4-(4-Tetrahydropyranyl)phenylboronic Acid Pinacol Ester

Base Information

• Chemical Name: 4-(4-Tetrahydropyranyl)phenylboronic Acid Pinacol Ester
• CAS No.: 1312479-26-7
• Molecular Formula: C17H27BO4
• Molecular Weight: 288.195
• Mol file: 1312479-26-7.mol

Synonyms:4-(4-Tetrahydropyranyl)phenylboronic Acid Pinacol Ester;4,4,5,5-tetramethyl-2-(4-(tetrahydro-2H-pyran-4-yl)phenyl)-1,3,2-dioxaborolane

Chemical Property of 4-(4-Tetrahydropyranyl)phenylboronic Acid Pinacol Ester

Chemical Property:

• PSA: 27.69000
• LogP: 2.87980
• Storage Temp.: Inert atmosphere,Room Temperature

Purity/Quality:

97% ^*data from raw suppliers

4-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]tetrahydro-2H-pyran ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 4-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]tetrahydro-2H-pyran, is a building block.

Technology Process of 4-(4-Tetrahydropyranyl)phenylboronic Acid Pinacol Ester

There total 6 articles about 4-(4-Tetrahydropyranyl)phenylboronic 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: 90.0%

1,3-dioxoisoindolin-2-yl tetrahydro-2H-pyran-4-carboxylate + 2-(4-iodophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (73852-88-7) → 4,4,5,5-tetramethyl-2-(4-(tetrahydro-2H-pyran-4-yl)phenyl)-1,3,2-dioxaborolane (1312479-26-7)

Guidance literature:

With chloro-trimethyl-silane; (1,2-dimethoxyethane)dichloronickel(II); pyridine-2-carboxamidine hydrochloride; 1-Bromo-2-chloroethane; zinc; In tetrahydrofuran; N,N-dimethyl acetamide; at 30 ℃; chemoselective reaction; Inert atmosphere; Flow reactor;

DOI:10.1002/chem.201905048

Reference yield: 49.0%

4-(4-bromophenyl)-tetrahydro-2H-pyran (811828-76-9) + bis(pinacol)diborane (73183-34-3) → 4,4,5,5-tetramethyl-2-(4-(tetrahydro-2H-pyran-4-yl)phenyl)-1,3,2-dioxaborolane (1312479-26-7)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; at 80 ℃; Microwave irradiation;

DOI:10.1021/jm501436m

Reference yield:

1.4-dibromobenzene (106-37-6) → 4,4,5,5-tetramethyl-2-(4-(tetrahydro-2H-pyran-4-yl)phenyl)-1,3,2-dioxaborolane (1312479-26-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-butyllithium / tetrahydrofuran / 0.25 h / -78 °C

1.2: 2 h / -78 °C

2.1: triethylsilane; trifluoroacetic acid / dichloromethane / 2.25 h / 0 - 20 °C

3.1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 80 °C / Microwave irradiation

With triethylsilane; n-butyllithium; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm501436m

upstream raw materials:

4-(4-bromophenyl)-tetrahydro-2H-pyran

bis(pinacol)diborane

4-(tetrahydro-2H-pyran-4-yl)benzenamine

2-(4-iodophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Downstream raw materials:

(R)-4-methyl-4-(4-(tetrahydro-2H-pyran-4-yl)phenyl)-1,2,3-oxathiazolidine 2,2-dioxide

(2R)-N-hydroxy-2-methyl-2-(methylsulfonyl)-4-{2-oxo-4-[4-(tetrahydro-2H-pyran-4-yl)phenyl]pyridin-1(2H)-yl}butanamide

(2R)-2-methyl-2-(methylsulfonyl)-4-{2-oxo-4-[4-(tetrahydro-2H-pyran-4-yl)phenyl]pyridin-1(2H)-yl}-N-(tetrahydro-2H-pyran-2-yloxy)butanamide