技术文章

4,5-Difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole: Properties & Uses

4,5-Difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole is a highly fluorinated cyclic monomer bearing four fluorine substituents and two trifluoromethyl groups on a 1,3-dioxole ring, making it a key building block for advanced perfluorinated polymer research.

Chemical Name
4,5-Difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole
SKU
D1530065
Molecular Formula
C5F8O2
Core Scaffold
1,3-Dioxole ring with geminal bis(trifluoromethyl) at C-2 and fluorine at C-4, C-5
Key Feature
High degree of fluorination conferring chemical and thermal stability
Primary Research Use
Perfluorinated polymer and copolymer synthesis (e.g., amorphous fluoropolymers)

Chemical Structure and Physicochemical Properties

4,5-Difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole (molecular formula C₅F₈O₂) is a cyclic compound built on a five-membered 1,3-dioxole ring. The C-2 position carries two trifluoromethyl (–CF₃) groups, while C-4 and C-5 each bear a fluorine atom, yielding a total of eight fluorine atoms per molecule. This arrangement results in an exceptionally electron-poor, chemically inert ring system.

The dense fluorine substitution imparts very low surface energy and high resistance to solvents, acids, and bases. The compound is typically a colorless, volatile liquid or low-boiling liquid under ambient conditions. Its high fluorine content (mass fraction) is characteristic of perfluorinated heterocyclic monomers and is central to its utility in polymer chemistry.

Synthesis and Handling Considerations

Perfluorinated dioxole monomers of this class are generally prepared via fluorination or cyclization strategies starting from hexafluoroacetone and appropriate difluorinated precursors. The synthesis typically requires specialized equipment capable of handling highly fluorinated, reactive intermediates under inert atmospheres.

Due to the high volatility and potential respiratory hazard associated with perfluorinated small molecules, all handling should be performed in a well-ventilated fume hood with appropriate personal protective equipment, including chemically resistant gloves and eye protection. Storage should follow guidelines for volatile, moisture-sensitive fluorinated reagents — typically in sealed containers under inert gas at low temperature.

Researchers should consult the Safety Data Sheet (SDS) for D1530065 prior to use and follow all applicable institutional and regulatory requirements for fluorinated compound handling.

Research Applications in Fluoropolymer Chemistry

The primary research application of 4,5-Difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole is as a monomer for the synthesis of amorphous perfluoropolymers. When copolymerized with tetrafluoroethylene (TFE), this dioxole monomer yields glassy, optically transparent fluoropolymers — commercially known under trade names such as Teflon AF — that combine the chemical inertness of polytetrafluoroethylene (PTFE) with good optical transparency and high gas permeability.

These amorphous fluoropolymers have attracted significant research interest for applications including optical waveguides, gas-permeable membranes, antireflective coatings, and substrates for microelectronics and photolithography. The high free volume generated by the bulky bis(trifluoromethyl) spiro center is responsible for the exceptional gas-transport properties.

Beyond copolymerization, researchers use this monomer to investigate the relationship between fluorine content, ring strain, and polymerizability in perfluorinated cyclic systems. It also serves as a model compound for mechanistic studies in radical and anionic polymerization of fluorinated monomers.

Quality, Purity, and Procurement

For research use, the purity of 4,5-Difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole is critical, as trace impurities can act as chain-transfer agents or inhibitors in free-radical polymerization, significantly affecting polymer molecular weight and dispersity. Aladdin Scientific supplies D1530065 with documented purity specifications; researchers are advised to request a Certificate of Analysis (CoA) and verify purity by ¹⁹F NMR or GC prior to use in sensitive polymerization experiments.

Procurement teams should note that this compound is a specialty fluorinated reagent with limited availability. Early ordering and proper hazardous-materials shipping compliance (fluorinated volatile compounds may be subject to specific transport regulations) are recommended. Contact Aladdin Scientific's technical support for current stock status, bulk pricing, and stability/storage guidance.

Frequently asked questions

What is the molecular formula of 4,5-Difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole?

The molecular formula is C₅F₈O₂. The compound contains eight fluorine atoms: four on the dioxole ring (two ring fluorines at C-4 and C-5, and six from the two trifluoromethyl groups at C-2) distributed across the five-membered heterocyclic scaffold.

What are the main research applications of this compound?

It is primarily used as a monomer in the synthesis of amorphous perfluoropolymers, particularly copolymers with tetrafluoromethylene (TFE) that exhibit optical transparency, chemical inertness, and high gas permeability. Such polymers find use in optical waveguides, gas-separation membranes, antireflective coatings, and microelectronic substrates.

How should D1530065 be stored to maintain stability?

As a volatile, highly fluorinated compound, D1530065 should be stored in tightly sealed containers under an inert atmosphere (e.g., nitrogen or argon) at low temperature, away from moisture and ignition sources. Always consult the product SDS and CoA for specific storage conditions confirmed by Aladdin Scientific.

Why is purity especially important for polymerization applications?

Even trace impurities in fluorinated monomers can act as chain-transfer agents or radical inhibitors during free-radical polymerization, leading to lower molecular weights, broader dispersity, and inconsistent polymer properties. Verifying purity by ¹⁹F NMR or GC before use is strongly recommended.

References

  1. Aladdin Scientific product listing: 4,5-Difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole, SKU D1530065.
  2. Feast, W. J.; Mukhopadhyay, S. Fluoropolymers: Synthesis and Applications. In: Hougham, G. et al. (eds) Fluoropolymers. Springer, 1999. [General reference on perfluorinated dioxole monomers and amorphous fluoropolymers — specific chapter and page numbers require verification]
  3. DuPont technical literature on Teflon AF amorphous fluoropolymers (copolymers of 2,2-bis(trifluoromethyl)-4,5-difluoro-1,3-dioxole and TFE). [Trade name reference; specific document title and publication date require verification]

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.

目录: 技术文章

Da — 若无特别说明,分子量单位默认为道尔顿。   Mw — 重均分子量。   Mn — 数均分子量。

产品仅供科研与开发使用,不用于人体、动物、诊断或治疗。

引用本文

阿拉丁科学.《4,5-Difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole: Properties & Uses》. 阿拉丁知识库,更新于 2026年9月23日。 https://www.aladdin-e.com/zh_cn/faqs/45-difluoro-22-bistrifluoromethyl-13-dioxole-properties-uses-en.html
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