(E)-2-hydroxy-5-nitro-4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)stilbene

Base Information

• Chemical Name: (E)-2-hydroxy-5-nitro-4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)stilbene
• CAS No.: 1169942-93-1
• Molecular Formula: C₂₀H₂₂BNO₅
• Molecular Weight: 367.209
• Mol file: 1169942-93-1.mol

Synonyms:(E)-2-hydroxy-5-nitro-4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)stilbene

Chemical Property of (E)-2-hydroxy-5-nitro-4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)stilbene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-2-hydroxy-5-nitro-4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)stilbene

There total 4 articles about (E)-2-hydroxy-5-nitro-4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)stilbene 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:

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-3-yl-phenyl)-methyl triphenylphosphonium bromide (1169942-85-1) + 5-Nitrosalicylaldehyde (97-51-8) → (Z)-2-hydroxy-5-nitro-4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)stilbene (1394005-07-2) + (E)-2-hydroxy-5-nitro-4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)stilbene (1169942-93-1)

Guidance literature:

With sodium t-butanolate; In N,N-dimethyl-formamide; at 20 ℃; for 12h; optical yield given as %de; Inert atmosphere;

DOI:10.1016/j.tetlet.2009.04.003

Reference yield:

4-bromomethylphenylboronic acid pinacol ester (138500-85-3) → (Z)-2-hydroxy-5-nitro-4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)stilbene (1394005-07-2) + (E)-2-hydroxy-5-nitro-4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)stilbene (1169942-93-1)

Guidance literature:

Multi-step reaction with 2 steps

1: acetonitrile / 90 °C

2: sodium t-butanolate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

With sodium t-butanolate; In N,N-dimethyl-formamide; acetonitrile; 2: |Wittig Olefination;

DOI:10.1016/j.jorganchem.2015.08.007

Reference yield:

p-tolylboronic pinacol ester (195062-57-8) → (Z)-2-hydroxy-5-nitro-4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)stilbene (1394005-07-2) + (E)-2-hydroxy-5-nitro-4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)stilbene (1169942-93-1)

Guidance literature:

Multi-step reaction with 3 steps

1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 12 h / Reflux

2: acetonitrile / 90 °C

3: sodium t-butanolate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); sodium t-butanolate; In tetrachloromethane; N,N-dimethyl-formamide; acetonitrile; 3: |Wittig Olefination;

DOI:10.1016/j.jorganchem.2015.08.007

upstream raw materials:

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

5-Nitrosalicylaldehyde

4-bromomethylphenylboronic acid pinacol ester

p-tolylboronic pinacol ester