Acetyleneboronic acid MIDA ester, Acetynylboronic acid MIDA ester, Ethyneboronic acid MIDA ester

Base Information

• Chemical Name: Acetyleneboronic acid MIDA ester, Acetynylboronic acid MIDA ester, Ethyneboronic acid MIDA ester
• CAS No.: 1104637-53-7
• Molecular Formula: C7H8BNO4
• Molecular Weight: 180.956
• Mol file: 1104637-53-7.mol

Synonyms:Acetyleneboronic acid MIDA ester, Acetynylboronic acid MIDA ester, Ethyneboronic acid MIDA ester;Ethynylboronic acid MIDA ester;Acetyleneboronic acid MIDA ester;Acetynylboronic acid MIDA ester;Ethyneboronic acid MIDA ester

Chemical Property of Acetyleneboronic acid MIDA ester, Acetynylboronic acid MIDA ester, Ethyneboronic acid MIDA ester

Chemical Property:

• Melting Point: 208-209 °C
• PSA: 55.84000
• LogP: -1.38330
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

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

Ethynylboronic acid MIDA ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Suzuki Cross-Coupling with MIDA Boronates

Technology Process of Acetyleneboronic acid MIDA ester, Acetynylboronic acid MIDA ester, Ethyneboronic acid MIDA ester

There total 4 articles about Acetyleneboronic acid MIDA ester, Acetynylboronic acid MIDA ester, Ethyneboronic 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: 80.0%

ethynyl boronic acid + (N-methylimino)diacetic acid anhydride (13480-36-9) → B-ethynyl N-methyliminodiacetic acid boronate (1104637-53-7)

Guidance literature:

In 1,4-dioxane; at 70 ℃; for 24h; Dean-Stark;

DOI:10.1021/acs.orglett.0c02449

Reference yield: 74.0%

N-methyliminodiacetic acid (4408-64-4) + acetylenemagnesium bromide (4301-14-8) → B-ethynyl N-methyliminodiacetic acid boronate (1104637-53-7)

Guidance literature:

acetylenemagnesium bromide; With Trimethyl borate; In tetrahydrofuran; at -78 - 20 ℃; for 4.08333h; Inert atmosphere;

N-methyliminodiacetic acid; In tetrahydrofuran; hexane; dimethyl sulfoxide; at 120 - 160 ℃; for 1.5h; Inert atmosphere;

DOI:10.1002/anie.201004911

Reference yield: 74.0%

N-methyliminodiacetic acid (4408-64-4) + BrMg(1+)*C5H10BO3(1-) → B-ethynyl N-methyliminodiacetic acid boronate (1104637-53-7)

Guidance literature:

In tetrahydrofuran; hexane; dimethyl sulfoxide; at 120 - 160 ℃; Product distribution / selectivity; Inert atmosphere;

upstream raw materials:

N-methyliminodiacetic acid

acetylenemagnesium bromide

Trimethyl borate

(N-methylimino)diacetic acid anhydride

Downstream raw materials:

C₁₄H₁₄BNO₅

2-methyl-phenylethynylboronic acid MIDA ester

C₁₄H₁₄BNO₅

C₁₄H₁₁BN₂O₄

Refernces

• 1、 Kelly, Aidan M.,Chen, Peng-Jui,Klubnick, Jenna,Blair, Daniel J.,Burke, Martin D.. "A Mild Method for Making MIDA Boronates". supporting information. p. 9408 - 9414. Retrieved 2020/09/15.
• 2、 -. "Methods for Forming Protected Organoboronic Acids". Page/Page column 14. . Retrieved 2011/09/14.