148892-97-1

Basic information

• Product Name: Borane, tris(3,4,5-trifluorophenyl)-
• CAS NO: 148892-97-1
• Molecular Formula: C18H6BF9
• Molecular Weight: 404.042
• Mol File: 148892-97-1.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 349.7±42.0 °C(Predicted)
• Density: 1.47±0.1 g/cm3(Predicted)
• CAS DataBase Reference: Borane, tris(3,4,5-trifluorophenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Borane, tris(3,4,5-trifluorophenyl)-(148892-97-1)
• EPA Substance Registry System: Borane, tris(3,4,5-trifluorophenyl)-(148892-97-1)

Safety Data

• Hazardous Substances Data: 148892-97-1(Hazardous Substances Data)

Upstream product

• 138526-69-9 3,4,5-trifluoro-1-bromobenzene 
• 109-63-7 boron trifluoride diethyl etherate 

Downstream Products

• 184044-79-9 tris(3,4,5-trifluorophenyl)boron-tert-butylphosphine adduct 
• 36779-17-6 methyl 2-phenyl-1H-indole-3-carboxylate 

Relevant articles and documents

Lewis Acidic Boranes, Lewis Bases, and Equilibrium Constants: A Reliable Scaffold for a Quantitative Lewis Acidity/Basicity Scale

A quantitative Lewis acidity/basicity scale toward boron-centered Lewis acids has been developed based on a set of 90 experimental equilibrium constants for the reactions of triarylboranes with various O-, N-, S-, and P-centered Lewis bases in dichloromethane at 20 °C. Analysis with the linear free energy relationship log KB=LAB+LBB allows equilibrium constants, KB, to be calculated for any type of borane/Lewis base combination through the sum of two descriptors, one for Lewis acidity (LAB) and one for Lewis basicity (LBB). The resulting Lewis acidity/basicity scale is independent of fixed reference acids/bases and valid for various types of trivalent boron-centered Lewis acids. It is demonstrated that the newly developed Lewis acidity/basicity scale is easily extendable through linear relationships with quantum-chemically calculated or common physical–organic descriptors and known thermodynamic data (ΔH (Formula presented.)). Furthermore, this experimental platform can be utilized for the rational development of borane-catalyzed reactions.

1,3-Carboboration of iodonium ylides

Herein, we disclose the utilisation of iodonium ylides to access a range of boron dienolates. Heating of acyclic iodonium ylides in the presence of different aryl boranes leads to the formation of rare 1,3-carboboration products. This methodology could not be expanded to cyclic iodonium ylides which instead formed a Lewis acid-base adduct. Products proved to be remarkably stable under a wide range of conditions allowing for their long term storage.

Metal-Free Tandem Rearrangement/Lactonization: Access to 3,3-Disubstituted Benzofuran-2-(3H)-ones

A novel metal-free synthesis of 3,3-disubstituted benzofuran-2-(3H)-ones through reacting α-aryl-α-diazoacetates with triarylboranes is presented. Initially, triarylboranes were successfully investigated in α-arylations of α-diazoacetates, however in the presence of a heteroatom in the ortho position, the boron enolate intermediate undergoes an intramolecular rearrangement to form a quaternary center. The intermediate cyclizes to afford valuable 3,3-disubstituted benzofuranones in good yields.