CAS · 14098-44-3
Product Overview
Benzo-15-crown-5丨CAS 14098-44-3 is a member of the crown ether family, characterized by a cyclic polyether structure containing several ether oxygens capable of selectively binding metal cations. The benzene ring fused to the crown ether increases the rigidity and lipophilicity of the molecule, altering its binding properties and solubility compared to parent 15-crown-5.
Product Specifications
| Appearance | White to off-white solid |
|---|---|
| Purity (GC) | 99% min |
| Purity (HPLC) | 99% min |
| HNMR | Consistent with the reference substance |
| Melting Point | 78-83°C |
| Water | 0.4% max |
Applications
1. Selective Cation Complexation
● Benzo-15-crown-5 exhibits high selectivity for alkali metal ions, especially sodium (Na⁺) and potassium (K⁺) due to the size of its cavity (~1.7 Å).
● The aromatic ring modifies the electron density and provides additional interactions, enhancing complex stability.
● Used in ion transport, ion-selective electrodes, and phase transfer catalysis.
2. Phase Transfer Catalyst
● Facilitates the transfer of metal cations from aqueous to organic phases by encapsulating the cation.
● Enhances rates of reactions involving alkali metal salts in organic solvents.
● Useful in organic synthesis for alkylation, nucleophilic substitution, and polymerization reactions.
3. Molecular Recognition and Sensors
● Utilized in designing chemical sensors and ion-selective electrodes that detect alkali metals.
● The aromatic ring allows for fluorescent labeling or attachment to surfaces for sensor construction.
4. Supramolecular Chemistry
● Serves as a building block in supramolecular assemblies and host-guest systems.
● Can be used to construct molecular machines, ion channels, or catalytic systems mimicking biological processes.
5. Extraction and Separation
● Used for selective extraction of metal ions from mixtures, including waste treatment and recovery of valuable metals.
● Its selectivity aids in separating sodium or potassium ions from other competing ions.
Benefits
1. High Selectivity and Affinity
● The crown ether cavity size and benzene ring influence provide high selectivity for sodium and potassium.
● Enables efficient and selective ion complexation, critical for analytical and synthetic applications.
2. Enhanced Lipophilicity
● Benzene ring increases lipophilicity, allowing better solubility in organic solvents.
● Useful for reactions or extractions in non-aqueous environments.
3. Thermal and Chemical Stability
● Crown ethers are generally stable under moderate thermal and chemical conditions.
● Suitable for use in a wide range of solvents and reaction conditions.
4. Versatility in Functionalization
● The aromatic ring can be functionalized further for immobilization on solid supports or incorporation into polymers and sensors.
● Provides a platform for designing advanced supramolecular architectures.
Conclusion
Benzo-15-crown-5丨CAS 14098-44-3 is a versatile crown ether known for its selective complexation of alkali metal ions, particularly sodium and potassium. Its benzene-fused structure enhances selectivity and solubility, making it valuable in analytical chemistry, phase transfer catalysis, supramolecular chemistry, and sensor development. The compound's chemical robustness and adaptability continue to make it a key reagent in both fundamental research and industrial applications involving ion recognition and transport.
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