1,3-Bis(trifluoromethyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene

Name: 1,3-Bis(trifluoromethyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene
Brand: ChemScene
Availability: InStock
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CAS No. 69807-91-6
Cat. No. CS-B1243
Purity≥98%
MDL No.MFCD12405516

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1,3-Bis(trifluoromethyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene|CS-B1243

Structure of 69807-91-6

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General Information

CAS No. 69807-91-6
Cat. No. CS-B1243
Purity ≥98%
MDL No. MFCD12405516
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₄H₁₅BF₆O₂
Molecular Weight 340.07
Synonym(s) Pinacol 3,5-di(trifluoromethyl)benzeneboronate; 3,5-Bis(trifluoromethyl)phenylboronic Acid Pinacol Ester
SMILES CC1(C)C(C)(C)OB(C2=CC(C(F)(F)F)=CC(C(F)(F)F)=C2)O1

Description

This boronate-functionalized benzene derivative integrates a trifluoromethyl-rich aromatic core with a stable, moisture-tolerant dioxaborolane handle. The para-substituted boronate moiety enables efficient Suzuki-Miyaura cross-coupling under standard conditions, while the electron-deficient framework enhances reactivity in transition-metal-catalyzed transformations.

Application

1,3-Bis(trifluoromethyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene serves as a versatile boronate building block for Suzuki-Miyaura cross-coupling reactions. The tetramethylboronate moiety enables efficient coupling with aryl halides under mild conditions, while the electron-withdrawing trifluoromethyl groups enhance stability and modulate reactivity. Its bench-stable solid form facilitates handling and purification, making it well-suited for constructing complex aromatic scaffolds in medicinal chemistry and materials science applications.

Synthesis

Route1
- 402-31-3
- In-stock
  
  73183-34-3
- ~87%
- In-stock
  
  69807-91-6
References
- Tagata, Tsuyoshi; Nishida, Mayumi; Nishida, Atsushi Advanced Synthesis and Catalysis, 2010 , vol. 352, # 10 p. 1662 - 1666
Route2
- 402-31-3
- 25015-63-8
- ~88%
- In-stock
  
  69807-91-6
References
- Tse; Cho; Smith 3rd. Organic letters, 2001 , vol. 3, # 18 p. 2831 - 2833
Route3
- In-stock
  
  76-09-5
- 73852-85-4
- ~%
- In-stock
  
  69807-91-6
References
- Takagi, Jun; Yamakawa, Tetsu Tetrahedron Letters, 2013 , vol. 54, # 2 p. 166 - 169

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 4.0234
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

Chemical Synthesis Organometallic Reagents Organoboron Boronic Acids and Derivatives

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1,3-Bis(trifluoromethyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene

CAS No. 69807-91-6

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