2-bromo-1,4-bis-trimethylsilanylethynyl-benzene

Base Information

• Chemical Name: 2-bromo-1,4-bis-trimethylsilanylethynyl-benzene
• CAS No.: 887603-49-8
• Molecular Formula: C₁₆H₂₁BrSi₂
• Molecular Weight: 349.418
• Mol file: 887603-49-8.mol

Synonyms:2-bromo-1,4-bis-trimethylsilanylethynyl-benzene

Chemical Property of 2-bromo-1,4-bis-trimethylsilanylethynyl-benzene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-bromo-1,4-bis-trimethylsilanylethynyl-benzene

There total 2 articles about 2-bromo-1,4-bis-trimethylsilanylethynyl-benzene 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:

2-Bromo-4-iodoaniline (29632-73-3) → 2-bromo-1,4-bis-trimethylsilanylethynyl-benzene (887603-49-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: BF₃*OEt₂; tBuONO

1.2: 68 percent / NaI / acetonitrile

2.1: 90 percent / Et₃N; Pd(PPh₃(2Cl₂; CuI / tetrahydrofuran

With copper(l) iodide; tert.-butylnitrite; boron trifluoride diethyl etherate; triethylamine; In tetrahydrofuran; 2.1: Sonogashira coupling reaction;

DOI:10.1016/j.tetlet.2007.06.081

Reference yield:

p-aminoiodobenzene (540-37-4) → 2-bromo-1,4-bis-trimethylsilanylethynyl-benzene (887603-49-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 76 percent / NBS; AcOH / CHCl₃ / 20 °C

2.1: boron trifluoride diethyl etherate / diethyl ether / 0.5 h / -30 °C

2.2: tert-butyl nitrite / diethyl ether / 0.5 h / -20 - -10 °C

2.3: sodium iodide / acetonitrile / 2 h / 20 °C

3.1: 88 percent / triethylamine / PdCl₂(PPh₃)2; CuI / tetrahydrofuran / 16 h / 20 °C

With N-Bromosuccinimide; boron trifluoride diethyl etherate; acetic acid; triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In tetrahydrofuran; diethyl ether; chloroform; 3.1: Castro-Stephens-Sonogashira coupling;

DOI:10.1021/ol060445d

Reference yield: 69.0%

2-bromo-1,4-bis-trimethylsilanylethynyl-benzene (887603-49-8) → 1-iodo-2,5-bis(trimethylsilylacetylene)benzene (887603-50-1)

Guidance literature:

2-bromo-1,4-bis-trimethylsilanylethynyl-benzene; With tert.-butyl lithium; In tetrahydrofuran; diethyl ether; pentane; at -78 ℃; for 1.25h;

With 1,2-Diiodoethane; In tetrahydrofuran; diethyl ether; pentane; at -78 - 20 ℃; for 17h;

DOI:10.1021/ol060445d

upstream raw materials:

2-Bromo-4-iodoaniline

p-aminoiodobenzene

Downstream raw materials:

1-iodo-2,5-bis(trimethylsilylacetylene)benzene