2,5-Bis(4-Bromophenyl)-p-xylene

Base Information

• Chemical Name: 2,5-Bis(4-Bromophenyl)-p-xylene
• CAS No.: 853234-55-6
• Molecular Formula: C20H16Br2
• Molecular Weight: 416.155
• Hs Code.: 2903999090
• DSSTox Substance ID: DTXSID20479173
• Nikkaji Number: J2.233.103E
• Wikidata: Q82313118
• Mol file: 853234-55-6.mol

Synonyms:2,5-Bis(4-Bromophenyl)-p-xylene;853234-55-6;4,4''-Dibromo-2',5'-dimethyl-1,1':4',1''-terphenyl;1,4-bis(4-bromophenyl)-2,5-dimethylbenzene;2,5-Di(4-bromophenyl)-1,4-diemthylbenzene;SCHEMBL13779987;DTXSID20479173;MFCD11855950;AKOS015835663;BS-22808;CS-0211835

Chemical Property of 2,5-Bis(4-Bromophenyl)-p-xylene

Chemical Property:

• PSA: 0.00000
• LogP: 7.16240
• XLogP3: 8.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 415.95983
• Heavy Atom Count: 22
• Complexity: 306

Purity/Quality:

95% ^*data from raw suppliers

2,5-Bis(4-Bromophenyl)-p-xylene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=C(C=C1C2=CC=C(C=C2)Br)C)C3=CC=C(C=C3)Br

Technology Process of 2,5-Bis(4-Bromophenyl)-p-xylene

There total 2 articles about 2,5-Bis(4-Bromophenyl)-p-xylene 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%

1,4-bromoiodobenzene (589-87-7) + 1,4-dimethyl-2,5-di(4’,4’,5’,5’-tetramethyl[1,3,2’]dioxaborolan-2’-yl)benzene (303006-89-5) → 4,4″-dibromo-2′,5′-dimethyl-1,1′:4′,1″-terphenyl (853234-55-6)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In tetrahydrofuran; for 6h; Heating;

DOI:10.1021/ol051661+

Reference yield:

2,5-dibromo-p-xylene (1074-24-4) → 4,4″-dibromo-2′,5′-dimethyl-1,1′:4′,1″-terphenyl (853234-55-6)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 12 h / 170 °C / Inert atmosphere; Schlenk technique; Glovebox

2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / tetrahydrofuran; water / 72 h / 75 °C / Inert atmosphere; Schlenk technique; Glovebox

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium acetate; potassium carbonate; In tetrahydrofuran; water; N,N-dimethyl-formamide;

DOI:10.1039/c9cc07729d

Reference yield: 78.0%

4,4″-dibromo-2′,5′-dimethyl-1,1′:4′,1″-terphenyl (853234-55-6) + N-(4-(tert-butyl)phenyl)-[1,1′-biphenyl]-4-amine (950917-84-7) → N4,N4″-di([1,1′-biphenyl]-4-yl)-N4,N4″-bis(4-(tert-butyl)phenyl)-2′,5′-dimethyl-[1,1′:4′,1″-terphenyl]-4,4″-diamine

Guidance literature:

With tri-tert-butyl phosphine; potassium tert-butylate; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In toluene; at 80 ℃; for 22.5h; Inert atmosphere;

upstream raw materials:

1,4-bromoiodobenzene

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

2,5-dibromo-p-xylene

Downstream raw materials:

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

Refernces

• 1、 Vak, Doojin,Lim, Bogyu,Lee, Soo-Hyoung,Kim, Dong-Yu. "Synthesis of a double spiro-polyindenofluorene with a stable blue emission". . p. 4229 - 4232. Retrieved 2007/10/03.