Allyl triflate Chemical Properties

Boiling point:

16.6°C

Density 

1.456 (estimate)

solubility 

sol chlorinated hydrocarbons.

color 

colorless liquid.

Allyl triflate Usage And Synthesis

Synthesis Reference(s)

The Journal of Organic Chemistry, 42, p. 3109, 1977 DOI: 10.1021/jo00439a001

Synthesis

Allyl triflate is prepared by the reaction of Trifluoromethanesulfonic Anhydride (1 equiv) and allyl alcohol (1 equiv) in the presence of pyridine (1 equiv) in carbon tetrachloride at 0 °C.¹ The insoluble pyridine salt is removed by filtration through sodium sulfate, and the resulting solution is used directly for allylation reactions. The yield of the reaction is reported to be 75 ± 5% based on quantitative NMR analysis of aliquots.

storage

Allyl triflate must be stored at -78 °C in a vented flask. The half-life of the neat reagent is ~10 min at room temperature, and the reagent in carbon tetrachloride solution completely decomposed in 3 days at room temperature. Allyl triflate reacts violently with nitrogen, or oxygen-containing solvents such as DMSO, DMF, or acetonitrile. The reagent is an extremely reactive allylating agent, and contact or inhalation should be avoided. Use in a fume hood.

References

1. Beard, C. D.; Baum, K.; Grakauskas, V. JOC 1973, 38, 3673.