Pentafluorophenyl trifluoroacetate

• Catalog: OFC14533847
• CAS: 14533-84-7
• Category: Trifluoromethylation Agents
• Synonyms: Perfluorophenyl 2,2,2-Trifluoroacetate
• Purity: 98%
• MDL Number: MFCD00134438

• IUPAC Name: (2,3,4,5,6-pentafluorophenyl) 2,2,2-trifluoroacetate
• InChI: InChI=1S/C8F8O2/c9-1-2(10)4(12)6(5(13)3(1)11)18-7(17)8(14,15)16
• InChI Key: VCQURUZYYSOUHP-UHFFFAOYSA-N
• Isomeric SMILES: C1(=C(C(=C(C(=C1F)F)F)F)F)OC(=O)C(F)(F)F
• EC Number: 629-320-4
• Reaxys Registry Number: 2003848

• Molecular Formula: C8F8O2
• Molecular Weight: 280.07
• Melting Point: 4 °C
• Boiling Point: 122 °C
• Flash Point: 52 °C
• Specific Gravity: 1.64
• Refractive Index: 1.37
• Appearance: Colorless to light yellow clear liquid
• Storage: Keep in dark place, inert atmosphere, room temperature
• Stability: Moisture sensitive

• XLogP3-AA: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 2
• Exact Mass: 279.97705454 g/mol
• Monoisotopic Mass: 279.97705454 g/mol
• Topological Polar Surface Area: 26.3Ų
• Heavy Atom Count: 18
• Formal Charge: 0
• Complexity: 303

• HS Number: 2918.99.4700

Case Study

High-Yield Synthesis of Pentafluorophenyl Esters Using Pentafluorophenyl Trifluoroacetate

Green M, et al. Tetrahedron Letters, 1990, 31(41), 5851-5852.

Pentafluorophenyl trifluoroacetate has demonstrated exceptional utility in the efficient synthesis of pentafluorophenyl (Pfp) esters of Nα-Fmoc-protected amino acids. In this method, the reagent acts as an effective acylating agent, activating the carboxylic acid group of the amino acid toward esterification.
The reaction is typically carried out in dry dimethylformamide (DMF) in the presence of pyridine, which functions both as a base and as a nucleophilic catalyst. Under these mild conditions, the Fmoc-protected amino acid (Fmoc-NH-CHR-COOH) reacts with pentafluorophenyl trifluoroacetate, forming the corresponding Pfp ester (Fmoc-NH-CHR-CO-O-C₆F₅) in high yield.
The reaction mechanism involves nucleophilic attack of the amino acid carboxylate on the activated ester bond of the trifluoroacetate derivative, leading to displacement of trifluoroacetate and formation of the highly reactive pentafluorophenyl ester. This activated ester is particularly advantageous for subsequent coupling reactions, including solid-phase peptide synthesis, due to its high reactivity and low by-product formation.

Application of Pentafluorophenyl Trifluoroacetate (PFTFA) in Electrolyte Systems for Mitigating HF-Induced Degradation in Lithium Metal Batteries

Dai S, et al. Journal of Energy Chemistry, 2025, 108, 173-180.

In the pursuit of enhancing lithium metal batteries (LMBs) performance, pentafluorophenyl trifluoroacetate (PFTFA) was experimentally evaluated for its dual-functionality in mitigating HF-induced degradation. The experimental setup involved incorporating PFTFA as a chemical additive into a carbonate-based electrolyte containing LiPF6 and lithium difluoro(oxalato)borate (LiDFOB). The cathode material used was LiNi0.8Co0.1Mn0.1O2 (NCM811). Galvanostatic cycling tests were conducted at a 1 C rate up to 4.4 V to assess the cyclic stability of Li||NCM811 full cells. Additionally, high-voltage cycling at 4.8 V and 0.5 C was performed to validate the additive's protective efficacy under severe conditions. Notably, cells with the PFTFA-containing electrolyte retained 80% capacity over 420 cycles at 4.4 V, outperforming the conventional electrolyte's 54.8% retention after 150 cycles. The results underscore PFTFA's effective HF scavenging and stabilization of the CEI layer, offering a promising strategy for enhancing the longevity and performance of high-voltage LMBs.