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

| doi = 10.1021/jo01081a050 }}{{cite journal |author1=Steffen Groß |author2=Stephan Laabs |author3=Andreas Scherrmann |author4=Alexander Sudau |author5=Nong Zhang |author6=Udo Nubbemeyer | year = 2000 | title = Improved Syntheses of Cyanuric Fluoride and Carboxylic Acid Fluorides | journal = Journal für Praktische Chemie | volume = 342 | issue = 7 | pages = 711–714 | doi = 10.1002/1521-3897(200009)342:7<711::AID-PRAC711>3.0.CO;2-M }}

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 }}

:450px

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.

References