Pentafluorophenyl trifluoroacetate

Chemical Properties

Uses

• In the esterification of 2′-carboxyrhodamine dye to form pentafluorophenyl ester as a single isomer.
• As an acylating agent and a coupling agent for the peptide-type coupling of N-substituted glycine oligomers.
• In the synthesis of pentafluorophenyl thiophene-3-acetate (PFPTA) by reacting with 3-thiopheneacetic acid.

Uses

Synthesis

771-61-9

407-25-0

14533-84-7

1. Pentafluorophenol (50.0 g, 271 mmol) was mixed with trifluoroacetic anhydride (85.0 g, 404 mmol) and the reaction was stirred at 40 °C for 18 hours. 2. The reaction mixture was fractionally distilled and the fractions with boiling points of 122-125 °C were collected to afford trifluoroacetate of pentafluorophenol (75.2 g, 99% yield) as a colorless liquid. 3. in another reaction vessel, oleic acid (30.0 g, 106 mmol) was dissolved in anhydrous DMF (100 mL), and then anhydrous DMF (100 mL) solution of pentafluorophenol trifluoroacetate (32.7 g, 116 mmol) was added. 4. Pyridine (9.16 g, 116 mmol) was slowly added to the above mixture and the reaction was stirred at room temperature for 18 hours. 5. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (200 mL) and washed sequentially with 0.1N hydrochloric acid (100 mL), saturated sodium bicarbonate solution (100 mL) and brine (50 mL). 6. The organic layer was separated, dried with anhydrous magnesium sulfate and concentrated in vacuum to afford oleate pentafluoroacetate (45.0 g, 95% yield) as a colorless viscous liquid.

References