Bromotriphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)phosphorane

Base Information

• Chemical Name: Bromotriphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)phosphorane
• CAS No.: 1169942-85-1
• Molecular Formula: C31H33BBrO2P
• Molecular Weight: 559.291
• Hs Code.: 2931900090
• Mol file: 1169942-85-1.mol

Synonyms:Bromotriphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)phosphorane

Chemical Property of Bromotriphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)phosphorane

Chemical Property:

• Melting Point: 265-270°C
• PSA: 32.05000
• LogP: 6.32550

Purity/Quality:

97% ^*data from raw suppliers

Bromotriphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)phosphorane ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Bromotriphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)phosphorane (CAS# 1169942-85-1) is a lipogenic inhibitor for use in dyslipidemias and cancer. As a building block, bromotriphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)phosphorane can be fluorinated for use of imaging with positron emission tomography.

Technology Process of Bromotriphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)phosphorane

There total 5 articles about Bromotriphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)phosphorane 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: 97.0%

triphenylphosphine (603-35-0) + 4-bromomethylphenylboronic acid pinacol ester (138500-85-3) → 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-3-yl-phenyl)-methyl triphenylphosphonium bromide (1169942-85-1)

Guidance literature:

In acetonitrile; at 85 ℃; for 12h;

DOI:10.1007/s00775-010-0690-6

Reference yield: 92.0%

4-bromomethylphenylboronic acid pinacol ester (138500-85-3) → 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-3-yl-phenyl)-methyl triphenylphosphonium bromide (1169942-85-1)

Guidance literature:

With triphenylphosphine hydrobromide; In acetonitrile; at 90 ℃; for 6h;

DOI:10.1016/j.bmcl.2011.05.124

Reference yield:

4-tolyl iodide (624-31-7) → 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-3-yl-phenyl)-methyl triphenylphosphonium bromide (1169942-85-1)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / dimethyl sulfoxide / 80 °C / Inert atmosphere

2: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / acetonitrile / 2 h / 90 °C

3: acetonitrile / 12 h / 90 °C

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); potassium acetate; In dimethyl sulfoxide; acetonitrile;

upstream raw materials:

triphenylphosphine

4-bromomethylphenylboronic acid pinacol ester

4-tolyl iodide

bis(pinacol)diborane

Downstream raw materials:

4-{2-[4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-phenyl]-vinyl}-pyridine

(Z)-3,5-di-tert-butyl-2-hydroxy-4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)stilbene

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

(E)-4-(boronic acid)-4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)stilbene

Refernces

Design, synthesis and biological study of pinacolyl boronate-substituted stilbenes as novel lipogenic inhibitors

10.1016/j.bmcl.2011.05.124

This study investigated the creation and evaluation of a series of pinacolyl borate-substituted stilbenes as potential inhibitors of lipogenesis. The researchers synthesized a test library of these compounds, which are derivatives of 4,4,5,5-tetramethyl-2-(4-substituted styrylphenyl)-1,3,2-dioxaborolane. The key chemical involved in the synthesis was 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolatophenyl)-methyltriphenylphosphine bromide (3), which reacted with various aldehydes in the presence of tBuONa in DMF to generate boron-containing stilbenes derivatives. Among these derivatives, BF102 and BF175 were shown to effectively inhibit lipogenesis by inhibiting the expression of lipogenic genes in hepatocytes. BF102 also inhibited cholesterol biosynthesis by reducing the expression of the HMG-CoA reductase gene. The study suggests that BF102 may be a promising lead for the development of the next generation of lipid-lowering drugs, with preliminary in vivo data showing no significant toxicity in mice at high doses.

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