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12-Crown-4

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Identification
Molecular formula
C8H16O4
CAS number
294-92-8
IUPAC name
1,4,7,10-tetraoxacyclododecane
State
State
12-Crown-4 can exist as a liquid or solid at room temperature, with its state depending largely on purity and ambient conditions. It is often encountered as a liquid because of its low melting point.
Melting point (Celsius)
2.00
Melting point (Kelvin)
275.15
Boiling point (Celsius)
232.00
Boiling point (Kelvin)
505.00
General information
Molecular weight
176.21g/mol
Molar mass
176.2110g/mol
Density
1.2460g/cm3
Appearence

12-Crown-4 is a colorless liquid or a low melting solid, depending on the purity and ambient temperature. It is typically waxy or oily in its solid form and usually clear when in liquid form.

Comment on solubility

Solubility of 1,4,7,10-Tetraoxacyclododecane

1,4,7,10-Tetraoxacyclododecane, also known as crown ether, exhibits interesting solubility characteristics that stem from its unique molecular structure.

This compound is known for its ability to solvate various cations due to the presence of its ether oxygen atoms that can interact with positively charged ions. Some key points regarding its solubility include:

  • Solvent Compatibility: It is generally soluble in polar organic solvents such as methanol, ethanol, and acetone.
  • Water Solubility: It is slightly soluble in water, primarily due to its bulky structure that hinders full hydration of the molecule.
  • Ionic Interaction: Its solubility in organic solvents helps to facilitate interactions with metal ions, enhancing its utility in complexation and extraction processes.

In summary, the solubility of 1,4,7,10-tetraoxacyclododecane is influenced by its ether functional groups, allowing it to engage in complexation with various cations, while its bulkier structure limits its solubility in aqueous environments. This characteristic makes it valuable in both synthetic and analytical chemistry.

Interesting facts

Exploring 1,4,7,10-Tetraoxacyclododecane

1,4,7,10-Tetraoxacyclododecane, also known as crown ether, is a versatile cyclic compound in organic chemistry. This unique molecule contains four ether linkages, which result in a highly symmetrical structure. Here are some intriguing points about this compound:

  • Structural Unique: The cyclic nature of 1,4,7,10-tetraoxacyclododecane allows for a large central cavity that can encapsulate cations, making it an excellent host molecule in supramolecular chemistry.
  • Selectivity: This compound exhibits remarkable selectivity towards certain metal ions, particularly alkaline metals like Li+, Na+, and K+. This property can be leveraged for ion extraction and separation processes.
  • Applications: Due to its ability to selectively bind ions, it finds applications in various fields, including:
    • Analytical Chemistry: Used in ion-selective electrodes and sensors.
    • Nanotechnology: Plays a role in the design of nanoscale devices.
    • Drug Delivery: Investigated for its potential in targeted drug delivery systems.
  • Historical Significance: Crown ethers, including 1,4,7,10-tetraoxacyclododecane, have spurred extensive research since their discovery, leading to numerous studies and the development of new materials.
  • Complex Formation: The ability to form stable complexes with metal ions results in distinctive color changes, making these compounds visually appealing and easy to study in solution.

In the world of chemistry, 1,4,7,10-tetraoxacyclododecane stands out not only for its structural elegance but also for its practical utility. Its role in facilitating ion transport and selectivity makes it a subject of ongoing research and application in innovative materials science.

Synonyms
12-Crown-4
294-93-9
1,4,7,10-TETRAOXACYCLODODECANE
EOCT
12-Crown-4 ether
Ethylene oxide cyclic tetramer
12-crown-4-ether
CCRIS 157
MFCD00005103
EINECS 206-036-5
UNII-K6069P2C2A
BRN 1363064
12-Crown 4-Ether
DTXSID6059780
CHEBI:32399
XQQZRZQVBFHBHL-UHFFFAOYSA-
K6069P2C2A
5-19-11-00334 (Beilstein Handbook Reference)
12-Crown-4-ether12C4Ethylene oxide cyclic tetramer
SCHEMBL236725
CHEMBL4566196
DTXCID2037978
3,6,9,12-tetraoxacyclododecan
1,4,7,10tetraoxa-Cyclododecane
1,4,7,10-tetraoxacyclo-dodecane
AKOS015907759
LS-13523
SY048391
NS00028718
D89315
A819938
Q4261972
12-Crown-4, Cyclic tetramer of ethylene oxide which is specific for the lithium cation., 98%
206-036-5