4,4,5,5-Tetramethyl-2-(p-tolyl)-1,3,2-dioxaborolane

Name: 4,4,5,5-Tetramethyl-2-(p-tolyl)-1,3,2-dioxaborolane
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 195062-57-8
Cat. No. CS-W022040
Molecule weight218.10
Purity≥98%
MDL No.MFCD03453662

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4,4,5,5-Tetramethyl-2-(p-tolyl)-1,3,2-dioxaborolane|CS-W022040

Structure of 195062-57-8

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General Information

CAS No. 195062-57-8
Cat. No. CS-W022040
Purity ≥98%
MDL No. MFCD03453662
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₁₉BO₂
Molecular Weight 218.10
Synonym(s) p-Tolylboronic Acid Pinacol Ester
SMILES CC1=CC=C(B2OC(C)(C)C(C)(C)O2)C=C1

Description

This boronate ester features a sterically protected tetramethylcyclopentadienone core paired with a para-tolyl group, delivering enhanced stability and reactivity in Suzuki-Miyaura cross-coupling reactions. The robust boronate moiety enables efficient coupling under mild conditions, while the p-tolyl substituent improves solubility and handling.

Application

4,4,5,5-Tetramethyl-2-(p-tolyl)-1,3,2-dioxaborolane serves as a stable, bench-ready boron reagent for Suzuki-Miyaura cross-coupling reactions. Its sterically hindered dioxaborolane ring enhances air and moisture tolerance, enabling reliable coupling with aryl and heteroaryl halides under standard conditions. The p-tolyl group provides a robust handle for sequential functionalization, making it ideal for constructing biaryl scaffolds in medicinal chemistry and materials synthesis.

Synthesis

Route1
- 106-38-7
- In-stock
  
  185990-03-8
- ~66%
- In-stock
  
  195062-57-8
References
- Yamamoto, Eiji; Izumi, Kiyotaka; Horita, Yuko; Ito, Hajime Journal of the American Chemical Society, 2012 , vol. 134, # 49 p. 19997 - 20000
Route2
- 106-43-4
- In-stock
  
  73183-34-3
- ~70%
- 106-42-3
- In-stock
  
  195062-57-8
References
- Kawamorita, Soichiro; Ohmiya, Hirohisa; Iwai, Tomohiro; Sawamura, Masaya Angewandte Chemie - International Edition, 2011 , vol. 50, # 36 p. 8363 - 8366
Route3
- 108-88-3
- 25015-63-8
- ~%
- In-stock
  
  195062-57-8
- In-stock
  
  195062-59-0
- In-stock
  
  253342-48-2
References
- Angewandte Chemie - International Edition, , vol. 40, # 11 p. 2168 - 2171

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

Quality Control

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Computational Chemistry Data

TPSA 18.46
LogP 2.29422
H_Acceptors 2
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Material Science Material Composite Block Liquid Crystal (LC) Block

Material Science Material Building Blocks Liquid Crystal (LC) Building Blocks Benzeneboronic Acids

Chemical Synthesis Organometallic Reagents Organoboron Boronic Acids and Derivatives

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4,4,5,5-Tetramethyl-2-(p-tolyl)-1,3,2-dioxaborolane

CAS No. 195062-57-8

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