1,1,2,2,3,3,4,4-Octafluoro-1,4-butanedisulfonyl difluoride
[CAS# 84246-31-1]

Identification

• Classification: Chemical reagent >> Organic reagent >> Sulfonyl halide
• Name: 1,1,2,2,3,3,4,4-Octafluoro-1,4-butanedisulfonyl difluoride
• Molecular Formula: C₄F₁₀O₄S₂
• Molecular Weight: 366.15
• CAS Registry Number: 84246-31-1
• SMILES: C(C(C(F)(F)S(=O)(=O)F)(F)F)(C(F)(F)S(=O)(=O)F)(F)F

Discovory and Applicatios

1,1,2,2,3,3,4,4-Octafluoro-1,4-butanedisulfonyl difluoride is a perfluorinated organosulfonyl compound characterized by a four-carbon linear backbone in which all hydrogen atoms are replaced by fluorine atoms, and both terminal carbon atoms are substituted with sulfonyl fluoride groups (–SO₂F). Its molecular formula is C₄F₁₀O₄S₂, and the structure reflects a highly fluorinated and electrophilic molecule with significant utility in materials and fluorine chemistry.

The compound belongs to a class of reagents known as perfluoroalkylene disulfonyl fluorides. These compounds are of interest for their dual functionality: the perfluorinated alkyl chain imparts chemical inertness and thermal stability, while the sulfonyl fluoride groups are reactive electrophiles that can participate in substitution and addition reactions, particularly with nucleophiles such as amines, alcohols, and thiols. The sulfonyl fluoride functionality is also resistant to hydrolysis under neutral conditions, giving the compound a stable profile during synthesis and storage.

1,1,2,2,3,3,4,4-Octafluoro-1,4-butanedisulfonyl difluoride has been used as a bifunctional crosslinking agent and monomer precursor in the synthesis of specialty fluoropolymers and sulfonated membranes. Its high thermal and oxidative stability make it suitable for incorporation into materials designed for harsh chemical environments. It has been particularly explored in the development of proton exchange membranes (PEMs) for fuel cells, where sulfonated polymers serve as proton conductors. The introduction of such perfluorinated disulfonyl moieties into polymer backbones or side chains can enhance both the chemical durability and the proton conductivity of the material.

The synthesis of this compound typically involves the reaction of tetrafluoroethylene or other perfluorobutane precursors with sulfur trioxide or chlorosulfonic acid, followed by fluorination using agents such as hydrogen fluoride or sulfur tetrafluoride. Alternatively, fluorosulfonyl intermediates can be prepared and then subjected to selective perfluorination steps to yield the target structure. Careful control of reaction temperature, solvent system, and moisture exclusion is necessary due to the high reactivity of the intermediates and products.

In analytical chemistry, this compound is characterized using techniques such as nuclear magnetic resonance (especially ¹⁹F NMR for fluorine atoms), infrared spectroscopy (with diagnostic S=O and S–F stretching bands), and mass spectrometry. The symmetrical structure simplifies the spectral interpretation, while also contributing to its potential use in materials requiring uniform molecular architecture.

Due to the presence of sulfonyl fluoride groups, 1,1,2,2,3,3,4,4-octafluoro-1,4-butanedisulfonyl difluoride is reactive toward nucleophiles and has been utilized in bioconjugation chemistry as part of emerging sulfonyl fluoride-based covalent inhibitors. Although it is less commonly employed in biological systems than aryl sulfonyl fluorides, it demonstrates the general utility of this functional group in forming stable sulfonamide and related linkages.

From a safety perspective, compounds with reactive sulfonyl fluoride groups should be handled with care, as they may cause irritation to the skin, eyes, or respiratory system upon contact or inhalation. Their reactivity also necessitates appropriate handling under anhydrous and inert conditions when used in synthesis. As a perfluorinated compound, environmental persistence and bioaccumulation are potential concerns, and proper disposal according to regulatory guidelines is recommended.

In summary, 1,1,2,2,3,3,4,4-octafluoro-1,4-butanedisulfonyl difluoride is a chemically stable yet functionally reactive compound used in advanced material synthesis and fluorinated polymer design. Its dual sulfonyl fluoride groups enable bifunctional reactivity, while the perfluorinated backbone contributes to high chemical resistance and thermal stability, making it suitable for specialized industrial and research applications.

References

2017. Bifluoride-catalysed sulfur(VI) fluoride exchange reaction for the synthesis of polysulfates and polysulfonates. Nature Chemistry.
DOI: 10.1038/nchem.2796