Benzo[b]triphenylene-9,14-dione

Base Information

• Chemical Name: Benzo[b]triphenylene-9,14-dione
• CAS No.: 3228-74-8
• Molecular Formula: C₂₂H₁₂O₂
• Molecular Weight: 308.336
• NSC Number: 30839
• DSSTox Substance ID: DTXSID50283301
• Nikkaji Number: J1.494.636E
• Wikidata: Q82017821
• Mol file: 3228-74-8.mol

Synonyms:3228-74-8;benzo[b]triphenylene-9,14-dione;benzo[f]tetraphene-9,14-dione;NSC30839;SCHEMBL5850565;DTXSID50283301;NSC-30839

Chemical Property of Benzo[b]triphenylene-9,14-dione

Chemical Property:

• Vapor Pressure: 1.82E-12mmHg at 25°C
• XLogP3: 5.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 308.083729621
• Heavy Atom Count: 24
• Complexity: 490

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C3=CC=CC=C3C4=C2C(=O)C5=CC=CC=C5C4=O

Technology Process of Benzo[b]triphenylene-9,14-dione

There total 2 articles about Benzo[b]triphenylene-9,14-dione 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: 74.0%

2-(trimethylsilyl)phenyl trifluoromethanesulfonate (88284-48-4) + 2-benzylidene-indan-1,3-dione (5381-33-9) → dibenzanthracene-9,14-dione (3228-74-8) + (E)-11-benzylidene-5H-dibenzo[a,d][7]annulene-5,10(11H)-dione

Guidance literature:

With potassium fluoride; 18-crown-6 ether; In acetonitrile; at 25 ℃; for 16h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;

DOI:10.1039/c9ob01900f

Reference yield: 52.0%

2-ethynyl-1,1'-biphenyl (52889-62-0) → dibenzanthracene-9,14-dione (3228-74-8) + 2-methoxy-2-phenyl-1-oxa-cyclopenta[l]phenanthren-3-one

Guidance literature:

2-ethynyl-1,1'-biphenyl; (CH₃O)(C₆H₅)C=Cr(CO)5; In 1,4-dioxane; at 100 ℃; for 24h;

With air; silica gel; In hexane; ethyl acetate;

DOI:10.1016/S0040-4020(01)00227-7

Reference yield: 45.0%

dibenzanthracene-9,14-dione (3228-74-8) → dibenzo[a,c]anthracene (215-58-7)

Guidance literature:

With Al(c-C₆H₁₁O)3; in cyclohexanol;

DOI:10.1021/ja00524a059

upstream raw materials:

2-ethynyl-1,1'-biphenyl

2-(trimethylsilyl)phenyl trifluoromethanesulfonate

2-benzylidene-indan-1,3-dione

Downstream raw materials:

dibenzo[a,c]anthracene

Refernces

• 1、 Jackson, Thaddeus J,Herndon, James W. "Annulation selectivity in the coupling of Fischer carbene complexes with o-alkynylbiphenyl and o-alkynylstyrene derivatives". . p. 3859 - 3868. Retrieved 2007/10/03.