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

Name: 2-(2-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Brand: ChemScene
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CAS No. 269410-06-2
Cat. No. CS-0173865
Purity≥98%
MDL No.None

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2-(2-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0173865

Structure of 269410-06-2

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General Information

CAS No. 269410-06-2
Cat. No. CS-0173865
Purity ≥98%
MDL No. None
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₁₆BBrO₂
Molecular Weight 282.97
Synonym(s) 2-Bromophenylboronic Acid Pinacol Ester
SMILES CC1(C(C)(OB(O1)C2=CC=CC=C2Br)C)C

Description

This boronate moiety integrates a brominated aryl group within a stable, sterically shielded dioxaborolane framework. Designed for efficient cross-coupling reactions, it enables direct functionalization of complex heterocycles under standard conditions. The para-bromophenyl substitution enhances reactivity in palladium-catalyzed transformations while maintaining bench-stability and moisture tolerance.

Application

2-(2-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane serves as a stable, bench-ready boron building block for palladium-catalyzed cross-coupling reactions. Its aryl bromide functionality enables efficient Suzuki-Miyaura coupling with diverse boronic acids and electrophiles, facilitating the construction of biaryl scaffolds. The tetramethyl-substituted dioxaborolane ring enhances shelf stability and minimizes protodeboronation, while the ortho-bromine substitution allows for selective functionalization in complex molecule synthesis.

Synthesis

Route1
- In-stock
  
  76-09-5
- 22092-92-8
- 10448-07-4
- ~71%
- In-stock
  
  269410-06-2
References
- WO2014/9169 A1, ; Page/Page column 63 ;
Route2
- In-stock
  
  583-55-1
- 25015-63-8
- ~%
- In-stock
  
  269410-07-3
- In-stock
  
  269410-06-2
References
- US6680401 B1, ; Page column 57 ;
Route3
- In-stock
  
  76-09-5
- In-stock
  
  244205-40-1
- ~86%
- In-stock
  
  269410-06-2
References
- Journal of the American Chemical Society, , vol. 124, # 28 p. 8348 - 8360

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-H335
Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P362-P405-P501

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Computational Chemistry Data

TPSA 18.46
LogP 2.7483
H_Acceptors 2
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Chemical Synthesis Organometallic Reagents Organoboron Boronic Acids and Derivatives

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

CAS No. 269410-06-2

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