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

Name: 2-(2,4-Difluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Brand: ChemScene
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CAS No. 288101-48-4
Cat. No. CS-0153877
Purity≥98%
MDL No.MFCD05663880

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2-(2,4-Difluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0153877

Structure of 288101-48-4

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General Information

CAS No. 288101-48-4
Cat. No. CS-0153877
Purity ≥98%
MDL No. MFCD05663880
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₁₅BF₂O₂
Molecular Weight 240.05
Synonym(s) 2,4-DIFLUOROPHENYLBORONIC ACID, PINACOL ESTER
SMILES CC1(C)C(C)(C)OB(C2=C(C=C(C=C2)F)F)O1

Description

This boronate ester features a 2,4-difluorophenyl moiety paired with a tetramethyl-substituted dioxaborolane ring, delivering enhanced stability and compatibility in Suzuki-Miyaura coupling reactions. The electron-withdrawing fluorine substituents improve reactivity while maintaining bench-stable handling characteristics under standard conditions.

Application

2-(2,4-Difluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane serves as a stable, bench-ready boronate building block for Suzuki-Miyaura cross-coupling reactions. Its tetramethyl-substituted dioxaborolane ring enhances air and moisture stability while maintaining high reactivity with aryl halides and pseudohalides. The 2,4-difluorophenyl moiety provides orthogonal functionalization potential and is commonly found in bioactive heterocycles, enabling efficient construction of complex pharmaceutical scaffolds under mild conditions.

Synthesis

Route1
- In-stock
  
  348-57-2
- In-stock
  
  73183-34-3
- ~68%
- In-stock
  
  288101-48-4
References
- Chotana, Ghayoor A.; Rak, Michael A.; Smith, Milton R. Journal of the American Chemical Society, 2005 , vol. 127, # 30 p. 10539 - 10544

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 : H315-H319-H335
Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 18.46
LogP 2.264
H_Acceptors 2
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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

CAS No. 288101-48-4

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