4-Fluoro-1,3-dioxolan-2-one
[CAS# 114435-02-8]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: 4-Fluoro-1,3-dioxolan-2-one
• Synonyms: Fluoroethylene carbonate
• Molecular Formula: C₃H₃FO₃
• Molecular Weight: 106.05
• CAS Registry Number: 114435-02-8
• EC Number: 483-360-5
• SMILES: C1C(OC(=O)O1)F

Properties

• Density: 1.454

Safety Data

• Hazard Symbols: GHS07;GHS08 Danger
• Risk Statements: H302-H315-H317-H319-H372
• Safety Statements: P260-P261-P264-P264+P265-P270-P272-P280-P301+P317-P302+P352-P305+P351+P338-P319-P321-P330-P332+P317-P333+P317-P337+P317-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin sensitization	Skin Sens.	1	H317
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - repeated exposure	STOT RE	1	H372

Discovery and Applications

4-Fluoro-1,3-dioxolane-2-one is an organic compound with the chemical formula C₃H₃FO₃ and a molecular weight of 106.05 g/mol. It is characterized by the substitution of the dioxolane ring with a fluorine atom, making it a fluorinated cyclic carbonate. The compound has a unique chemical structure and reactivity, and has valuable applications in various fields.

The discovery of 4-fluoro-1,3-dioxolane-2-one is related to the advancement of fluorine chemistry and the development of cyclic carbonates. Fluorinated cyclic carbonates have attracted much attention due to their potential in pharmaceuticals, material science, and battery technology. The compound is synthesized by fluorination of 1,3-dioxolane-2-one, a process that enhances the chemical properties of the parent molecule by selectively introducing fluorine.

The synthesis of 4-fluoro-1,3-dioxolane-2-one involves the fluorination of 1,3-dioxolane-2-one using a fluorinating agent under controlled conditions. The method forms fluorinated cyclic carbonates characterized by the introduction of fluorine atoms into the dioxolane ring, which enhances its reactivity and stability.

In the pharmaceutical industry, 4-fluoro-1,3-dioxolane-2-one is a building block for the synthesis of fluorinated drugs and intermediates. Its ability to introduce fluorine atoms into drug molecules enhances their metabolic stability, bioavailability, and overall efficacy. Fluorinated cyclic carbonates are used to develop new drugs with improved properties.

The compound can be applied to lithium-ion batteries as an electrolyte additive or solvent. Its cyclic carbonate structure helps form a stable solid electrolyte interface (SEI) on the battery electrodes, thereby improving the performance, safety, and life of the battery.

In materials science, 4-fluoro-1,3-dioxolane-2-one is used to develop advanced materials, including polymers and coatings. Its fluorinated properties enhance the chemical and thermal stability of the material for high-performance applications such as electronics and specialty coatings.

As a reagent in chemical research, the compound helps study the effects of fluorine on cyclic structures and develop new synthetic methods. Its unique properties allow researchers to explore different reaction pathways and create innovative compounds for a variety of applications.

References

2024. In situ p-block protective layer plating in carbonate-based electrolytes enables stable cell cycling in anode-free lithium batteries. Nature Materials.
DOI: 10.1038/s41563-024-01997-8

2024. Strategies for flame-retardant polymer electrolytes for safe lithium-based batteries. Nano Research.
DOI: 10.1007/s12274-024-6902-4

2012. Enhanced electrochemical performance of LiFePO4 cathode with the addition of fluoroethylene carbonate in electrolyte. Journal of Solid State Electrochemistry.
DOI: 10.1007/s10008-012-1927-9