Methyl trifluoromethansulfonate

From Wikipedia, the free encyclopedia
Methyl triflate
IUPAC name

Methyl trifluoromethanesulfonate

Other names

Trifluoromethanesulfonic acid, methyl ester
Triflic acid, methyl ester, methyl triflate

Identifiers
CAS number 333-27-7 YesY
PubChem 9526
ChemSpider 9153 YesY
Jmol-3D images Image 1
Properties
Molecular formula C2H3F3O3S
Molar mass 164.10 g/mol
Appearance Colourless Liquid
Density 1.496 g/mL
Melting point −64 °C; −83 °F; 209 K
Boiling point 100 °C; 212 °F; 373 K
Solubility in water Hydrolyzes
Hazards
R-phrases R10, R34
S-phrases S26, S36/37/39, S45
Main hazards Corrosive
Flash point 38 °C; 100 °F; 311 K
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Methyl trifluoromethanesulfonate, commonly abbreviated MeOTf, is the organic compound with the formula CF3SO2OCH3. It is a colourless liquid that is a very powerful (and very dangerous) methylating reagent in chemistry.[1]

Reactivity

This compound is closely related to methyl fluorosulfonate (FSO2OCH3), which is an older and less common reagent. These compounds alkylate faster and with wider range of substrates than traditional methylating agents such as methyl iodide. One ranking of alkylating agents is (CH3)3O+ > CF3SO2OCH3 ~ FSO2OCH3 > (CH3)2SO4> CH3I. It will alkylate many functional groups that are only weakly basic such as aldehydes, amides, and nitriles. It does not methylate benzene or the bulky 2,6-di-tert-butylpyridine.[1] Its ability to methylate N-heterocycles is exploited in certain deprotection schemes.[2]

See also

  • Triflate
  • Magic methyl

References

  1. ↑ 1.0 1.1 Roger W. Alder, Justin G. E. Phillips, Lijun Huang, Xuefei Huang, "Methyltrifluoromethanesulfonate" Encyclopedia of Reagents for Organic Synthesis 2005 John Wiley & Sons, doi:10.1002/047084289X.rm266m.pub2
  2. ↑ Albert I. Meyers and Mark E. Flanagan. (1998), "2,2'-Dimethoxy-6-formylbiphenyl", Org. Synth. ; Coll. Vol. 9: 258 
This article is issued from Wikipedia. The text is available under the Creative Commons Attribution/Share Alike; additional terms may apply for the media files.