Perfluorobutanesulfonic anhydride
[CAS# 36913-91-4]

Identification

• Classification: Organic raw materials >> Organic fluorine compound
• Name: Perfluorobutanesulfonic anhydride
• Synonyms: Nonafluorobutanesulfonic acid anhydride; Nonafluorobutanesulfonic anhydride
• Molecular Formula: C₈F₁₈O₅S₂
• Molecular Weight: 582.19
• CAS Registry Number: 36913-91-4
• EC Number: 253-270-9
• SMILES: C(C(C(F)(F)S(=O)(=O)OS(=O)(=O)C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(C(F)(F)F)(F)F

Properties

• Density: 1.9±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.318, Calc.^*
• Boiling Point: 219.3±40.0 ºC (760 mmHg), Calc.^*
• Flash Point: 86.4±27.3 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS05 Danger
• Hazard Statements: H314
• Precautionary Statements: P260-P264-P280-P301+P330+P331-P302+P361+P354-P304+P340-P305+P354+P338-P316-P321-P363-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1B	H314

• Transport Information: UN 3264 8 / PGII

Discovory and Applicatios

Perfluorobutanesulfonic anhydride, also known as perfluorobutanesulfonyl fluoride (PFBS anhydride), is a highly reactive chemical compound with the molecular formula C4HF7O2S. It is an important intermediate in the field of organic chemistry, primarily used in the synthesis of perfluorinated compounds and as a reagent in a variety of chemical reactions.

The discovery of perfluorobutanesulfonic anhydride can be traced back to the continued efforts in the chemical industry to develop more stable and reactive fluorinated compounds. Fluorine, due to its electronegativity, imparts unique properties to molecules, making them highly resistant to chemical reactions and providing them with increased thermal stability. The sulfonic acid derivatives, such as perfluorobutanesulfonic acid, were already known for their utility in industrial applications. The creation of the anhydride form allowed for more efficient reactions and applications, especially in the synthesis of fluorinated compounds.

One of the main applications of perfluorobutanesulfonic anhydride is in the production of perfluorinated surfactants, which are widely used in industries such as electronics, coatings, and manufacturing. Due to the fluorine atoms attached to the molecule, perfluorobutanesulfonic anhydride imparts highly hydrophobic and lipophobic properties to the compounds it is used to synthesize. These properties are useful in applications such as non-stick coatings, waterproofing, and stain-resistant treatments.

Additionally, perfluorobutanesulfonic anhydride is employed in the creation of perfluorinated polymers, which have significant applications in the chemical and semiconductor industries. The stability and non-reactivity of these polymers make them ideal for use in harsh chemical environments, such as in the lining of pipes and tanks that store corrosive substances. Perfluorobutanesulfonic anhydride can also be used as a reagent in the synthesis of fluorinated monomers, which are then polymerized to form high-performance materials.

Perfluorobutanesulfonic anhydride also finds application in the pharmaceutical industry, where it is used to synthesize specialized compounds with unique properties. The ability to introduce fluorine atoms into the molecular structure of organic compounds can significantly alter their chemical and biological behavior, making them useful as drugs or intermediates in drug development. The anhydride is used to modify molecules in ways that improve their stability, solubility, or bioavailability.

In addition to its industrial uses, perfluorobutanesulfonic anhydride has potential applications in the development of new materials and technologies. For example, it is being explored in the design of advanced materials with applications in energy storage, coatings, and high-performance lubricants. The compound’s chemical structure and reactivity make it a useful building block in the development of novel materials for these and other applications.

Despite its versatility, perfluorobutanesulfonic anhydride is highly reactive and requires careful handling. As with many fluorinated compounds, it poses challenges in terms of safety and environmental impact. Researchers are continuously studying the compound to better understand its behavior and to develop safer methods for its use and disposal.

In conclusion, perfluorobutanesulfonic anhydride is a valuable reagent in the field of organic synthesis, with broad applications in industries ranging from pharmaceuticals to material science. Its ability to introduce fluorine atoms into organic molecules makes it a versatile tool in the creation of specialized compounds with unique properties. As research continues, its applications in the development of new materials and technologies are expected to expand, making it a key compound in modern chemistry.

References

2016. Synthesis of Trifluoromethylated Pyridines. Journal of Fluorine Chemistry, 191.
DOI: 10.1016/j.jfluchem.2016.09.008