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

Name: 2-(4-Methoxybenzyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Brand: ChemScene
Availability: InStock
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CAS No. 475250-52-3
Cat. No. CS-0153821
Purity≥96%
MDL No.MFCD10698526

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2-(4-Methoxybenzyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0153821

Structure of 475250-52-3

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General Information

CAS No. 475250-52-3
Cat. No. CS-0153821
Purity ≥96%
MDL No. MFCD10698526
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₄H₂₁BO₃
Molecular Weight 248.13
Synonym(s) 4-Methoxybenzylboronic Acid Pinacol Ester
SMILES CC1(C)C(C)(C)OB(CC2=CC=C(C=C2)OC)O1

Description

This boronate ester features a methoxy-substituted benzyl group that enhances solubility and stability in polar solvents. The tetramethyl-1,3,2-dioxaborolane core provides excellent shelf life and reactivity in Suzuki-Miyaura cross-coupling reactions under standard conditions.

Application

2-(4-Methoxybenzyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane serves as a stable, bench-friendly boron building block for Suzuki-Miyaura cross-coupling reactions. The methoxy-substituted benzyl group provides enhanced solubility and functional group tolerance, enabling efficient late-stage diversification in complex molecule synthesis. Its high reactivity and minimal protodeboronation under standard coupling conditions make it ideal for constructing biaryl and heteroaryl scaffolds in medicinal chemistry and materials science applications.

Synthesis

Route1
- 104-92-7
- In-stock
  
  78782-17-9
- ~96%
- In-stock
  
  475250-52-3
References
- Endo, Kohei; Kurosawa, Fumiya; Ukaji, Yutaka Chemistry Letters, 2013 , vol. 42, # 11 p. 1363 - 1365
Route2
- 824-94-2
- In-stock
  
  73183-34-3
- ~92%
- In-stock
  
  475250-52-3
References
- Giroux, Andre Tetrahedron Letters, 2003 , vol. 44, # 2 p. 233 - 235
Route3
- 824-94-2
- 25015-63-8
- ~84%
- In-stock
  
  475250-52-3
References
- Pintaric; Laza; Olivero; Dunach Tetrahedron Letters, 2004 , vol. 45, # 43 p. 8031 - 8033

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H315-H319
Precautionary Statements : P264-P280-P302+P352-P362

Quality Control

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Computational Chemistry Data

TPSA 27.69
LogP 2.8691
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 3

Other Classifications

Building Blocks Skeleton Aliphatic heterocycle compounds Other aliphatic heterocycles compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Chemical Synthesis Organometallic Reagents Organoboron Boronic Acids and Derivatives

Key Words

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

CAS No. 475250-52-3

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