9H,9'H-3,3'-Bicarbazole

Base Information

• Chemical Name: 9H,9'H-3,3'-Bicarbazole
• CAS No.: 1984-49-2
• Molecular Formula: C24H16N2
• Molecular Weight: 332.404
• Hs Code.: 2933990090
• European Community (EC) Number: 807-984-8
• DSSTox Substance ID: DTXSID30499226
• Nikkaji Number: J2.381.869H
• Wikidata: Q72443373
• Mol file: 1984-49-2.mol

Synonyms:9H,9'H-3,3'-Bicarbazole;1984-49-2;3,3'-Bicarbazole;3-(9H-carbazol-3-yl)-9H-carbazole;3,3'-BI-9H-CARBAZOLE;MFCD11046470;SCHEMBL670060;DTXSID30499226;PUMOFXXLEABBTC-UHFFFAOYSA-N;AKOS015911953;AM84677;SB66604;AC-24435;AS-10022;SY055481;3,3 inverted exclamation mark -Bicarbazole;B4646;CS-0020095;9H,9'H-3,3'-bicarbazole;A851626

Chemical Property of 9H,9'H-3,3'-Bicarbazole

Chemical Property:

• Appearance/Colour: white to off-white powder
• Melting Point: 365 °C
• Boiling Point: 656.033 °C at 760 mmHg
• PKA: 16.79±0.30(Predicted)
• Flash Point: 307.71 °C
• PSA: 31.58000
• Density: 1.341 g/cm³
• LogP: 6.62260
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 6.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 332.131348519
• Heavy Atom Count: 26
• Complexity: 472

Purity/Quality:

99% ^*data from raw suppliers

3,3'-Bicarbazole >98.0%(HPLC)(N) ^*data from reagent suppliers

Safty Information:

• Statements: 36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C3=C(N2)C=CC(=C3)C4=CC5=C(C=C4)NC6=CC=CC=C65
• Uses: 3,3'-bicarbazole can be used to synthesize liquid crystal materials.

Technology Process of 9H,9'H-3,3'-Bicarbazole

There total 6 articles about 9H,9'H-3,3'-Bicarbazole 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: 93.0%

9H-carbazole (86-74-8,105184-46-1,97960-57-1) → 9H,9′H-[3,3′]bicarbazole (1984-49-2)

Guidance literature:

9H-carbazole; With methanesulfonic acid; In dichloromethane; at 0 ℃; Inert atmosphere;

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 20 ℃; for 0.0166667h; Reagent/catalyst; regioselective reaction; Inert atmosphere;

DOI:10.1021/acs.joc.8b02322

Reference yield: 72.2%

3-bromo-9H-carbazole (1592-95-6) + 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 9H-carbazole (855738-89-5) → 9H,9′H-[3,3′]bicarbazole (1984-49-2)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In ethanol; water; toluene; at 78 ℃; Inert atmosphere;

DOI:10.1016/j.jphotochem.2019.112178

Reference yield: 67.0%

N4,N4'-bis(2-bromophenyl)biphenyl-4,4'-diamine (1160823-44-8) → 9H,9′H-[3,3′]bicarbazole (1984-49-2)

Guidance literature:

With potassium tert-butylate; In dimethyl sulfoxide; for 1.5h; UV-irradiation;

DOI:10.1021/jo9006249

upstream raw materials:

9H-carbazole

N₄,N₄'-bis(2-bromophenyl)biphenyl-4,4'-diamine

3-bromo-9H-carbazole

9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-9H-carbazole

Downstream raw materials:

9-phenyl-3,3'-bicarbazole

9-(4,6-diphenyl-1,3,5-triazin-2-yl)-9'-phenyl-3,3'-bicarbazole

C₄₆H₃₀N₄

9-(1,1'-biphenyl)-4-yl-3,3'-bicarbazole

Refernces

• 1、 Vaitkeviciene,Grazulevicius,Jankauskas. "3,3'-Bicarbazolyl-containing oxirane and its reaction products as new glass-forming electroactive materials". . p. 241/[573]-253/[585]. Retrieved 2008.
• 2、 Kim, Jungwoon,Lee, Suhan,Lee, Jaemin,Lim, Eunhee,Jung, Byung Jun. "3,3-Bicarbazole-Based Host Molecules for Solution-Processed Phosphorescent OLEDs". . . Retrieved 2018.
• 3、 Mallick, Sudesh,Maddala, Sudhakar,Kollimalayan, Kalidass,Venkatakrishnan, Parthasarathy. "Oxidative Coupling of Carbazoles: A Substituent-Governed Regioselectivity Profile". . p. 73 - 93. Retrieved 2019/01/10.