Silver trifluoromethanesulfonate

{{chembox | Watchedfields = changed | verifiedrevid = 440484526 | Name = | ImageFile = silver triflate.png | ImageFile1 = Silver-triflate-3D-vdW.png | IUPACName = silver trifluoromethanesulfonate | OtherNames = Silver triflate | SystematicName = | Section1 = {{Chembox Identifiers | CASNo_Ref = changed | CASNo=2923-28-6 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = UK2MGY9YSF | Abbreviations = AgOTf | ChemSpiderID = 68705 | EINECS = 220-882-2 | PubChem=76223 | StdInChI=1S/CHF3O3S.Ag/c2-1(3,4)8(5,6)7;/h(H,5,6,7);/q;+1/p-1 | StdInChIKey = QRUBYZBWAOOHSV-UHFFFAOYSA-M | SMILES=C(F)(F)(F)S(=O)(=O)[O-].[Ag+] }} | Section2 = {{Chembox Properties | Formula=CF₃SO₃Ag | MolarMass=256.937 g/mol | Appearance= | Odor = odorless | Density= | MeltingPtC= 286 | BoilingPtC= | Solubility= soluble }} | Section3 = {{Chembox Hazards | ExternalSDS = [http://msds.chem.ox.ac.uk/SI/silver_trifluoromethanesulfonate.html Oxford MSDS] | GHS_ref=<ref>{{cite web |title=Silver trifluoromethanesulfonate |url=https://pubchem.ncbi.nlm.nih.gov/compound/76223#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |access-date=15 December 2021 |language=en}}</ref> | GHSPictograms = {{GHS05}}{{GHS07}} | GHSSignalWord = Danger | HPhrases = {{H-phrases|315|319|335}} | PPhrases = {{P-phrases|260|261|264|271|280|301+330+331|302+352|303+361+353|304+340|305+351+338|310|312|321|332+313|337+313|362|363|403+233|405|501}} | NFPA-H = 1 | NFPA-F = 0 | NFPA-R = 0 | FlashPt= | AutoignitionPt = }} | Section4 = | Section5 = | Section6 = }}

'''Silver trifluoromethanesulfonate''', or '''silver triflate''' is the triflate (CF₃SO₃⁻) salt of Ag⁺. It is a white or colorless solid that is soluble in water and some organic solvents including, benzene. It is a reagent used in the synthesis of organic and inorganic triflates.

==Synthesis== An early preparation method starts from the barium salt of trifluoromethanesulfonic acid (TfOH), from which the free TfOH is formed with dilute sulfuric acid, which is then neutralized with silver carbonate (Ag₂CO₃).<ref name="Haszeldine">{{citation|surname1=R.N. Haszeldine, J.M. Kidd|periodical=J. Chem. Soc.|title=Perfluoroalkyl derivatives of sulphur. Part I. Trifluoromethanesulphonic acid|pages=4228–4232|date=1954|language=German|doi=10.1039/JR9540004228}}</ref><ref name="Gramstad">{{citation|surname1=T. Gramstadt, R.N. Haszeldine|periodical=J. Chem. Soc.|title=33. Perfluoroalkyl derivatives of sulphur. Part IV. Perfluoroalkanesulphonic acids|pages=173–180|date=1956|language=German|doi=10.1039/JR9560000173}}</ref>

:<chem>Ba^2+[{^-}OSO2CF3]2 ->[\ce{H2SO4}][-\ce{BaSO4}] CF3SO2OH ->[\ce{Ag2CO3}] CF3SO2O^- Ag+</chem>

The silver triflate is thereby obtained in a yield of 95% and can be recrystallized from benzene/tetrachloromethane or ether/tetrachloromethane for purification.

In an improved version by George Whitesides, dilute TfOH is reacted with silver(I)oxide (Ag₂O), which produces AgOTf in 98% yield.<ref name="Whitesides">{{citation |title=Reaction of α, ω-di-Grignard reagents with silver(I) salts form carbocyclic rings |date=1976 |periodical=J. Org. Chem. |volume=41 |issue=17 |pages=2882–2885 |doi=10.1021/jo00879a019 |surname1=G.M. Whitesides, F.D. Gutowski}}</ref>

==Reactions== It is used to prepare alkyl triflates from alkyl halides:<ref name=Stang>{{cite journal|last1=Stang|first1=Peter J.|last2=Hanack|first2=Michael|last3=Subramanian|first3=L. R.|title=Perfluoroalkanesulfonic Esters: Methods of Preparation and Applications in Organic Chemistry|journal=Synthesis|volume=1982|issue=2|year=1982|pages=85–126|issn=0039-7881|doi=10.1055/s-1982-29711|s2cid=94894040 }}</ref> :CF₃SO₂OAg + RX → CF₃SO₂OR + AgX (X = iodide usually)

In coordination chemistry, the salt is also useful to replace halide ligands with the more labile triflate ligand. For example, bromopentacarbonylrhenium can be converted to the more labile derivative using silver triflate:<ref>{{cite book|chapter=Manganese(I) and Rhenium(I) Pentacarbonyl(Trifluoromethanesulfonato) Complexes|year=1989|volume=26|author=Steven P. Schmidt |author2=Jay Nitschke |author3=William C. Trogler |title=Inorganic Syntheses|pages=113–117|doi=10.1002/9780470132579.ch20|isbn=978-0-470-13257-9}}</ref> :CF₃SO₂OAg + BrRe(CO)₅ → CF₃SO₂ORe(CO)₅ + AgBr

==References== {{Reflist}}

{{silver compounds}}

Category:Silver compounds Category:Triflates