Products
18-Crown-6
Synonyms:18-Crownether-6;18-Crown-6 ether;Ethylene oxide cyclic hexamer;NSC159836;1,4,7,10,13,16-Hexaoxacyclooctadecane;
Chemical Property of 18-Crown-6
● Appearance/Colour:slightly yellow solid
● Vapor Pressure:4.09E-06mmHg at 25°C
● Melting Point:42-45 ºC(lit.)
● Refractive Index:1.404
● Boiling Point:395.8 ºC at 760 mmHg
● Flash Point:163.8 ºC
● PSA：55.38000
● Density:0.995 g/cm3
● LogP:0.09960
● Storage Temp.:Store at 0-5°C
● Sensitive.:Hygroscopic
● Solubility.:Chloroform (Slightly), Methanol (Very Slightly)
● Water Solubility.:SOLUBLE
● XLogP3:-0.7
● Hydrogen Bond Donor Count:0
● Hydrogen Bond Acceptor Count:6
● Rotatable Bond Count:0
● Exact Mass:264.15728848
● Heavy Atom Count:18
● Complexity:108
Safty Information
● Pictogram(s):
Xn,
Xi
● Hazard Codes:Xn,Xi
● Statements:22-36/37/38-36-20/22-20/21/22
● Safety Statements:26-36-39
Useful
Chemical Classes:Other Classes -> Other Organic Compounds
Canonical SMILES:C1COCCOCCOCCOCCOCCO1
Uses:A useful phase transfer catalyst. 18-Crown-6 is used as an efficient phase transfer catalyst and as a complexing agent with a variety of small cation. It is involved in the synthesis of diaryl ethers, diaryl thioethers, and diarylamines mediated by potassium fluoride-alumina and 18-crown-6. It facilitates the solubility of potassium permanganate in benzene, which is used for oxidizing the organic compounds. It is used to accelerate various substitution reactions as well as enhances the power of nucleophiles such as potassium acetate. It is utilized in the alkylation reactions in the presence of potassium carbonate, N-alkylation of glutarimide and succinimide with dimethylcarbonate. The complex formed by its reaction with potassium cyanide acts as a catalyst in the cyanosilylation of aldehydes, ketones and quinines with trimethylsilyl cyanide (TMSCN). 18-Crown-6 may be used to catalyze the N-alkylation of heterocyclic compounds and allylation of functionalized aldehydes.
Detailed Introduction
18-Crown-6 is a cyclic ether compound with the chemical formula C12H24O6. It is named "18-Crown-6" because it contains a ring of six oxygen atoms, forming a crown-like structure, and has 18 carbon atoms in total. It is a colorless, crystalline solid that is soluble in organic solvents but relatively insoluble in water.
The name "crown" is derived from the compound's structural resemblance to a crown due to the six oxygen atoms arranged in a circular pattern. This unique structure gives 18-Crown-6 its special properties and enables it to be widely used in various applications.
One of the key characteristics of 18-Crown-6 is its ability to complex with metal ions. The oxygen atoms in the crown ring can coordinate with metal cations, such as potassium, sodium, or calcium, to form stable coordination complexes. This property makes 18-Crown-6 a widely used compound in the field of coordination chemistry.
Application
The complexation of metal ions by 18-Crown-6 can have several applications:
Phase transfer catalyst: Like benzyltrimethylammonium chloride, 18-Crown-6 can also act as a phase transfer catalyst. It aids in transferring charged species, such as metal ions, between immiscible phases, enabling reactions that would otherwise be difficult or impossible. The crown ether cavity can encapsulate metal cations, allowing them to pass through membranes or transfer between different solvents.
Metal ion extraction and separation: 18-Crown-6 is often used in solvent extraction techniques to selectively extract and separate specific metal ions from complex mixtures. Its ability to bind with certain metal cations allows for the isolation and purification of these ions from a mixture.
Ion recognition and sensing: The complexation of metal ions by 18-Crown-6 can be utilized in the design of chemical sensors and ion-selective electrodes. By incorporating 18-Crown-6 into sensor systems, it is possible to selectively detect and measure specific metal ions based on their affinity for the crown ether cavity.
Drug delivery systems: The ability of 18-Crown-6 to form complexes with metal ions can be utilized in drug delivery systems. By encapsulating metal ions within the crown ether cavity, it is possible to protect the metal ions during transport and release them in a controlled manner at the target site.
Overall, 18-Crown-6 is a versatile compound that finds applications in phase transfer catalysis, metal ion extraction, ion recognition, and drug delivery. Its unique crown ether structure and complexation properties make it a valuable tool in various fields of chemistry and materials science.
