4,4,5,5-Tetramethyl-2-(3-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane

Name: 4,4,5,5-Tetramethyl-2-(3-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane
Brand: ChemScene
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CAS No. 325142-82-3
Cat. No. CS-W000911
Purity≥98%
MDL No.MFCD05863925

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4,4,5,5-Tetramethyl-2-(3-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane|CS-W000911

Structure of 325142-82-3

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General Information

CAS No. 325142-82-3
Cat. No. CS-W000911
Purity ≥98%
MDL No. MFCD05863925
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₁₆BF₃O₂
Molecular Weight 272.07
Synonym(s) 3-(Trifluoromethyl)phenylboronic Acid Pinacol Ester
SMILES CC1(C)OB(OC1(C)C)c1cccc(c1)C(F)(F)F

Description

This boronate ester features a trifluoromethyl-substituted aryl group, enhancing electron deficiency and stability. The tetramethyl substitution ensures high bench stability and resistance to hydrolysis. It integrates readily into Suzuki-Miyaura cross-coupling reactions under mild conditions, delivering efficient coupling with diverse halides and pseudohalides.

Application

4,4,5,5-Tetramethyl-2-(3-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane serves as a stable, bench-ready boron reagent for Suzuki-Miyaura cross-coupling reactions. Its trifluoromethyl-substituted aryl group enables efficient coupling with a range of halides and pseudohalides, offering enhanced electron-withdrawing character for improved reactivity. The tetramethyl substituents provide excellent air and moisture stability, facilitating handling and purification, while the dioxaborolane core ensures compatibility with standard catalytic conditions.

Synthesis

Route1
- 98-16-8
- In-stock
  
  73183-34-3
- ~80%
- In-stock
  
  325142-82-3
References
- Mo, Fanyang; Jiang, Yubo; Qiu, Di; Zhang, Yan; Wang, Jianbo Angewandte Chemie - International Edition, 2010 , vol. 49, # 10 p. 1846 - 1849
Route2
- In-stock
  
  401-78-5
- 61676-62-8
- ~86%
- In-stock
  
  325142-82-3
References
- Chi, Yun; Hsu, Chien-Wei; Ho, Shu-Te Patent: US2013/18189 A1, 2013 ; Location in patent: Paragraph 0066; 0067 ;
Route3
- 98-15-7
- In-stock
  
  73183-34-3
- ~65%
- In-stock
  
  325142-82-3
References
- Billingsley, Kelvin L.; Barder, Timothy E.; Buchwald, Stephen L. Angewandte Chemie - International Edition, 2007 , vol. 46, # 28 p. 5359 - 5363

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
Precautionary Statements : P264-P270-P330-P501

Quality Control

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Computational Chemistry Data

TPSA 18.46
LogP 3.0046
H_Acceptors 2
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Fluoride

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Chemical Synthesis Organometallic Reagents Organoboron Boronic Acids and Derivatives

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

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4,4,5,5-Tetramethyl-2-(3-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane

CAS No. 325142-82-3

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