PENTAFLUOROPHENYL TRIFLUOROACETATE Chemical Properties

Melting point:

4°C(lit.)

Boiling point:

122-123 °C (lit.)

Density 

1.63 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.368(lit.)

Flash point:

126 °F

storage temp. 

Keep in dark place,Sealed in dry,2-8°C

form 

Oil

color 

Clear colorless

Specific Gravity

1.630

Water Solubility 

Soluble in water at 122.5°Cat760mmHg.

Sensitive 

Moisture Sensitive

BRN 

2003848

InChI

InChI=1S/C8F8O2/c9-1-2(10)4(12)6(5(13)3(1)11)18-7(17)8(14,15)16

InChIKey

VCQURUZYYSOUHP-UHFFFAOYSA-N

SMILES

C(OC1=C(F)C(F)=C(F)C(F)=C1F)(=O)C(F)(F)F

CAS DataBase Reference

14533-84-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,F

Risk Statements 

10-36/37/38

Safety Statements 

16-26-36

RIDADR 

UN 3272 3/PG 3

WGK Germany 

3

HazardClass 

3.2

PackingGroup 

III

HS Code 

29159000

MSDS

• Language:English Provider:SigmaAldrich

PENTAFLUOROPHENYL TRIFLUOROACETATE Usage And Synthesis

Chemical Properties

Clear colorless liquid

Uses

It is used as a pharmaceutical intermediate.

Uses

Pentafluorophenyl trifluoroacetate can be used:

• 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.

Synthesis

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

[1] Patent: WO2006/136460, 2006, A2. Location in patent: Page/Page column 32
[2] Tetrahedron Letters, 1990, vol. 31, # 41, p. 5851 - 5852

PENTAFLUOROPHENYL TRIFLUOROACETATE(14533-84-7)Related Product Information

• α-Bromo-2,3,4,5,6-pentafluorotoluene
• O-(2,2,2-Trifluoroethyl)hydroxylamine hydrochloride
• TRIFLUOROACETALDEHYDE HYDRATE
• PENTAFLUOROPHENYLHYDRAZINE
• TRIFLUOROMETHANESULFONIC ACID TRIFLUOROMETHYL ESTER
• Tetramethylammonium trifluoromethanethiolate
• Phthalates
• Lithium hydroxide
• Pentafluorophenol
• Methyl trifluoroacetate
• PENTAFLUOROPHENYL TRIFLUOROACETATE
• 2,3,4,5,6-PENTAFLUOROANISOLE
• PHENYL TRIFLUOROACETATE
• 2,3,5,6-Tetrafluorophenol
• Trifluoroacetic acid
• 2,3,5,6-TETRAFLUOROANISOLE
• 2,3,5,6-TETRAFLUOROPHENYL TRIFLUOROACETATE
• PENTAFLUORO-(2,2,2-TRIFLUOROETHOXY)BENZENE