Silver trifluoromethanesulfonate

Silver trifluoromethanesulfonate
Names
	IUPAC name silver trifluoromethanesulfonate
	Other names Silver triflate
Identifiers
CAS Number	2923-28-6changed;
3D model (JSmol)	Interactive image;
Abbreviations	AgOTf
ChemSpider	68705;
ECHA InfoCard	100.018.985
EC Number	220-882-2;
PubChem CID	76223;
UNII	UK2MGY9YSF ;
CompTox Dashboard (EPA)	DTXSID5062716 ;
	InChI InChI=1S/CHF3O3S.Ag/c2-1(3,4)8(5,6)7;/h(H,5,6,7);/q;+1/p-1 Key: QRUBYZBWAOOHSV-UHFFFAOYSA-M;
	SMILES C(F)(F)(F)S(=O)(=O)[O-].[Ag+];
Properties
Chemical formula	CF3SO3Ag
Molar mass	256.937 g/mol
Odor	odorless
Melting point	286 °C (547 °F; 559 K)
Solubility in water	soluble
Hazards
	GHS labelling:[1]
Pictograms
Signal word	Danger
Hazard statements	H315, H319, H335
Precautionary statements	P260, P261, P264, P271, P280, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P332+P313, P337+P313, P362, P363, P403+P233, P405, P501
NFPA 704 (fire diamond)	1 0 0
Safety data sheet (SDS)	Oxford MSDS
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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).[2][3]

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

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.[4]

Reactions

It is used to prepare alkyl triflates from alkyl halides:[5]

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:[6]

CF₃SO₂OAg + BrRe(CO)₅ → CF₃SO₂ORe(CO)₅ + AgBr

References

"Silver trifluoromethanesulfonate". pubchem.ncbi.nlm.nih.gov. Retrieved 15 December 2021.
R.N. Haszeldine, J.M. Kidd (1954), "Perfluoroalkyl derivatives of sulphur. Part I. Trifluoromethanesulphonic acid", J. Chem. Soc. (in German), pp. 4228–4232, doi:10.1039/JR9540004228
T. Gramstadt, R.N. Haszeldine (1956), "33. Perfluoroalkyl derivatives of sulphur. Part IV. Perfluoroalkanesulphonic acids", J. Chem. Soc. (in German), pp. 173–180, doi:10.1039/JR9560000173
G.M. Whitesides, F.D. Gutowski (1976), "Reaction of α, ω-di-Grignard reagents with silver(I) salts form carbocyclic rings", J. Org. Chem., vol. 41, no. 17, pp. 2882–2885, doi:10.1021/jo00879a019
Stang, Peter J.; Hanack, Michael; Subramanian, L. R. (1982). "Perfluoroalkanesulfonic Esters: Methods of Preparation and Applications in Organic Chemistry". Synthesis. 1982 (2): 85–126. doi:10.1055/s-1982-29711. ISSN 0039-7881. S2CID 94894040.
Steven P. Schmidt; Jay Nitschke; William C. Trogler (1989). "Manganese(I) and Rhenium(I) Pentacarbonyl(Trifluoromethanesulfonato) Complexes". Inorganic Syntheses. Vol. 26. pp. 113–117. doi:10.1002/9780470132579.ch20. ISBN 978-0-470-13257-9.

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[1] "Silver trifluoromethanesulfonate". pubchem.ncbi.nlm.nih.gov. Retrieved 15 December 2021.

[Haszeldine-2] R.N. Haszeldine, J.M. Kidd (1954), "Perfluoroalkyl derivatives of sulphur. Part I. Trifluoromethanesulphonic acid", J. Chem. Soc. (in German), pp. 4228–4232, doi:10.1039/JR9540004228

[Gramstad-3] T. Gramstadt, R.N. Haszeldine (1956), "33. Perfluoroalkyl derivatives of sulphur. Part IV. Perfluoroalkanesulphonic acids", J. Chem. Soc. (in German), pp. 173–180, doi:10.1039/JR9560000173

[Whitesides-4] G.M. Whitesides, F.D. Gutowski (1976), "Reaction of α, ω-di-Grignard reagents with silver(I) salts form carbocyclic rings", J. Org. Chem., vol. 41, no. 17, pp. 2882–2885, doi:10.1021/jo00879a019

[Stang-5] Stang, Peter J.; Hanack, Michael; Subramanian, L. R. (1982). "Perfluoroalkanesulfonic Esters: Methods of Preparation and Applications in Organic Chemistry". Synthesis. 1982 (2): 85–126. doi:10.1055/s-1982-29711. ISSN 0039-7881. S2CID 94894040.

[6] Steven P. Schmidt; Jay Nitschke; William C. Trogler (1989). "Manganese(I) and Rhenium(I) Pentacarbonyl(Trifluoromethanesulfonato) Complexes". Inorganic Syntheses. Vol. 26. pp. 113–117. doi:10.1002/9780470132579.ch20. ISBN 978-0-470-13257-9.