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

Name: 2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 68716-49-4
Cat. No. CS-0036048
Purity≥97%
MDL No.MFCD11110553

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2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0036048

Structure of 68716-49-4

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General Information

CAS No. 68716-49-4
Cat. No. CS-0036048
Purity ≥97%
MDL No. MFCD11110553
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₁₆BBrO₂
Molecular Weight 282.97
Synonym(s) 4-Bromophenylboronic Acid Pinacol Ester
SMILES CC1(C)C(C)(C)OB(C2=CC=C(C=C2)Br)O1

Description

2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is a bench-stable boronate reagent featuring a para-brominated aryl group. This electrophilically active moiety integrates seamlessly into Suzuki-Miyaura cross-coupling reactions, enabling efficient C–C bond formation under standard conditions. The sterically shielded dioxaborolane core enhances stability and minimizes protodeboronation.

Application

2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane serves as a stable, bench-ready boron reagent for palladium-catalyzed cross-coupling reactions. Its aryl bromide functionality enables efficient Suzuki-Miyaura coupling with a wide range of boronic acids and halides, offering high functional group tolerance and predictable regiochemistry. The tetramethyl-substituted dioxaborolane ring enhances air and moisture stability, simplifying handling and purification in routine synthetic workflows.

Synthesis

Route1
- In-stock
  
  589-87-7
- 25015-63-8
- ~95%
- In-stock
  
  68716-49-4
References
- Melaimi, Mohand; Mathey, Francois; Le Floch, Pascal Journal of Organometallic Chemistry, 2001 , vol. 640, # 1-2 p. 197 - 199
Route2
- In-stock
  
  76-09-5
- In-stock
  
  5467-74-3
- ~99%
- In-stock
  
  68716-49-4
References
- MICROBIA, INC. Patent: WO2006/122117 A2, 2006 ; Location in patent: Page/Page column 23 ;
Route3
- In-stock
  
  673-40-5
- In-stock
  
  73183-34-3
- ~94%
- In-stock
  
  68716-49-4
References
- Ma, Yudao; Song, Chun; Jiang, Wei; Xue, Guoping; Cannon, John F.; Wang, Xiaomei; Andrus, Merritt B. Organic Letters, 2003 , vol. 5, # 24 p. 4635 - 4638

Safety Information

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GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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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

Key Words

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

CAS No. 68716-49-4

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