Isopropenylboronic acid MIDA ester

Base Information

• Chemical Name: Isopropenylboronic acid MIDA ester
• CAS No.: 1104637-47-9
• Molecular Formula: C8H12BNO4
• Molecular Weight: 196.999
• Hs Code.: 2934999090
• Mol file: 1104637-47-9.mol

Synonyms:Isopropenylboronic acid MIDA ester;6-Methyl-2-(prop-1-en-2-yl)-1,3,6,2-dioxazaborocane-4,8-dione

Chemical Property of Isopropenylboronic acid MIDA ester

Chemical Property:

• Melting Point: 136-140℃
• PSA: 55.84000
• LogP: -0.44040
• Storage Temp.: 2-8°C

Purity/Quality:

98%min ^*data from raw suppliers

Isopropenylboronic acid MIDA ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Reactant for:? ;Stereoretentive Suzuki-Miyaura coupling1Suzuki Cross-Coupling with MIDA Boronates

Technology Process of Isopropenylboronic acid MIDA ester

There total 3 articles about Isopropenylboronic 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: 94.0%

N-methyliminodiacetic acid (4408-64-4) + potassium isopropenyltrifluoroborane → isopropene boronic acid MIDA ester (1104637-47-9)

Guidance literature:

With chloro-trimethyl-silane; potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; Inert atmosphere;

DOI:10.1021/acs.joc.5b00182

Reference yield: 81.0%

N-methyliminodiacetic acid (4408-64-4) + BrMg(1+)*C6H14BO3(1-) → isopropene boronic acid MIDA ester (1104637-47-9)

Guidance literature:

In tetrahydrofuran; dimethyl sulfoxide; at 100 - 115 ℃;

Reference yield:

6-methyl-2-(pyridin-2-yl)-1,3,6,2-dioxazaborocane-4,8-dione (1104637-58-2) → isopropene boronic acid MIDA ester (1104637-47-9)

Guidance literature:

Multi-step reaction with 2 steps

1: methanol; water / 16 h / 20 °C

2: potassium carbonate; chloro-trimethyl-silane / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

With chloro-trimethyl-silane; potassium carbonate; In methanol; water; N,N-dimethyl-formamide;

DOI:10.1021/acs.joc.5b00182

upstream raw materials:

N-methyliminodiacetic acid

6-methyl-2-(pyridin-2-yl)-1,3,6,2-dioxazaborocane-4,8-dione

Downstream raw materials:

1-(1-methylethenyl)-2-nitrobenzene

isopropenylboronic acid

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