Description

Perfluoro-15-crown-5-ether (CAS No. 97571-69-2) is a highly fluorinated cyclic polyether with the molecular formula C₁₀F₂₀O₅. This specialty chemical is characterized by its unique perfluorinated crown ether structure, which imparts exceptional chemical inertness, thermal stability, and lipophobicity. The IUPAC name, 2,2,3,3,5,5,6,6,8,8,9,9,11,11,12,12,14,14,15,15-icosafluoro-1,4,7,10,13-pentaoxacyclopentadecane, reflects its fully fluorinated 15-membered ring with five oxygen atoms. As a fluorinated analog of 15-crown-5, this compound exhibits selective binding properties for cations, particularly in non-polar or supercritical CO₂ environments. Its high electron-withdrawing fluorine content makes it valuable for applications requiring extreme oxidative and chemical resistance. Supplied as a clear, colorless liquid or low-melting solid, it is compatible with fluorinated solvents and finds use in advanced material science, supramolecular chemistry, and specialized extraction processes. Store under inert atmosphere at room temperature.

Properties

• CAS Number: 97571-69-2
• Complexity: 580
• IUPAC Name: 2,2,3,3,5,5,6,6,8,8,9,9,11,11,12,12,14,14,15,15-icosafluoro-1,4,7,10,13-pentaoxacyclopentadecane
• InChI: InChI=1S/C10F20O5/c11-1(12)2(13,14)32-5(19,20)6(21,22)34-9(27,28)10(29,30)35-8(25,26)7(23,24)33-4(17,18)3(15,16)31-1
• InChI Key: CAKZCCWLOCDNJK-UHFFFAOYSA-N
• Exact Mass: 579.9426363
• Molecular Formula: C10F20O5
• Molecular Weight: 580.07
• SMILES: C1(C(OC(C(OC(C(OC(C(OC(C(O1)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F
• Topological: 46.2
• Monoisotopic Mass: 579.9426363
• Synonyms: 97571-69-2, Perfluoro-15-crown-5-ether, perfluoro-1,4,7,10,13-pentaoxacyclopentadecane, DTXSID10379779, HemaGen, DTXCID10330805, perfluoro-15-crown-5, Icosafluoro-15-crown 5-Ether, 2,2,3,3,5,5,6,6,8,8,9,9,11,11,12,12,14,14,15,15-icosafluoro-1,4,7,10,13-pentaoxacyclopentadecane, icosafluoro-1,4,7,10,13-pentaoxacyclopentadecane, MFCD01320747, Icosafluoro-15-crown5-Ether, SCHEMBL884352, AKOS015853259, FS-4526, CS-0435535, I1043, NS00019363, T73107, Icosafluoro-1,4,7,10,13-pentaoxacyclopentadecane, Perfluoro-15-crown-5

Application

Perfluoro-15-crown-5-ether serves as a selective phase-transfer catalyst in fluorinated solvent systems, enabling metal ion extraction in supercritical CO₂ applications. Its fluorinated structure makes it ideal for creating oxygen-resistant materials in aerospace and semiconductor industries. Researchers utilize this crown ether as a building block for designing fluorinated supramolecular architectures with tailored host-guest properties. The compound also finds niche applications in 19F NMR spectroscopy as a chemical shift reference in fluorinated matrices.

Safety and Hazards

GHS Hazard Statements

• H315 (75%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (75%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (50%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Skin Irrit. 2 (75%)
• Eye Irrit. 2 (75%)
• STOT SE 3 (50%)

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