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Cyanuric fluoride: Difference between revisions

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{{chembox {{chembox
| Watchedfields = changed
| verifiedrevid = 399735020 | verifiedrevid = 421445376
| ImageFile = Cyanuric fluoride.svg | ImageFileL1 = Cyanuric fluoride.svg
| ImageSize =
| 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 | IUPACName = 2,4,6-trifluoro-1,3,5-triazine
| OtherNames = trifluorotriazine,<br/> 2,4,6-trifluoro-s-triazine,<br/> cyanuryl fluoride embox | OtherNames = trifluorotriazine,<br/> 2,4,6-trifluoro-s-triazine,<br/> cyanuryl fluoride embox
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 12143 | ChemSpiderID = 12143
Line 13: Line 18:
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = VMKJWLXVLHBJNK-UHFFFAOYSA-N | StdInChIKey = VMKJWLXVLHBJNK-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 675-14-9 | CASNo = 675-14-9
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 31KW4S5FBB
| PubChem = 12664 | PubChem = 12664
| EC_number = 211-620-8
| UNNumber = 3389 1935
| SMILES = Fc1nc(F)nc(F)n1 | SMILES = Fc1nc(F)nc(F)n1
| InChI = 1/C3F3N3/c4-1-7-2(5)9-3(6)8-1 }} | InChI = 1/C3F3N3/c4-1-7-2(5)9-3(6)8-1 }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| Formula = C<sub>3</sub>F<sub>3</sub>N<sub>3</sub> | Formula = C<sub>3</sub>F<sub>3</sub>N<sub>3</sub>
| MolarMass = 135.047 g/mol | MolarMass = 135.047 g/mol
| Appearance = colourless liquid | Appearance = colourless liquid
| Density = 1.574 g/cm<sup>3</sup> | Density = 1.574 g/cm<sup>3</sup>
| MeltingPt = &minus;38 °C | MeltingPtC = -38
| BoilingPt = 74 °C | BoilingPtC = 74
| Solubility = }} | Solubility = }}
| Section3 = {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards = | MainHazards =
| RPhrases = {{R24}}, {{R26}}, {{R35}} | GHSPictograms = {{GHS05}}{{GHS06}}
| GHSSignalWord = Danger
| SPhrases = {{S26}}, {{S28}}, {{S36/37/39}}, {{S45}}
| HPhrases = {{H-phrases|310|314|330}}
| RSPhrases =
| 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 = | FlashPt =
| AutoignitionPt =
| Autoignition = }}
}}
| Section4 = {{Chembox Related |Section4={{Chembox Related
| OtherAnions = | OtherAnions =
| OtherCations = | OtherCations =
| OtherFunctn = | OtherFunction =
| OtherFunction_label =
| Function =
| OtherCpds = ], ]}} | OtherCompounds = ], ], ]}}
}} }}
'''Cyanuric fluoride''' or '''2,4,6-trifluoro-1,3,5-triazine''' is a ] with the ] (CNF)<sub>3</sub>. It is a '''Cyanuric fluoride''' or '''2,4,6-trifluoro-1,3,5-triazine''' is a ] with the ] (CNF)<sub>3</sub>. It is a
colourless, pungent liquid. It has been used as a precursor for ], as a specific reagent for ] residues in enzymes, and as a ] agent.<ref>{{cite encyclopedia | encyclopedia= Kirk-Othmer Encyclopedia of Chemical Technology |title= Fluorinated aromatic compounds |year= 1994 |publisher= Wiley-Interscience |volume= 11 |pages= 608}}</ref> colourless, pungent liquid. It has been used as a precursor for ], as a specific reagent for ] residues in enzymes, and as a ] agent.<ref>{{cite encyclopedia | encyclopedia= Kirk-Othmer Encyclopedia of Chemical Technology |title= Fluorinated aromatic compounds |year= 1994 |publisher= Wiley-Interscience |volume= 11 |pages= 608}}</ref>

It is classified as an ] in the United States as defined in Section 302 of the U.S. ] (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.<ref name="gov-right-know">{{Cite journal | publisher = ] | 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 }}</ref>


==Preparation and reactions== ==Preparation and reactions==


Cyanuric fluoride is prepared by fluorinating ]. The fluorinating agent may be SbF<sub>3</sub>Cl<sub>2</sub><ref>{{cite journal | author = Abe F. Maxwell, John S. Fry & Lucius A. Bigelow | year = 1958 | title = The Indirect Fluorination of Cyanuric Chloride | journal = Journal of American Chemical Society | volume = 80 | issue = 3 | pages = 548 | doi = 10.1021/ja01536a010 }}</ref>, KSO<sub>2</sub>F<ref name="grisley">{{cite journal | author = Daniel W. Grisley, Jr, E.&nbsp;W. Gluesenkamp & 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 | doi = 10.1021/jo01105a620 }}</ref>, or ]<ref>{{cite journal | author = C.&nbsp;W. Tullock & D.&nbsp;D. Coffman | year = 1960 | title = Synthesis of Fluorides by Metathesis with Sodium Fluoride | journal = Journal of Organic Chemistry | volume = 25 | issue = 11 | pages = 2016 Cyanuric fluoride is prepared by fluorinating ]. The fluorinating agent may be SbF<sub>3</sub>Cl<sub>2</sub>,<ref>{{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 }}</ref> KSO<sub>2</sub>F,<ref name="grisley">{{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 }}</ref> or ].<ref>{{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 }}</ref><ref>{{cite journal | author = Steffen Groß, Stephan Laabs, Andreas Scherrmann, Alexander Sudau, Nong Zhang & 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 | doi = 10.1002/1521-3897(200009)342:7<711::AID-PRAC711>3.0.CO;2-M }}</ref>. | doi = 10.1021/jo01081a050 }}</ref><ref>{{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 }}</ref>


Cyanuric fluoride is used for the mild and direct conversion of ]s to ]:<ref>{{cite journal | author = George A. Olah, Masatomo Nojima & Istvan Kerekes | year = 1973 | title = Synthetic Methods and Reactions; IV. Fluorination of Carboxylic Acids with Cyanuric Fluoride | journal = Synthesis | pages = 487 | issue = 08 | doi = 10.1055/s-1973-22238 | volume = 1973 }}</ref> Cyanuric fluoride is used for the mild and direct conversion of ]s to ]:<ref>{{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 }}</ref>


:] :]


Other fluorinating methods are less direct and may be incompatible with some ]s.<ref>{{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}}</ref> Other fluorinating methods are less direct and may be incompatible with some ]s.<ref>{{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 }}</ref>


Cyanuric fluoride ] easily to ] and it reacts more readily with ]s than cyanuric chloride.<ref name="grisley" /> ] of cyanuric fluoride at 1300&nbsp;°C is a way to prepare ]:<ref>{{cite journal | author = F.&nbsp;S. Fawcett & R.&nbsp;D. Lipscomb | year = 1964 | title = Cyanogen Fluoride: Synthesis and Properties | journal = Journal of American Chemical Society | volume = 86 | issue = 13 | pages = 2576 | doi = 10.1021/ja01067a011 }}</ref> Cyanuric fluoride ] easily to ] and it reacts more readily with ]s than cyanuric chloride.<ref name="grisley" /> ] of cyanuric fluoride at 1300&nbsp;°C is a way to prepare ]:<ref>{{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 }}</ref>
:(CNF)<sub>3</sub> &rarr; 3 CNF. :(CNF)<sub>3</sub> → 3 CNF.


==References== ==References==
<references/> <references/>


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