trans-2-Phenylvinylboronic acid MIDA ester

Base Information

• Chemical Name: trans-2-Phenylvinylboronic acid MIDA ester
• CAS No.: 1152427-93-4
• Molecular Formula: C₁₃H₁₄BNO₄
• Molecular Weight: 259.069
• Mol file: 1152427-93-4.mol

Synonyms:

Chemical Property of trans-2-Phenylvinylboronic acid MIDA ester

Chemical Property:

• Melting Point: 185-195?°C

Purity/Quality:

98%,99%, ^*data from raw suppliers

trans-2-Phenylvinylboronic acid MIDA ester 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: trans-2-Phenylvinylboronic acid MIDA ester is a stable boronic acid surrogate, which can be used as a reactant in Suzuki-Miyaura cross-coupling reactions . It is also used as a precursor to prepare α-borylated phenyl ketone via the Wacker-type oxidation method.

Technology Process of trans-2-Phenylvinylboronic acid MIDA ester

There total 3 articles about trans-2-Phenylvinylboronic acid MIDA ester 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:

N-methyliminodiacetic acid (4408-64-4) + Dihydroxy-styryl-boran (4363-35-3,6783-05-7,60806-02-2) → C13H14BNO4 (1152427-93-4,1313054-20-4)

Guidance literature:

In dimethyl sulfoxide; at 80 ℃;

DOI:10.1002/anie.201611006

Reference yield:

phenylacetylene (536-74-3) → C13H14BNO4 (1152427-93-4,1313054-20-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 24 h / 65 °C

2: N,N-dimethyl-formamide / 24 h / 80 °C

In N,N-dimethyl-formamide;

DOI:10.1021/acs.orglett.5b02861

Reference yield:

PhCHCHBCat (96794-40-0) + N-methyliminodiacetic acid (4408-64-4) → C13H14BNO4 (1152427-93-4,1313054-20-4)

Guidance literature:

In N,N-dimethyl-formamide; at 80 ℃; for 24h;

DOI:10.1021/acs.orglett.5b02861

upstream raw materials:

PhCHCHBCat

N-methyliminodiacetic acid

phenylacetylene

Dihydroxy-styryl-boran

Downstream raw materials:

N-methyliminodiacetyl (2-oxo-1-phenylethyl)boronate

C₁₃H₁₆BNO₅

C₁₃H₁₄BNO₅

MIDA (1,2-dioxo-2-phenylethyl)boronate

Refernces

• 1、 Lee, C. Frank,Holownia, Aleksandra,Bennett, James M.,Elkins, Jonathan M.,St. Denis, Jeffrey D.,Adachi, Shinya,Yudin, Andrei K.. "Oxalyl Boronates Enable Modular Synthesis of Bioactive Imidazoles". . p. 6264 - 6267. Retrieved 2017/05/19.