2-(Fluorosulfonyl)difluoroacetic acid
[CAS# 1717-59-5]

Identification

• Classification: Chemical reagent >> Fluorine reagent
• Name: 2-(Fluorosulfonyl)difluoroacetic acid
• Synonyms: 2,2-Difluoro-2-(fluorosulfonyl)acetic acid
• Molecular Formula: C₂HF₃O₄S
• Molecular Weight: 178.09
• CAS Registry Number: 1717-59-5
• EC Number: 629-236-8
• SMILES: C(=O)(C(F)(F)S(=O)(=O)F)O

Properties

• Density: 1.723
• Boiling point: 153 °C
• Refractive index: 1.36
• Flash point: >110 °C

Safety Data

• Hazard Symbols: GHS05;GHS06 Danger
• Risk Statements: H300-H310-H314-H330
• Safety Statements: P260-P262-P264-P270-P280-P301+P316-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P354+P338-P316-P321-P330-P361+P364-P363-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	2	H300
Acute toxicity	Acute Tox.	1	H310
Skin corrosion	Skin Corr.	1A	H314
Skin corrosion	Skin Corr.	1B	H314
Acute toxicity	Acute Tox.	2	H310
Serious eye damage	Eye Dam.	1	H318
Flammable liquids	Flam. Liq.	3	H226
Acute toxicity	Acute Tox.	1	H300

• Transport Information: UN 1760

Discovery and Applications

2-(Fluorosulfonyl)difluoroacetic acid is a fluorinated compound with significant interest in organic chemistry due to its highly reactive sulfonyl and fluorinated groups. The structure of the molecule consists of a central carbon atom bonded to a fluorosulfonyl group (SO₂F), two fluorine atoms, and a carboxyl group. Its discovery and utility stem from the growing demand for fluorinated organic compounds in a range of industrial and scientific applications.

The discovery of 2-(Fluorosulfonyl)difluoroacetic acid is linked to advancements in fluorine chemistry and the development of new reagents for organic synthesis. Fluorine atoms impart unique properties to organic molecules, such as increased stability, bioavailability, and altered electronic properties. The fluorosulfonyl group further enhances the compound’s reactivity, making it useful as an intermediate in various chemical transformations, especially in the synthesis of pharmaceuticals and agrochemicals.

In synthetic chemistry, 2-(Fluorosulfonyl)difluoroacetic acid serves as a precursor for introducing both fluorine and sulfonyl groups into complex molecules. These functional groups are highly valued in medicinal chemistry for their ability to modify the pharmacokinetics and biological activity of drug candidates. Fluorinated compounds often show improved metabolic stability and increased potency, which has driven the use of this reagent in the design of novel therapeutics.

Additionally, 2-(Fluorosulfonyl)difluoroacetic acid is employed in the production of specialty chemicals, including those used in electronics and materials science. The incorporation of fluorine into polymers and other materials can enhance their chemical resistance, thermal stability, and mechanical properties. As a result, this compound is valuable in the preparation of advanced materials used in demanding environments, such as coatings, batteries, and electronic devices.

Research continues to explore new applications of 2-(Fluorosulfonyl)difluoroacetic acid, particularly in the context of developing sustainable and efficient chemical processes. Its potential for contributing to the synthesis of environmentally benign products is of growing interest in green chemistry initiatives.

References

2018. Transition-Metal-Free Efficient Synthesis of Bisindole Sulfanes Using 2-(Fluorosulfonyl)difluoroacetic Acid. Synlett, 29(12).
DOI: 10.1055/s-0037-1609573

2023. Photochemical degradation pathways and near-complete defluorination of chlorinated polyfluoroalkyl substances. Nature Water, 1(4).
DOI: 10.1038/s44221-023-00046-z

2014. Recent Advances in the Synthetic Application of Difluorocarbene. Synthesis, 46(04).
DOI: 10.1055/s-0033-1340856.