Indeno[1,2-b]fluorene-6,12-dione, 2,8-dibromo-

Base Information

• Chemical Name: Indeno[1,2-b]fluorene-6,12-dione, 2,8-dibromo-
• CAS No.: 853234-57-8
• Molecular Formula: C20H8Br2O2
• Molecular Weight: 440.09
• Mol file: 853234-57-8.mol

Synonyms:2,8-dibromo-indeno[1,2-b]fluorene-6,12-dione;3,9-dibromo-indenofluorenedione;Indeno[1,2-b]fluorene-6,12-dione,2,8-dibromo;

Chemical Property of Indeno[1,2-b]fluorene-6,12-dione, 2,8-dibromo-

Chemical Property:

• Boiling Point: 634.0±55.0 °C(Predicted)
• PSA: 34.14000
• Density: 1.892±0.06 g/cm3(Predicted)
• LogP: 5.42040
• Storage Temp.: Sealed in dry,Room Temperature

Purity/Quality:

98%,99%, ^*data from raw suppliers

2,8-Dibromoindeno[1,2-b]fluorene-6,12-dione >98.0%(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Indeno[1,2-b]fluorene-6,12-dione, 2,8-dibromo-

There total 8 articles about Indeno[1,2-b]fluorene-6,12-dione, 2,8-dibromo- 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: 92.0%

4,4-dibromo-[1,1;4',1]terphenyl-2,2-dicarboxylic acid dimethyl ester (1040516-00-4) → 2,8-dibromo-indeno[1,2-b]fluorene-6,12-dione (853234-57-8)

Guidance literature:

With sulfuric acid; In water; at 120 ℃; for 10h; Acidic aqueous solution;

Reference yield:

benzene-1,4-diboronic acid bispinacol ester (99770-93-1) → 2,8-dibromo-indeno[1,2-b]fluorene-6,12-dione (853234-57-8)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / toluene; water / 48 h / Inert atmosphere; Reflux

2: sulfuric acid / water / 17 h / 120 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sulfuric acid; sodium carbonate; In water; toluene; 1: |Suzuki Coupling / 2: |Friedel-Crafts Acylation;

DOI:10.1039/c5ra22359h

Reference yield:

5-bromo-2-iodo-benzoic acid methyl ester (181765-86-6) → 2,8-dibromo-indeno[1,2-b]fluorene-6,12-dione (853234-57-8)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / toluene; water / 48 h / Inert atmosphere; Reflux

2: sulfuric acid / water / 17 h / 120 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sulfuric acid; sodium carbonate; In water; toluene; 1: |Suzuki Coupling / 2: |Friedel-Crafts Acylation;

DOI:10.1039/c5ra22359h

upstream raw materials:

4,4''-dibromo-[1,1';4',1'']terphenyl-2',5'-dicarboxylic acid

4,4″-dibromo-2′,5′-dimethyl-1,1′:4′,1″-terphenyl

1,4-bromoiodobenzene

1,4-dimethyl-2,5-di(4’,4’,5’,5’-tetramethyl[1,3,2’]dioxaborolan-2’-yl)benzene

Downstream raw materials:

C₃₂H₁₈O₂

C₅₈H₅₈F₁₂O₂Si₂

C₃₆H₁₄F₁₂O₂

C₃₄H₁₄F₈O₂

Refernces

• 1、 Ozdemir, Mehmet,Choi, Donghee,Kwon, Guhyun,Zorlu, Yunus,Kim, Hyekyoung,Kim, Myung-Gil,Seo, SungYong,Sen, Unal,Citir, Murat,Kim, Choongik,Usta, Hakan. "Design, synthesis, and characterization of α,ω-disubstituted indeno[1,2-b]fluorene-6,12-dione-thiophene molecular semiconductors. Enhancement of ambipolar charge transport through synthetic tailoring of alkyl substituents". . p. 212 - 226. Retrieved 2016/01/09.
• 2、 Usta, Hakan,Risko, Chad,Wang, Zhiming,Huang, Hui,Deliomeroglu, Murat K.,et al.. "Design, synthesis, and characterization of ladder-type molecules and polymers. air-stable, solution-processable n-channel and ambipolar semiconductors for thin-film transistors via experiment and theory". supporting information; experimental part. p. 5586 - 5608. Retrieved 2009/09/25.