4,4,5,5-tetramethyl-2-{4-[2-(3,4,5-trimethoxyphenyl)-vinyl]-phenyl}-[1,3,2]dioxaborolane

Base Information

• Chemical Name: 4,4,5,5-tetramethyl-2-{4-[2-(3,4,5-trimethoxyphenyl)-vinyl]-phenyl}-[1,3,2]dioxaborolane
• CAS No.: 1169942-95-3
• Molecular Formula: C₂₃H₂₉BO₅
• Molecular Weight: 396.291
• Mol file: 1169942-95-3.mol

Synonyms:4,4,5,5-tetramethyl-2-{4-[2-(3,4,5-trimethoxyphenyl)-vinyl]-phenyl}-[1,3,2]dioxaborolane

Chemical Property of 4,4,5,5-tetramethyl-2-{4-[2-(3,4,5-trimethoxyphenyl)-vinyl]-phenyl}-[1,3,2]dioxaborolane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4,4,5,5-tetramethyl-2-{4-[2-(3,4,5-trimethoxyphenyl)-vinyl]-phenyl}-[1,3,2]dioxaborolane

There total 4 articles about 4,4,5,5-tetramethyl-2-{4-[2-(3,4,5-trimethoxyphenyl)-vinyl]-phenyl}-[1,3,2]dioxaborolane 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%

triphenyl-(3,4,5-trimethoxybenzyl)phosphonium bromide (61240-20-8) + 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde (128376-64-7) → 4,4,5,5-tetramethyl-2-{4-[2-(3,4,5-trimethoxyphenyl)-vinyl]-phenyl}-[1,3,2]dioxaborolane (1169942-95-3)

Guidance literature:

With sodium t-butanolate; at 20 ℃; for 4h;

DOI:10.1016/j.tetlet.2009.04.003

Reference yield:

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-3-yl-phenyl)-methyl triphenylphosphonium bromide (1169942-85-1) + 3,4,5-trimethoxy-benzaldehyde (86-81-7) → 4,4,5,5-tetramethyl-2-{4-[2-(3,4,5-trimethoxyphenyl)-vinyl]-phenyl}-[1,3,2]dioxaborolane (1169942-95-3)

Guidance literature:

With potassium tert-butylate; In ethyl bromide; at 20 ℃; for 2h;

DOI:10.1016/j.bmcl.2011.05.124

Reference yield:

4-bromomethylphenylboronic acid pinacol ester (138500-85-3) → 4,4,5,5-tetramethyl-2-{4-[2-(3,4,5-trimethoxyphenyl)-vinyl]-phenyl}-[1,3,2]dioxaborolane (1169942-95-3)

Guidance literature:

Multi-step reaction with 2 steps

1: triphenylphosphine hydrobromide / acetonitrile / 6 h / 90 °C

2: potassium tert-butylate / ethyl bromide / 2 h / 20 °C

With potassium tert-butylate; triphenylphosphine hydrobromide; In ethyl bromide; acetonitrile; 2: Wittig reaction;

DOI:10.1016/j.bmcl.2011.05.124

upstream raw materials:

triphenyl-(3,4,5-trimethoxybenzyl)phosphonium bromide

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-3-yl-phenyl)-methyl triphenylphosphonium bromide

3,4,5-trimethoxy-benzaldehyde