1,1,2,3,4,5-Hexaphenylsilole

Base Information

• Chemical Name: 1,1,2,3,4,5-Hexaphenylsilole
• CAS No.: 752-28-3
• Molecular Formula: C40H30Si
• Molecular Weight: 538.764
• Mol file: 752-28-3.mol

Synonyms:1,1,2,3,4,5-hexakis-phenylsilole;

Chemical Property of 1,1,2,3,4,5-Hexaphenylsilole

Chemical Property:

• Melting Point: 193.0 to 197.0 °C
• Boiling Point: 674.1±55.0 °C(Predicted)
• PSA: 0.00000
• Density: 1.18±0.1 g/cm3(Predicted)
• LogP: 8.56360

Purity/Quality:

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

1,1,2,3,4,5-Hexaphenylsilole >98.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Hexaphenylsilacyclopentadiene may undergo π4s+π2s cycloaddition with ethyl acrylate to form bicyclosilaheptene. The same study reports similar cycloaddition reactions with various dienophiles. The reaction of hexaphenylsilacyclopentadiene with perbenzoic acid yields a mixture of tetraphenylfuran and cis-dibenzoylstilbene.

Technology Process of 1,1,2,3,4,5-Hexaphenylsilole

There total 7 articles about 1,1,2,3,4,5-Hexaphenylsilole 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%

diphenyl acetylene (501-65-5) + diphenylsilyl dichloride (80-10-4) → hexaphenylsilole (752-28-3)

Guidance literature:

diphenyl acetylene; With lithium; at 20 ℃; for 5h; Inert atmosphere;

diphenylsilyl dichloride; for 4h;

DOI:10.1002/anie.201814507

Reference yield: 25.0%

1-chloro-1,2,3,4,5-pentaphenyl-1-silacyclopentadiene (16030-07-2) + methyl iodide (74-88-4) → 1,2,3,4,5-pentaphenyl-1-methylsilole (7641-42-1) + hexaphenylsilole (752-28-3) + 1,1-dimethyl-2,3,4,5-tetraphenylsilole (7641-40-9)

Guidance literature:

1-chloro-1,2,3,4,5-pentaphenyl-1-silacyclopentadiene; With lithium; In tetrahydrofuran; at -78 - 20 ℃;

methyl iodide; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1016/j.jorganchem.2003.09.040

Reference yield:

diphenylsilyl dichloride (80-10-4) → hexaphenylsilole (752-28-3)

Guidance literature:

With tetrahydrofuran; diethyl ether;

DOI:10.1021/ja01482a026

upstream raw materials:

diphenyl acetylene

diphenylsilyl dichloride

1-chloro-1,2,3,4,5-pentaphenyl-1-silacyclopentadiene

methyl iodide

Downstream raw materials:

1,4,5,6,7,7-hexaphenyl-7-sila-bicyclo[2.2.1]hept-5-ene-2endo,3endo-dicarboxylic acid anhydride

1,2,3,4,9,9-hexaphenyl-1,4-dihydro-1,4-episilano-naphthalene

1,4,5,6,7,7-hexaphenyl-7-sila-bicyclo[2.2.1]hept-5-ene-2endo-carbonitrile

1,4,5,6,7,7-hexaphenyl-7-sila-bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic acid dimethyl ester

Refernces

• 1、 Han, Zhengang,Yang, Zhaofan,Sun, Heshui,Xu, Yali,Ma, Xiaofang,Shan, Duoliang,Chen, Jing,Huo, Shuhui,Zhang, Zhen,Du, Peiyao,Lu, Xiaoquan. "Electrochemiluminescence Platforms Based on Small Water-Insoluble Organic Molecules for Ultrasensitive Aqueous-Phase Detection". supporting information. p. 5915 - 5919. Retrieved 2019/04/03.
• 2、 Ren, Yan,Lam, Jackv W. Y.,Dong, Yongqiang,Tang, Ben Zhong,Wong, Kam Sing. "Enhanced emission efficiency and excited state lifetime due to restricted intramolecular motion in silole aggregates". . p. 1135 - 1140. Retrieved 2007/10/03.