33089-37-1

Basic information

• Product Name: 1,4,7,10,13,16,19,22-OCTAOXACYCLOTETRACOSANE
• Synonyms: 24-Crown-8;Brn 1686140;Einecs 251-374-9;24-CROWN 8-ETHER;1,4,7,10,13,16,19,22-OCTAOXACYCLOTETRACOSANE
• CAS NO: 33089-37-1
• Molecular Formula: C₁₆H₃₂O₈
• Molecular Weight: 352.42
• EINECS: 251-374-9
• Product Categories: Crown Ethers;Functional Materials;Macrocycles for Host-Guest Chemistry
• Mol File: 33089-37-1.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 497.6 °C at 760 mmHg
• Flash Point: 202.8 °C
• Appearance: /
• Density: 0.995 g/cm³
• Vapor Pressure: 2.18E-09mmHg at 25°C
• Refractive Index: 1.404
• CAS DataBase Reference: 1,4,7,10,13,16,19,22-OCTAOXACYCLOTETRACOSANE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4,7,10,13,16,19,22-OCTAOXACYCLOTETRACOSANE(33089-37-1)
• EPA Substance Registry System: 1,4,7,10,13,16,19,22-OCTAOXACYCLOTETRACOSANE(33089-37-1)

Safety Data

• Statements: 20/21/22
• Safety Statements: 36/37/39
• RTECS: RH1670000
• Hazardous Substances Data: 33089-37-1(Hazardous Substances Data)

Usage

General Description

1,4,7,10,13,16,19,22-Octaoxacyclotetracosane, also known as crown-8, is a cyclic compound consisting of eight oxygen atoms arranged in a ring structure. It is commonly used as a ligand in coordination chemistry due to its ability to complex with various metal ions. The compound is also known for its high stability and solubility in a wide range of solvents, making it a versatile chemical for various applications. Crown-8 has been studied for its potential use in drug delivery systems and as a carrier for ion-selective electrodes. Additionally, it has been investigated for its ability to form supramolecular complexes with other molecules, offering potential applications in materials science and nanotechnology.

InChI:InChI=1/C16H32O8/c1-2-17-4-5-18-6-7-19-8-9-20-10-11-21-12-13-22-14-15-24-16-23-3-1/h1-16H2

Upstream product

• 37860-51-8 tetraethylene glycol di(p-toluenesulfonate) 
• 112-60-7 Tetraethylene glycol 
• 5117-19-1 octaethylene glycol 
• 111-46-6 diethylene glycol 
• 112-27-6 2,2'-[1,2-ethanediylbis(oxy)]bisethanol 

Downstream Products

• 1226919-77-2 CH₂O₃*C₁₆H₃₂O₈*C₄₅H₃₈N₂ 

Relevant articles and documents

Improved preparation of 24-crown-8

An improved method for the preparation of 24-crown-8 is described. Cyclization at room temperature and purification of the crude product via an acetonitrile complex provides a much higher yield than those reported in the literature.

Synthesis of a molecular charm bracelet via click cyclization and olefin metathesis clipping

We describe the synthesis of a polycatenated cyclic polymer, a structure that resembles a molecular charm bracelet. Ruthenium-catalyzed ring-opening metathesis polymerization of an aminocontaining cyclic olefin monomer in the presence of a chain transfer agent generated an α,ω-diazide functionalized polyamine. Cyclization of the resulting linear polyamine using pseudo-high-dilution coppercatalyzed click cyclization produced a cyclic polymer in 19% yield. The click reaction was then further employed to remove linear contaminants from the cyclic polymer using azide- and alkyne-functionalized scavenging resins, and the purified cyclic polymer product was characterized by gel permeation chromatography, 1H NMR spectroscopy, and IR spectroscopy. Polymer hydrogenation and conversion to the corresponding polyammonium species enabled coordination and interlocking of diolefin polyether fragments around the cyclic polymer backbone using ruthenium-catalyzed ring-closing olefin metathesis to afford a molecular charm bracelet structure. This charm bracelet complex was characterized by 1H NMR spectroscopy, and the catenated nature of the small rings was confirmed using two-dimensional diffusionordered NMR spectroscopy.

TEMPLATE EFFECTS. 7. LARGE UNSUBSTITUTED CROWN ETHERS FROM POLYETHYLENE GLYCOLS: FORMATION, ANALYSIS, AND PURIFICATION

Through the reaction of polyethylene glycols with tosyl chloride and heterogeneous KOH in dioxane not only coronands from crown-4 to crown-8 can be obtained but also larger homologues.A systematic investigation has shown that: i) crown-9 and crown-10 can be formed from nona- and deca-ethylene glycol, respectively, and isolated in pure form; ii) the whole series of polyethylene glycols from tri- to deca-ethylene glycol yields not only the corresponding crown ethers but also higher cyclooligomers that can be analyzed up to about crown-20 by glc: in particular crown-12 and crown-16 were obtained from tetraethylene glycol and purified by column chromatography on cellulose; iii) the reaction, as applied to commercial mixtures of polyethylene glycols (from PEG 200 to PEG 1000), gives fairly high yields of crown ethers also in the region of large ring sizes.The contribution of the template effect of K(+) ion and the cyclooligomerization reactions for the various ring sizes are discussed.