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

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

CAS No. 243145-83-7
Cat. No. CS-W019272
Purity≥95%
MDL No.MFCD10698519

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2-(4-Fluorobenzyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-W019272

Structure of 243145-83-7

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General Information

CAS No. 243145-83-7
Cat. No. CS-W019272
Purity ≥95%
MDL No. MFCD10698519
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₁₈BFO₂
Molecular Weight 236.09
Synonym(s) 4-Fluorobenzylboronic acid pinacol ester
SMILES CC1(C)OB(CC2=CC=C(F)C=C2)OC1(C)C

Description

This boronate reagent features a 4-fluorobenzyl group integrated into a stable, tetramethyl-substituted dioxaborolane scaffold. The electron-withdrawing fluorine enhances electrophilicity at the aromatic ring, facilitating efficient cross-coupling reactions. Bench-stable and moisture-tolerant, it streamlines the incorporation of fluorinated aryl motifs in synthetic sequences.

Application

2-(4-Fluorobenzyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane serves as a stable, bench-ready boron building block for Suzuki-Miyaura cross-coupling reactions. Its tetramethyl-substituted dioxaborolane moiety enhances air and moisture stability while enabling efficient coupling with aryl halides and triflates. The 4-fluorobenzyl group provides a readily functionalizable handle for downstream derivatization in medicinal chemistry and materials synthesis.

Synthesis

Route1
- 459-46-1
- In-stock
  
  73183-34-3
- ~80%
- In-stock
  
  243145-83-7
References
- Giroux, Andre Tetrahedron Letters, 2003 , vol. 44, # 2 p. 233 - 235
Route2
- 460-00-4
- In-stock
  
  78782-17-9
- ~83%
- In-stock
  
  243145-83-7
References
- Endo, Kohei; Ohkubo, Takahiro; Shibata, Takanori Organic Letters, 2011 , vol. 13, # 13 p. 3368 - 3371
Route3
- 17151-47-2
- In-stock
  
  166330-03-6
- ~73%
- In-stock
  
  243145-83-7
References
- Falck; Bondlela, Muralidhar; Ye, Jianhua; Su-Dong, Cho Tetrahedron Letters, 1999 , vol. 40, # 31 p. 5647 - 5650

Safety Information

Download SDS

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 2.9996
H_Acceptors 2
H_Donors 0
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

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

CAS No. 243145-83-7

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