3,7-Dibromo-5,5-dimethyl-5H-dibenzo[b,d]silole

Base Information

• Chemical Name: 3,7-Dibromo-5,5-dimethyl-5H-dibenzo[b,d]silole
• CAS No.: 1228595-79-6
• Molecular Formula: C14H12Br2Si
• Molecular Weight: 368.143
• Mol file: 1228595-79-6.mol

Synonyms:3,7-Dibromo-5,5-dimethyl-5H-dibenzo[b,d]silole;3,8-dibromo-1,1-dimethyl-1H-dibenzo[b,d]silole;9H-9-Silafluorene, 2,7-dibromo-9,9-dimethyl-

Chemical Property of 3,7-Dibromo-5,5-dimethyl-5H-dibenzo[b,d]silole

Chemical Property:

• Boiling Point: 396.5±42.0 °C(Predicted)
• PSA: 0.00000
• Density: 1.63±0.1 g/cm3(Predicted)
• LogP: 4.01460
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

98.5% ^*data from raw suppliers

3,7-Dibromo-5,5-dimethyl-5H-dibenzo[b,d]silole 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,7-Dibromo-5,5-dimethyl-5H-dibenzo[b,d]silole

There total 4 articles about 3,7-Dibromo-5,5-dimethyl-5H-dibenzo[b,d]silole 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: 76.0%

4,4’-dibromo-2,2’-diiodo-1,1’-biphenyl (852138-89-7) + dimethylsilicon dichloride (75-78-5,30107-43-8) → 3,7-dibromo-5,5-dimethyl-5H-dibenzo[b,d]silole (1228595-79-6)

Guidance literature:

4,4’-dibromo-2,2’-diiodo-1,1’-biphenyl; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Inert atmosphere;

dimethylsilicon dichloride; In tetrahydrofuran; hexane; at 20 ℃; for 12h; Reflux;

Reference yield:

4,4′-dibromo-[1,1′-biphenyl]-2,2′-diamine (136630-36-9) → 3,7-dibromo-5,5-dimethyl-5H-dibenzo[b,d]silole (1228595-79-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: hydrogenchloride; sodium nitrite / water / 1 h / 0 - 5 °C

1.2: 6 h / 60 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / 3.5 h / -78 °C

2.2: -78 - 20 °C

With hydrogenchloride; n-butyllithium; sodium nitrite; In tetrahydrofuran; hexane; water;

Reference yield:

1,4-dibromo-2-nitrobenzene (3460-18-2) → 3,7-dibromo-5,5-dimethyl-5H-dibenzo[b,d]silole (1228595-79-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: copper / N,N-dimethyl-formamide / 3 h / 125 °C

2.1: tin; hydrogenchloride / ethanol; water / 2 h / Reflux

3.1: nitrosylsulfuric acid; sulfuric acid / 4 h / 0 °C

3.2: 10 - 20 °C

4.1: tert.-butyl lithium / toluene; diethyl ether / 1.75 h / -78 °C / Inert atmosphere

4.2: 20 °C

With hydrogenchloride; tin; nitrosylsulfuric acid; sulfuric acid; tert.-butyl lithium; copper; In diethyl ether; ethanol; water; N,N-dimethyl-formamide; toluene;

DOI:10.1039/c5tc00382b

upstream raw materials:

4,4’-dibromo-2,2’-diiodo-1,1’-biphenyl

dimethylsilicon dichloride

4,4′-dibromo-[1,1′-biphenyl]-2,2′-diamine

1,4-dibromo-2-nitrobenzene

Downstream raw materials:

C₂₀H₁₇NO₂Si

Refernces

• 1、 Song, Jinsheng,Du, Chun,Li, Cuihong,Bo, Zhishan. "Silole-containing polymers for high-efficiency polymer solar cells". . p. 4267 - 4274. Retrieved 2011.
• 2、 Auvray, Marie,Bolze, Frédéric,Clavier, Gilles,Mahuteau-Betzer, Florence. "Silafluorene as a promising core for cell-permeant, highly bright and two-photon excitable fluorescent probes for live-cell imaging". . . Retrieved 2021.
• 3、 -. "Organic light-emitting device". Page/Page column 187; 189. . Retrieved 2021/07/08.