3,5-Dichloro-4-hydroxyphenylboronic acid pinacol ester

Base Information

• Chemical Name: 3,5-Dichloro-4-hydroxyphenylboronic acid pinacol ester
• CAS No.: 1003298-87-0
• Molecular Formula: C12H17BCl2O4
• Molecular Weight: 288.966
• Hs Code.: 2931900090
• Mol file: 1003298-87-0.mol

Synonyms:3,5-Dichloro-4-hydroxyphenylboronic acid pinacol ester;2,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Chemical Property of 3,5-Dichloro-4-hydroxyphenylboronic acid pinacol ester

Chemical Property:

• Melting Point: 108.0 to 112.0 °C
• Boiling Point: 103°C/0.3mmHg(lit.)
• PKA: 6.72±0.40(Predicted)
• Density: 1.28
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: soluble in Methanol

Purity/Quality:

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

2,6-dichloro-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3,5-Dichloro-4-hydroxyphenylboronic acid pinacol ester

There total 2 articles about 3,5-Dichloro-4-hydroxyphenylboronic acid pinacol 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: 75.0%

4-bromo-2,6-dichloro-phenol (3217-15-0) + bis(pinacol)diborane (73183-34-3) → 2,6-dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (1003298-87-0)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80 ℃; for 24h;

Reference yield:

2,6-dichloroanisole (1984-65-2) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 2,6-dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (1003298-87-0)

Guidance literature:

(Ind)Ir(COD); 1,2-bis(dimethylphosphanyl)ethane; at 150 ℃; for 16h;

Reference yield: 75.0%

2,6-dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (1003298-87-0) + 1-(6-bromo-4-((trans-4-((dimethyl-d6-amino)methyl)cyclohexyl)amino)quinolin-3-yl)ethanone → 1-(6-(3,5-dichloro-4-hydroxyphenyl)-4-((trans-4-((dimethyl-d6-amino)methyl)cyclohexyl)amino)quinolin-3-yl)ethanone dihydrochloride

Guidance literature:

2,6-dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol; 1-(6-bromo-4-((trans-4-((dimethyl-d6-amino)methyl)cyclohexyl)amino)quinolin-3-yl)ethanone; With caesium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; water; at 80 ℃; for 2h; Inert atmosphere;

With hydrogenchloride; In methanol; water;

upstream raw materials:

2,6-dichloroanisole

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

4-bromo-2,6-dichloro-phenol

bis(pinacol)diborane

Downstream raw materials:

(S)-tert-butyl 1-{5-[3-(cyclopropanecarbonyl)-6-(3,5-dichloro-4-hydroxyphenyl)-1,5-naphthyridin-4-ylamino]pyridin-2-yl}piperidin-3-ylcarbamate

Refernces

• 1、 Allegretti, Paul A.,Horton, Timothy M.,Abdolazimi, Yassan,Moeller, Hannah P.,Yeh, Benjamin,Caffet, Matthew,Michel, Guillermina,Smith, Mark,Annes, Justin P.. "Generation of highly potent DYRK1A-dependent inducers of human β-Cell replication via Multi-Dimensional compound optimization". supporting information. . Retrieved 2019/12/09.
• 2、 -. "1,5-NAPHTHYRIDINE DERIVATIVES AND MELK INHIBITORS CONTAINING THE SAME". Page/Page column 156; 157. . Retrieved 2013/07/31.