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

Base Information

• Chemical Name: 2-(4-Methoxybenzyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 475250-52-3
• Molecular Formula: C14H21BO3
• Molecular Weight: 248.13
• European Community (EC) Number: 677-589-1
• DSSTox Substance ID: DTXSID20475812
• Nikkaji Number: J1.147.025D
• Wikidata: Q72489252
• Mol file: 475250-52-3.mol

Synonyms:475250-52-3;2-(4-Methoxybenzyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;4-Methoxybenzylboronic Acid Pinacol Ester;2-[(4-methoxyphenyl)methyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;MFCD10698526;1,3,2-Dioxaborolane, 2-[(4-methoxyphenyl)methyl]-4,4,5,5-tetramethyl-;DTXSID20475812;HPNLRRQVSZVKHY-UHFFFAOYSA-N;AKOS015852237;AB62302;AS-10435;SY013338;A7278;CS-0153821;FT-0649841;M2071;T72506;3-hydroxy-2,3-dimethylbutan-2-yl hydrogen 4-methoxybenzylboronate;4-methoxy-1-[(4,4,5,5-tetramethyl(1,3,2-dioxaborolan-2-yl))methyl]benzene

Chemical Property of 2-(4-Methoxybenzyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property:

• Refractive Index: 1.497
• Boiling Point: 311.191 °C at 760 mmHg
• Flash Point: 142.003 °C
• PSA: 27.69000
• Density: 1.018 g/cm³
• LogP: 3.13550
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 248.1583747
• Heavy Atom Count: 18
• Complexity: 267

Purity/Quality:

97% ^*data from raw suppliers

2-(4-Methoxybenzyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)CC2=CC=C(C=C2)OC

Technology Process of 2-(4-Methoxybenzyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

There total 31 articles about 2-(4-Methoxybenzyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 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: 98.0%

1-bromo-4-methoxy-benzene (104-92-7) + 4,4,5,5-tetramethyl-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-1,3,2-dioxaborolane (78782-17-9) → 2-[(4-methoxyphenyl)methyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (475250-52-3)

Guidance literature:

With bis(tri-t-butylphosphine)palladium⁽⁰⁾; potassium hydroxide; In 1,4-dioxane; water; at 20 ℃; for 2h; Time; chemoselective reaction;

DOI:10.1246/cl.130643

Reference yield: 93.0%

p-methoxybenzyl chloride (824-94-2) + bis(pinacol)diborane (73183-34-3) → 2-[(4-methoxyphenyl)methyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (475250-52-3)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In 1,4-dioxane; at 100 ℃; for 18h;

DOI:10.1016/S0040-4039(02)02566-2

Reference yield: 86.0%

4-Methoxybenzyl alcohol (105-13-5) + bis(pinacol)diborane (73183-34-3) → 2-[(4-methoxyphenyl)methyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (475250-52-3)

Guidance literature:

With gold-nanoparticles supported on TiO₂; In 1,4-dioxane; at 60 ℃; for 1h;

DOI:10.1021/acscatal.0c03771

upstream raw materials:

(p-methoxyphenyl)tri-n-butylstannane

pinacol (bromomethyl)boronate

p-methoxybenzyl chloride

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

Downstream raw materials:

4-methoxy-N-methyl-N-phenylbenzenemethanamine

p-ethylanisole

1-(4-methoxyphenyl)but-3-en-2-ol

5-(4-methoxyphenyl)pentan-2-one