Silver trifluoromethanesulfonate

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Silver trifluoromethanesulfonate
Names
IUPAC name
silver trifluoromethanesulfonate
Other names
Silver triflate
Identifiers
3D model (
JSmol
)
Abbreviations AgOTf
ChemSpider
ECHA InfoCard
 100.018.985 Edit this at Wikidata
EC Number
  • 220-882-2
UNII
  • 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
  • C(F)(F)(F)S(=O)(=O)[O-].[Ag+]
Properties
CF3SO3Ag
Molar mass 256.937 g/mol
Odor odorless
Melting point 286 °C (547 °F; 559 K)
soluble
Hazards
GHS labelling:[1]
GHS05: CorrosiveGHS07: Exclamation mark
Danger
H315, H319, H335
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)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
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).
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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

dilute sulfuric acid, which is then neutralized with silver carbonate (Ag2CO3).[2][3]

The silver triflate is thereby obtained in a yield of 95% and can be

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

bromopentacarbonylrhenium can be converted to the more labile derivative using silver triflate:[6]

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

References

  1. ^ "Silver trifluoromethanesulfonate". pubchem.ncbi.nlm.nih.gov. Retrieved 15 December 2021.
  2. doi:10.1039/JR9540004228
  3. doi:10.1039/JR9560000173
  4. doi:10.1021/jo00879a019
  5. S2CID 94894040
    .
  6. ISBN 978-0-470-13257-9
    .
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