Dibenzo-24-crown-8

Base Information

• Chemical Name: Dibenzo-24-crown-8
• CAS No.: 14174-09-5
• Molecular Formula: C24H32 O8
• Molecular Weight: 448.513
• Hs Code.: 29329995
• European Community (EC) Number: 238-027-7
• NSC Number: 244972
• DSSTox Substance ID: DTXSID50161817
• Nikkaji Number: J151.278A
• Wikidata: Q72463450
• ChEMBL ID: CHEMBL154420
• Mol file: 14174-09-5.mol

Synonyms:6,7,9,10,12,12,20,21,23,24,26,27-dodecahydrodibenzo(b,n)-(1,4,7,10,13,16,19,22)octaoxacyclotetracosin;dibenzo(24)crown-8;dibenzo-24-crown-8

Chemical Property of Dibenzo-24-crown-8

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 2.42E-13mmHg at 25°C
• Melting Point: 103 - 105 C
• Refractive Index: 1.5500 (estimate)
• Boiling Point: 591.5 °C at 760 mmHg
• Flash Point: 235.5 °C
• PSA: 73.84000
• Density: 1.084 g/cm³
• LogP: 2.98200
• Storage Temp.: Store below +30°C.
• Sensitive.: air sensitive
• Solubility.: almost transparency in hot Methanol
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 0
• Exact Mass: 448.20971797
• Heavy Atom Count: 32
• Complexity: 372

Purity/Quality:

97% ^*data from raw suppliers

Dibenzo-24-crown-8 ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Other Organic Compounds
• Canonical SMILES: C1COCCOC2=CC=CC=C2OCCOCCOCCOC3=CC=CC=C3OCCO1

Technology Process of Dibenzo-24-crown-8

There total 52 articles about Dibenzo-24-crown-8 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

C26H29NO2*C24H32O8*F6P(1-)*H(1+) → dibenzo-24-crown ether (14174-09-5)

Guidance literature:

With tetra(n-butyl)ammonium hydroxide; In dimethylsulfoxide-d6; water; at 20 ℃; for 3h;

DOI:10.1002/chem.201000968

Reference yield: 87.0%

benzene-1,2-diol (120-80-9,19481-10-8,37349-32-9) + 1,2-bis{2-[2-(2-tosylethoxy)ethoxy]ethoxy}benzene (240797-46-0) → dibenzo-24-crown ether (14174-09-5)

Guidance literature:

With potassium hexafluorophosphate; potassium carbonate; In acetonitrile; for 72h; Inert atmosphere; Reflux; Darkness;

DOI:10.1016/j.tet.2015.11.055

Reference yield: 46.0%

benzene-1,2-diol (120-80-9,19481-10-8,37349-32-9) + 1,8-dichloro-3,6-octanediol → dibenzo-24-crown ether (14174-09-5)

Guidance literature:

With sodium hydroxide; In butan-1-ol; at 105 - 110 ℃; for 20h;

upstream raw materials:

C₂₄H₃₂O₈*Na⁽¹⁺⁾

benzene-1,2-diol

1,2-bis(2-chloroethoxy)ethane

Downstream raw materials:

cis-syn-cis dicyclohexano-24-crown-8

2,5,8,11,18,21,24,27-Octaoxa-tricyclo[26.4.0.0^12,17]dotriaconta-1⁽³²⁾,12⁽¹⁷⁾,13,15,28,30-hexaene; compound with picric acid

m,m'-ditosyldibenzo-24-crown-8

m,m'-ditosyldibenzo-24-crown-8

Refernces

Radically polymerizable pseudorotaxane monomers: Versatile building units for side chain polyrotaxane synthesis

10.1246/cl.1999.111

The research focuses on the synthesis of side chain polyrotaxanes using radically polymerizable pseudorotaxane monomers. The purpose of this study was to develop a versatile method for creating side chain polyrotaxanes, which are supramolecular structures with unique properties due to their mechanical bonding. The researchers utilized secondary ammonium salts with (meth)acrylate groups at one end and bulky stoppers at the other, combined with dibenzo-24-crown-8 (DB24C8), to form pseudorotaxane monomers. Through radical polymerization, they successfully synthesized polymers with rotaxane moieties in the side chains. The conclusions drawn from the study indicate that this method can provide a wide variety of side chain polyrotaxanes with a controlled number of rotaxane units, which can be调节 by varying the polymerization conditions.

Integrative self-sorting: Construction of a cascade-stoppered hetero[3]rotaxane

10.1021/ja806009d

The research describes the construction of a complex supramolecular structure known as a hetero[3]rotaxane through a process called integrative self-sorting. The purpose of this study was to demonstrate how different subunits could be integrated into a single complex with precise positional control, mimicking nature's efficient use of noncovalent self-assembly and self-sorting phenomena. The researchers used two very similar crown ethers, benzo-21-crown-7 (C7) and dibenzo-24-crown-8 (C8), along with two components, 1-H·PF6 and 2-H·PF6, to create a four-component self-sorting system. They then integrated these into a divalent counterpart, 3-2H·2PF6, which has two binding sites. The study concluded that through integrative self-sorting, a well-organized hetero[3]rotaxane structure was successfully constructed, with C7 and C8 binding almost quantitatively to sites A and B, respectively, on the axle 3-2H·2PF6. The researchers also synthesized a "cascade-stoppered" hetero[3]rotaxane, 5-2H·2PF6, which was shown to be highly stable against dethreading of one of the wheels. This research highlights the potential of integrative self-sorting as a programming language in nature for constructing complex supramolecular assemblies and artificial smart materials with well-organized structures and functions.

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