Silver trifluoromethanesulfonate: Difference between revisions

| 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

| 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 [[silver|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 [[Recrystallization (chemistry)|recrystallized]] from [[benzene]]/[[tetrachloromethane]] or [[Diethyl ether|ether]]/[[tetrachloromethane]] for purification.

In an improved version by George Whitesides, dilute TfOH is reacted with [[Silver oxide|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}}