Vinylboronic acid MIDA ester

Base Information

• Chemical Name: Vinylboronic acid MIDA ester
• CAS No.: 1104636-73-8
• Molecular Formula: C7H10BNO4
• Molecular Weight: 182.972
• Hs Code.: 2934999090
• Mol file: 1104636-73-8.mol

Synonyms:Vinylboronic acid MIDA ester;Vinylboronic acid MIDA ester 97%;6-Methyl-2-vinyl-1,3,6,2-dioxazaborocane-4,8-dione;2-Ethenyl-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione

Chemical Property of Vinylboronic acid MIDA ester

Chemical Property:

• Melting Point: 152-156°C
• PSA: 55.84000
• LogP: -0.83050
• Storage Temp.: 2-8°C

Purity/Quality:

98% ^*data from raw suppliers

6-Methyl-2-vinyl-1,3,6,2-dioxazaborocane-4,8-dione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: MIDA boronates as stable boronic acid surrogates for classically challenging cross-couplingsSuzuki Cross-Coupling with MIDA Boronates

Technology Process of Vinylboronic acid MIDA ester

There total 3 articles about Vinylboronic 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: 71.0%

[Ru((C2H5)2NCS2)(P(C6H5)3)2(CO)H] (56800-89-6) + MeCCB(N-methyliminodiacetato) (1104637-55-9) → 6-methyl-2-vinyl-1,3,6,2-dioxazaborocane-4,8-dione (1104636-73-8) + C49H47BN2O5P2RuS2

Guidance literature:

In dichloromethane; for 36h; Inert atmosphere; Reflux;

DOI:10.1039/c4dt03695f

Reference yield: 23.0%

{RuH(S2CN(CH3)2)(CO)(P(C6H5)3)2} (56800-88-5) + MeCCB(N-methyliminodiacetato) (1104637-55-9) → 6-methyl-2-vinyl-1,3,6,2-dioxazaborocane-4,8-dione (1104636-73-8) + C47H43BN2O5P2RuS2

Guidance literature:

{RuH(S₂CN(CH₃)2)(CO)(P(C₆H₅)3)2}; MeCCB(N-methyliminodiacetato); In dichloromethane; Inert atmosphere; Reflux;

MeCCB(N-methyliminodiacetato); In tetrahydrofuran; for 16h; Inert atmosphere; Reflux;

DOI:10.1039/c4dt03695f

Reference yield:

vinylboronic acid (4363-34-2) + N-methyliminodiacetic acid (4408-64-4) → 6-methyl-2-vinyl-1,3,6,2-dioxazaborocane-4,8-dione (1104636-73-8)

Guidance literature:

In dimethyl sulfoxide; at 80 ℃;

DOI:10.1021/acs.orglett.8b02234

upstream raw materials:

[Ru((C₂H₅)2NCS₂)(P(C₆H₅)3)2(CO)H]

MeCCB(N-methyliminodiacetato)

{RuH(S₂CN(CH₃)2)(CO)(P(C₆H₅)3)2}

vinylboronic acid

Downstream raw materials:

4-(p-fluorophenyl)-3-cyclohexen-1-ol

Refernces

• 1、 Corless, Victoria B.,Holownia, Aleksandra,Foy, Hayden,Mendoza-Sanchez, Rodrigo,Adachi, Shinya,Dudding, Travis,Yudin, Andrei K.. "Synthesis of α-Borylated Ketones by Regioselective Wacker Oxidation of Alkenylboronates". supporting information. p. 5300 - 5303. Retrieved 2018/09/12.