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

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

CAS No. 1073339-21-5
Cat. No. CS-0175669
Purity≥98%
MDL No.None

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4,4,5,5-Tetramethyl-2-(2-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane|CS-0175669

Structure of 1073339-21-5

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General Information

CAS No. 1073339-21-5
Cat. No. CS-0175669
Purity ≥98%
MDL No. None
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₁₆BF₃O₂
Molecular Weight 272.07
Synonym(s) 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(trifluoromethyl)benzene
SMILES CC1(C(C)(OB(O1)C2=CC=CC=C2C(F)(F)F)C)C

Description

This boronate reagent features a trifluoromethyl-substituted aryl group paired with a sterically protected dioxaborolane ring, enabling stable coupling in Suzuki-Miyaura reactions. The electron-deficient phenyl moiety enhances reactivity while the tetramethyl substitution ensures bench-stable handling and resistance to protodeboronation.

Application

4,4,5,5-Tetramethyl-2-(2-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane serves as a stable, bench-ready boron reagent for palladium-catalyzed cross-coupling reactions. It enables efficient C–C bond formation with aryl and heteroaryl halides, offering enhanced functional group tolerance and compatibility with diverse reaction conditions. The trifluoromethyl-substituted arylboronate functions reliably in Suzuki-Miyaura coupling workflows, facilitating the construction of complex biaryl architectures common in pharmaceutical and agrochemical synthesis.

Synthesis

Route1
- 88-16-4
- In-stock
  
  73183-34-3
- ~90%
- In-stock
  
  1073339-21-5
References
- Yamamoto, Tetsuya; Morita, Tomoyuki; Takagi, Jun; Yamakawa, Tetsu Organic Letters, 2011 , vol. 13, # 21 p. 5766 - 5769
Route2
- 61676-62-8
- In-stock
  
  444-29-1
- ~90%
- In-stock
  
  1073339-21-5
References
- Demory, Emilien; Blandin, Veronique; Einhorn, Jacques; Chavant, Pierre Y. Organic Process Research and Development, 2011 , vol. 15, # 3 p. 710 - 716
Route3
- 98-08-8
- 25015-63-8
- ~%
- In-stock
  
  1073339-21-5
- In-stock
  
  325142-82-3
References
- Journal of the American Chemical Society, , vol. 122, # 51 p. 12868 - 12869

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-H312-H332
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P363

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

CAS No. 1073339-21-5

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