Tetraphenylnaphthacene monoxide

Base Information

• Chemical Name: Tetraphenylnaphthacene monoxide
• CAS No.: 127257-80-1
• Molecular Formula: C42H28 O
• Molecular Weight: 548.684
• DSSTox Substance ID: DTXSID50925830
• Nikkaji Number: J2.942.372E
• Mol file: 127257-80-1.mol

Synonyms:Tetraphenylnaphthacene monoxide;127257-80-1;DTXSID50925830;5,6,11,12-tetraphenyl-5,12-dihydro-5,12-epoxytetracene

Chemical Property of Tetraphenylnaphthacene monoxide

Chemical Property:

• Density: 1.251g/cm³
• XLogP3: 10.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 548.214015512
• Heavy Atom Count: 43
• Complexity: 872

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=C3C(=C(C4=CC=CC=C42)C5=CC=CC=C5)C6(C7=CC=CC=C7C3(O6)C8=CC=CC=C8)C9=CC=CC=C9

Technology Process of Tetraphenylnaphthacene monoxide

There total 15 articles about Tetraphenylnaphthacene monoxide 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: 99.0%

1,3-diphenylisobenzofuran (5471-63-6) + 2,3-dibromo-1,4-diphenylnaphthalene (127257-79-8) → 5,12-dihydro-5,12-epoxy-5,6,11,12-tetraphenylnaphthacene (127257-80-1)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; -78 deg C -> room temp., 12h;

DOI:10.1021/jo00300a043

Reference yield: 83.0%

1,3-diphenylisobenzofuran (5471-63-6) + 2,3-diiodo-1,4-diphenylnaphthalene → 5,12-dihydro-5,12-epoxy-5,6,11,12-tetraphenylnaphthacene (127257-80-1)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -78 - 20 ℃; for 12h;

DOI:10.1016/j.tet.2011.08.084

Reference yield:

1,3-diphenylisobenzofuran (5471-63-6) → 5,12-dihydro-5,12-epoxy-5,6,11,12-tetraphenylnaphthacene (127257-80-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 67 percent / p-toluenesulfonic acid / xylene / 4 h / Heating

2: 99 percent / n-BuLi / tetrahydrofuran; hexane / -78 deg C -> room temp., 12h

With n-butyllithium; toluene-4-sulfonic acid; In tetrahydrofuran; hexane; xylene;

DOI:10.1021/jo00300a043

upstream raw materials:

5,6,11,12-tetraphenylnaphthacene

5r.6.11.12c-tetraphenyl-5.12-dihydro-naphthacenediol-(5.12t)

1,3-diphenylisobenzofuran

2,3-dibromo-1,4-diphenylnaphthalene

Downstream raw materials:

5,6,11,12-tetraphenylnaphthacene

o-dibenzoylbenzene

Refernces

• 1、 Dodge, Jeffrey A.,Bain, J. D.,Chamberlin, A. Richard. "Regioselective Synthesis of Substituted Rubrenes". . p. 4190 - 4198. Retrieved 2007/10/02.