | doi = 10.1021/jo01105a620 }} or NaF.{{cite journal |author1=C. W. Tullock |author2=D. D. Coffman | year = 1960 | title = Synthesis of Fluorides by Metathesis with Sodium Fluoride | journal = Journal of Organic Chemistry | volume = 25 | issue = 11 | pages = 2016–2019
Cyanuric fluoride is used for the mild and direct conversion of carboxylic acids to acyl fluorides:{{cite journal |author1=George A. Olah |author2=Masatomo Nojima |author3=Istvan Kerekes | year = 1973 | title = Synthetic Methods and Reactions; IV. Fluorination of Carboxylic Acids with Cyanuric Fluoride | journal = Synthesis | pages = 487–488 | issue = 8 | doi = 10.1055/s-1973-22238 | volume = 1973 }}
Other fluorinating methods are less direct and may be incompatible with some functional groups.{{cite encyclopedia | encyclopedia= Encyclopedia of Reagents for Organic Synthesis | last1= Barda | first1= David A. |title= Cyanuric Fluoride |year= 2005 |publisher= John Wiley & Sons |pages= 77 | doi = 10.1002/047084289X.rn00043| isbn= 0471936235 }}
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:{{cite journal |author1=F. S. Fawcett |author2=R. D. Lipscomb | year = 1964 | title = Cyanogen Fluoride: Synthesis and Properties | journal = Journal of the American Chemical Society | volume = 86 | issue = 13 | pages = 2576–2579 | doi = 10.1021/ja01067a011 }}
:(CNF)3 → 3 CNF.