Bis(pentafluorophenyl) carbonate
[CAS# 59483-84-0]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ester >> Acid ester compound
• Name: Bis(pentafluorophenyl) carbonate
• Synonyms: Dipentafluorophenylcarbonate
• Molecular Formula: C₁₃F₁₀O₃
• Molecular Weight: 394.12
• CAS Registry Number: 59483-84-0
• EC Number: 671-619-7
• SMILES: C1(=C(C(=C(C(=C1F)F)F)F)F)OC(=O)OC2=C(C(=C(C(=C2F)F)F)F)F

Properties

• Density: 1.8±0.1 g/cm³, Calc.^*
• Melting point: 47-50 °C (Expl.)
• Index of Refraction: 1.448, Calc.^*
• Boiling Point: 286.5±40.0 °C (760 mmHg), Calc.^*
• Flash Point: 123.1±22.2 °C, Calc.^*, 110 °C (Expl.)

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

Bis(pentafluorophenyl) carbonate is an organic compound composed of a carbonate group (CO3) bonded to two pentafluorophenyl groups (C6HF5). It is a fluorinated aromatic compound that has gained attention in chemical and industrial applications due to its unique structural properties and reactivity.

The discovery of bis(pentafluorophenyl) carbonate is closely related to the broader study of fluorinated organic compounds, which are known for their stability, high chemical resistance, and specialized reactivity. The introduction of pentafluorophenyl groups in place of hydrogen atoms on a phenyl ring significantly alters the physical and chemical characteristics of the compound. This makes bis(pentafluorophenyl) carbonate valuable in specific applications where such properties are required.

The compound is primarily used as a reagent in organic synthesis. It is an effective electrophilic source of the pentafluorophenyl group, which can be transferred to various substrates. This reactivity is harnessed in the synthesis of a variety of compounds, including those used in pharmaceuticals, agrochemicals, and materials science. In particular, bis(pentafluorophenyl) carbonate is utilized in the synthesis of polycarbonate polymers. The pentafluorophenyl group, due to its electron-withdrawing nature, can enhance the mechanical and thermal properties of the resulting polymers. These polycarbonates exhibit improved resistance to high temperatures and chemical attack, making them useful in demanding applications such as electronics and aerospace.

Another important application of bis(pentafluorophenyl) carbonate is in the field of high-performance coatings. The presence of the pentafluorophenyl groups imparts excellent chemical stability and resistance to degradation under harsh conditions. As a result, coatings based on bis(pentafluorophenyl) carbonate can be applied to materials that need to withstand exposure to corrosive environments, such as in the automotive, electronics, and chemical processing industries.

In addition to its use in polymer chemistry and coatings, bis(pentafluorophenyl) carbonate also plays a role in the synthesis of specialized fluorinated compounds. The pentafluorophenyl group is highly valued in medicinal chemistry for its ability to modulate the pharmacological properties of drug candidates. It can enhance the metabolic stability and bioavailability of certain pharmaceuticals, making bis(pentafluorophenyl) carbonate a valuable tool in the development of new therapeutic agents.

Bis(pentafluorophenyl) carbonate is also utilized in the preparation of various fluorinated materials, which are important in the development of advanced electronic devices. The unique properties of the pentafluorophenyl group, such as its high electronegativity and its ability to form stable compounds, make it suitable for the creation of functional materials used in organic electronics, such as organic light-emitting diodes (OLEDs) and organic semiconductors.

In summary, bis(pentafluorophenyl) carbonate is a fluorinated compound with significant applications in organic synthesis, polymer chemistry, coatings, and materials science. Its chemical structure, which includes the electron-withdrawing pentafluorophenyl groups, imparts unique properties such as increased stability and resistance to harsh conditions. This makes it valuable in a range of industrial applications, from the creation of high-performance polymers and coatings to the development of specialized fluorinated compounds for the pharmaceutical and electronics industries.

References

1989. Dipentafluorophenyl carbonate--a reagent for peptide synthesis. Bioorganicheskaia khimiia, 15(4).
URL: https://pubmed.ncbi.nlm.nih.gov/2751706

1993. Dipentafluorophenyl carbonate--a reagent for the synthesis of oligonucleotides and their conjugates. Nucleic Acids Research, 21(23).
DOI: 10.1093/nar/21.23.5337

2021. Catalytic and non-catalytic amidation of carboxylic acid substrates. Molecular Diversity, 26(3).
DOI: 10.1007/s11030-021-10252-0