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:

98%,99%, ^*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:

[Rh(2,3,7,8,12,13,17,18-octaethylporphyrin)Cl(C₅H₄NCH₂NH₂CH₂C₆H₄CMe₃)](CF₃COO)*(dibenzo-24-crown-8)

[3,5-dimethylphenyl-CH₂NH₂CH₂C₆H₄CCH-dicobalt hexacarbonyl](hexafluorophosphate)*dibenzo[24]crown8

[9-anthryl-CH₂NH₂CH₂C₆H₄CC-phenyl-dicobalt hexacarbonyl](hexafluorophosphate)*dibenzo[24]crown8

Refernces

• 1、 Tawarah, K. M.,Mizyed, S. A.. "A Conductance Study of the Association of Alkali Cations with 1,13-Dibenzo-24-Crown-8 in Acetonitrile". . p. 387 - 402. Retrieved 1989.
• 2、 Wessels, Hanlie R.,Gibson, Harry W.. "Multi-gram syntheses of four crown ethers using K+ as templating agent". . p. 396 - 399. Retrieved 2016.
• 3、 Tachibana, Yuya,Kihara, Nobuhiro,Furusho, Yoshio,Takata, Toshikazu. "Is the tert-butyl group bulky enough to end-cap a pseudorotaxane with a 24-crown-8-ether wheel?". . p. 4507 - 4509. Retrieved 2004.
• 4、 Coutrot, Frédéric,Gauthier, Maxime. "Discrepancy Regarding the Dethreading of a Dibenzo-24-crown-8 Macrocycle through a Perfluorobutyl End in [2]Pseudorotaxanes". supporting information. . Retrieved 2021/10/23.