| Identification | More | [Name]
PENTAFLUOROPHENYL TRIFLUOROACETATE | [CAS]
14533-84-7 | [Synonyms]
TFA-OPFP
PFP-O-TFA
PENTAFLUORPHENYL TRIFLUORACETATE
pentafluorophenyl trifloroacetate
PENTAFLUOROPHENYL TRIFLUOROACETATE
Pentafluoropfenyl Trifluoroacetate
PentafluorophenylTrifluoroacetate>
Pentafluorophenyl trifluoroacetate 98%
perfluorophenyl 2,2,2-trifluoroacetate
Pentafluorophenyl trifluoroacetate, 98+%
TRIFLUORO ACETIC ACID PENTAFLUORO PHENYL ESTER
2,2,2-Trifluoro-acetic Acid 2,3,4,5,6-Pentafluorophenyl Ester
Acetic acid,2,2,2-trifluoro-, 2,3,4,5,6-pentafluorophenyl ester
Perfluoro(phenyl acetate), Trifluoroacetic acid pentafluorophenyl ester
Pentafluorophenyl trifluoroacetate,Trifluoroacetic acid pentafluorophenyl ester | [EINECS(EC#)]
629-320-4 | [Molecular Formula]
C8F8O2 | [MDL Number]
MFCD00134438 | [Molecular Weight]
280.07 | [MOL File]
14533-84-7.mol |
| Chemical Properties | Back Directory | [Appearance]
Clear colorless liquid | [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.)
| [Fp ]
126 °F
| [storage temp. ]
Store at RT. | [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 Data | Back Directory | [Hazard Codes ]
Xi,F | [Risk Statements ]
R10:Flammable.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S16:Keep away from sources of ignition-No smoking .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [RIDADR ]
UN 3272 3/PG 3
| [WGK Germany ]
3
| [HazardClass ]
3.2 | [PackingGroup ]
III | [HS Code ]
29159000 |
| Hazard Information | Back Directory | [Chemical Properties]
Clear colorless liquid | [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.
| [Uses]
It is used as a pharmaceutical intermediate. | [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 |
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