Methyl 2,2-difluoro-2-(fluorosulfonyl)acetate
[CAS# 680-15-9]

Identification

• Classification: Organic raw materials >> Organic sulfur compound
• Name: Methyl 2,2-difluoro-2-(fluorosulfonyl)acetate
• Molecular Formula: C₃H₃F₃O₄S
• Molecular Weight: 192.11
• CAS Registry Number: 680-15-9
• EC Number: 629-185-1
• SMILES: COC(=O)C(F)(F)S(=O)(=O)F

Properties

• Density: 1.509
• Boiling point: 117-118 °C
• Refractive index: 1.351
• Flash point: 47 °C

Safety Data

• Hazard Symbols: GHS02;GHS05 Danger
• Risk Statements: H226-H314
• Safety Statements: P210-P233-P240-P241-P242-P243-P260-P264-P280-P301+P330+P331-P302+P361+P354-P303+P361+P353-P304+P340-P305+P354+P338-P316-P321-P363-P370+P378-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable liquids	Flam. Liq.	3	H226
Skin corrosion	Skin Corr.	1B	H314
Serious eye damage	Eye Dam.	1	H318
Skin corrosion	Skin Corr.	1C	H314

• Transport Information: UN 2920

Discovery and Applications

Methyl 2,2-difluoro-2-(fluorosulfonyl)acetate is an organofluorine compound that has gained attention for its reactivity and application in organic synthesis. It features a methyl ester group attached to a difluorinated carbon, which is further bonded to a fluorosulfonyl group. This structural combination of fluorine and sulfonyl groups imparts the compound with unique chemical properties, making it a valuable reagent in various chemical transformations.

The discovery of methyl 2,2-difluoro-2-(fluorosulfonyl)acetate emerged from research focused on the synthesis of fluorinated organic compounds. Fluorinated chemicals are widely used in the development of pharmaceuticals, agrochemicals, and advanced materials because of their stability, bioactivity, and ability to modify the behavior of organic molecules. The presence of both fluorine atoms and the reactive fluorosulfonyl group in this compound allows it to participate in diverse reactions, including nucleophilic substitution, addition reactions, and more specialized synthetic processes.

One of the primary applications of methyl 2,2-difluoro-2-(fluorosulfonyl)acetate is in the preparation of fluorinated building blocks for drug development. Fluorinated esters such as this are particularly useful for modifying the pharmacological properties of molecules, improving their metabolic stability, bioavailability, and potency. The compound is often used to introduce fluorine atoms into molecules at key positions, which can significantly alter their interaction with biological targets.

In addition to pharmaceutical applications, methyl 2,2-difluoro-2-(fluorosulfonyl)acetate plays a role in the synthesis of specialty chemicals, particularly those used in the manufacture of materials with enhanced durability and performance. Fluorinated materials are valued in industries such as electronics, aerospace, and energy storage due to their exceptional resistance to heat, chemicals, and mechanical stress. This compound serves as a starting material for producing these high-performance materials, where the combination of fluorine and sulfonyl functionality is crucial for achieving the desired properties.

Ongoing research into fluorinated reagents like methyl 2,2-difluoro-2-(fluorosulfonyl)acetate continues to uncover new applications, particularly in the context of green chemistry. Its reactivity offers opportunities for more sustainable and efficient synthetic methods, contributing to the development of environmentally friendly technologies.

References

2012. Methyl 2,2-Difluoro-2-(fluorosulfonyl)acetate, a Difluorocarbene Reagent with Reactivity Comparable to That of Trimethylsilyl 2,2-Difluoro-2-(fluorosulfonyl)acetate (TFDA). The Journal of Organic Chemistry, 77(10).
DOI: 10.1021/jo300876z

2021. Contemporary synthetic strategies in organofluorine chemistry. Nature Reviews Methods Primers, 1(1).
DOI: 10.1038/s43586-021-00042-1

2024. SuFEx Click Chemistry: Discovery to Applications. Materials Horizons: From Nature to Nanomaterials, 1(1).
DOI: 10.1007/978-981-97-4596-8_8