1-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethan-1-one

Name: 1-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethan-1-one
Brand: ChemScene
Availability: InStock
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CAS No. 214360-49-3
Cat. No. CS-0094692
Purity≥95%
MDL No.MFCD05863923

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1-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethan-1-one|CS-0094692

Structure of 214360-49-3

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General Information

CAS No. 214360-49-3
Cat. No. CS-0094692
Purity ≥95%
MDL No. MFCD05863923
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₄H₁₉BO₃
Molecular Weight 246.11
Synonym(s) 1-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethanone
SMILES CC(C1=CC=CC(B2OC(C)(C)C(C)(C)O2)=C1)=O

Description

1-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethan-1-one features a boronate ester group flanked by an electron-rich aryl ring and a ketone-bearing side chain. This structure enables reliable cross-coupling in palladium-catalyzed reactions under standard conditions. The tetramethyl-substituted dioxaborolane moiety enhances stability and resistance to hydrolysis during handling. Designed for efficient integration into complex molecular architectures, this reagent streamlines the synthesis of biaryl ketones in medicinal chemistry and materials science applications.

Application

1-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethan-1-one serves as a versatile boron-containing building block for Suzuki-Miyaura cross-coupling reactions. The sterically hindered tetramethyl-substituted dioxaborolane moiety enhances stability and minimizes protodeboronation, enabling reliable coupling with aryl halides under mild conditions. Its ketone functionality provides orthogonal reactivity, facilitating downstream transformations such as reductions or nucleophilic additions. Ideal for constructing biaryl scaffolds in medicinal chemistry and materials science applications.

Synthesis

Route1
- 138313-22-1
- 25015-63-8
- ~53%
- In-stock
  
  214360-49-3
References
- Journal of Organic Chemistry, , vol. 65, # 1 p. 164 - 168
Route2
- 99-02-5
- In-stock
  
  73183-34-3
- ~79%
- In-stock
  
  214360-49-3
References
- Organic Letters, , vol. 13, # 6 p. 1366 - 1369
Route3
- In-stock
  
  2142-63-4
- In-stock
  
  73183-34-3
- ~94%
- In-stock
  
  214360-49-3
References
- Advanced Synthesis and Catalysis, , vol. 352, # 11-12 p. 2002 - 2010

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 : P260-P261-P264-P271-P280-P302+P352-P304+P340-P362-P405-P501

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Computational Chemistry Data

TPSA 35.53
LogP 2.1884
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Ketone

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

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1-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethan-1-one

CAS No. 214360-49-3

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