2,5-Dibromo-1,1-dimethyl-3,4-diphenylsilole

Base Information

• Chemical Name: 2,5-Dibromo-1,1-dimethyl-3,4-diphenylsilole
• CAS No.: 686290-22-2
• Molecular Formula: C18H16Br2Si
• Molecular Weight: 420.219
• DSSTox Substance ID: DTXSID70471243
• Nikkaji Number: J2.662.788E
• Wikidata: Q82299712
• Mol file: 686290-22-2.mol

Synonyms:2,5-Dibromo-1,1-dimethyl-3,4-diphenylsilole;686290-22-2;2,5-Dibromo-1,1-dimethyl-3,4-diphenylsilacyclopenta-2,4-diene;2,5-Dibromo-1,1-dimethyl-3,4-diphenyl-1H-silole;DTXSID70471243;MFCD28384141;Silacyclopenta-2,4-diene, 2,5-dibromo-1,1-dimethyl-3,4-diphenyl-;CS-0435382;D4631;T71227

Chemical Property of 2,5-Dibromo-1,1-dimethyl-3,4-diphenylsilole

Chemical Property:

• Melting Point: 162 - 163 °C
• PSA: 0.00000
• LogP: 6.39920
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 419.93675
• Heavy Atom Count: 21
• Complexity: 422

Purity/Quality:

99% ^*data from raw suppliers

2,5-Dibromo-1,1-dimethyl-3,4-diphenylsilacyclopenta-2,4-diene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C[Si]1(C(=C(C(=C1Br)C2=CC=CC=C2)C3=CC=CC=C3)Br)C

Technology Process of 2,5-Dibromo-1,1-dimethyl-3,4-diphenylsilole

There total 2 articles about 2,5-Dibromo-1,1-dimethyl-3,4-diphenylsilole 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: 96.0%

dimethylbis(phenylethynyl)silane (2170-08-3) → 1,1-dimethyl-2,5-dibromo-3,4-diphenylsilole (686290-22-2)

Guidance literature:

dimethylbis(phenylethynyl)silane; With naphthalene; lithium; In tetrahydrofuran; for 0.333333h; Inert atmosphere;

With zinc(II) chloride; In tetrahydrofuran; at -10 - 20 ℃; Inert atmosphere;

With N-Bromosuccinimide; In tetrahydrofuran; at -70 - -50 ℃; for 0.5h; Inert atmosphere;

DOI:10.15227/orgsyn.085.0053

Reference yield:

1,1-dimethyl-3,4-diphenylsilole (55227-55-9) → 1,1-dimethyl-2,5-dibromo-3,4-diphenylsilole (686290-22-2)

Guidance literature:

With N-Bromosuccinimide; Inert atmosphere;

DOI:10.1002/jhet.796

Reference yield: 95.0%

trimethylsilylacetylene (1066-54-2) + 1,1-dimethyl-2,5-dibromo-3,4-diphenylsilole (686290-22-2) → 1,1-di-methyl-3,4-diphenyl-2,5-bis[(trimethylsilyl)ethynyl]silole (1196966-66-1)

Guidance literature:

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triphenylphosphine; In triethylamine; for 8h; Inert atmosphere; Reflux;

DOI:10.1002/anie.200903698

upstream raw materials:

dimethylbis(phenylethynyl)silane

1,1-dimethyl-3,4-diphenylsilole

Downstream raw materials:

1,1-dimethyl-3,4-diphenyl-2,5-bis(4-iodophenylethynyl)silole

2,5-bis[(4-ethynylphenyl)ethynyl]-1,1-dimethyl-3,4-diphenylsilole

1,1-di-methyl-3,4-diphenyl-2,5-bis[(triethylsilyl)ethynyl]silole

1,1-dimethyl-3,4-diphenyl-2,5-bis[(triisopropylsilyl)ethynyl]silole

Refernces

• 1、 Lehrich, Steve W.,Hildebrandt, Alexander,Rüffer, Tobias,Korb, Marcus,Low, Paul J.,Lang, Heinrich. "Synthesis, characterization, electrochemistry, and computational studies of ferrocenyl-substituted siloles". . p. 4836 - 4845. Retrieved 2014.
• 2、 Park, Young Tae. "Grignard metathesis polymerization and properties of 1,1-disubstituted-2,5- dibromo-3,4-diphenylsiloles". . p. 1825 - 1831. Retrieved 2014/07/07.