Rubicene

Base Information

• Chemical Name: Rubicene
• CAS No.: 197-61-5
• Molecular Formula: C26H14
• Molecular Weight: 326.397
• Hs Code.: 29029000
• European Community (EC) Number: 205-899-5
• NSC Number: 87524
• UNII: J3I9M3715F
• DSSTox Substance ID: DTXSID00173364
• Nikkaji Number: J193.674C
• Wikipedia: Rubicene
• Wikidata: Q27115550
• Metabolomics Workbench ID: 54816
• Mol file: 197-61-5.mol

Synonyms:Rubicene;197-61-5;Rubicene-;rubicen;UNII-J3I9M3715F;J3I9M3715F;EINECS 205-899-5;NSC 87524;NSC-87524;NSC87524;CHEBI:33095;DTXSID00173364;AKOS025213928;Q27115550

Chemical Property of Rubicene

Chemical Property:

• Vapor Pressure: 8.5E-13mmHg at 25°C
• Melting Point: 305 °C
• Refractive Index: 1.8430 (estimate)
• Boiling Point: 579°Cat760mmHg
• Flash Point: 298.8°C
• PSA: 0.00000
• Density: 1.391g/cm³
• LogP: 7.48140
• XLogP3: 7.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 326.109550447
• Heavy Atom Count: 26
• Complexity: 514

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C3=C4C2=C5C=CC=C6C5=C(C4=CC=C3)C7=CC=CC=C76

Technology Process of Rubicene

There total 23 articles about Rubicene 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: 80.0%

9,10-diphenylanthracene (1499-10-1) → rubicene (197-61-5)

Guidance literature:

With trifluorormethanesulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 0 ℃; for 0.166667h; Inert atmosphere;

DOI:10.1055/s-0036-1588570

Reference yield: 49.0%

9,10-bis-(2-fluorophenyl)-anthracene (956336-68-8) → rubicene (197-61-5)

Guidance literature:

With dimethyldimesitylsilane; In chlorobenzene; at 110 ℃; Inert atmosphere;

DOI:10.1126/science.1202432

Reference yield: 38.0%

9-(9'H-fluoren-9'-ylidene)-9H-xanthene (27090-15-9) → 9H-xanthene-9-thione (492-21-7) + tetrabenzo[5.5]fulvalene (746-47-4) + rubicene (197-61-5)

Guidance literature:

With sulfur; at 270 - 280 ℃; for 0.0833333h;

upstream raw materials:

9H-fluorene

9-fluorenone

diphenic acid

1,5-dichloro-9,10-diphenyl-9,10-dihydroanthracene-9,10-diol

Refernces

• 1、 Kawamura, Masahiko,Tsurumaki, Eiji,Toyota, Shinji. "Facile Synthesis of Rubicenes by Scholl Reaction". . p. 134 - 138. Retrieved 2018.
• 2、 Jackson, Edward A.,Xue, Xiang,Cho, Hee Yeon,Scott, Lawrence T.. "Probing mechanisms of aryl-aryl bond cleavages under flash vacuum pyrolysis conditions". . p. 1279 - 1287. Retrieved 2014/11/08.