Sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate

Base Information

• Chemical Name: Sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate
• CAS No.: 79060-88-1
• Molecular Formula: C32H12BF24Na
• Molecular Weight: 886.21
• Hs Code.: 29319090
• Mol file: 79060-88-1.mol

Synonyms:Borate(1-),tetrakis[3,5-bis(trifluoromethyl)phenyl]-, sodium (9CI);Sodiumtetrakis(3,5-bis(trifluoromethyl)phenyl)borate(1-);Sodiumtetrakis[3,5-bis(trifluoromethyl)phenyl]borate;Tetrakis[3,5-bis(trifluoromethyl)phenyl]borate sodium salt;

Chemical Property of Sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate

Chemical Property:

• Appearance/Colour: Light beige powder
• Melting Point: 310℃
• PSA: 0.00000
• LogP: 11.21440
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly)
• Water Solubility.: soluble

Purity/Quality:

97% ^*data from raw suppliers

Sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 36/37/38-20/21/22
• Safety Statements: 36/37/39-26-22

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate, also known as the BARF anion, is a compound used in catalytic cycles due to its inability to coordinate to metal centres. Sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate was used in the preparation of poly(n-butyl acrylate)- based ion-selective membranes.

Technology Process of Sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate

There total 8 articles about Sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

sodium tetrafluoroborate (13755-29-8) + 3,6-bis(trifluoromethyl)bromobenzene (328-70-1) → sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate (79060-88-1)

Guidance literature:

With magnesium; In diethyl ether; ethylene dibromide; Inert atmosphere; Schlenk technique; Reflux;

DOI:10.1021/acs.inorgchem.1c00042

Reference yield: 78.0%

3,6-bis(trifluoromethyl)bromobenzene (328-70-1) → sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate (79060-88-1)

Guidance literature:

With sodium tetrafluoroborate; magnesium; ethylene dibromide; In diethyl ether; Reflux;

DOI:10.1002/chem.202101961

Reference yield: 68.0%

3,6-bis(trifluoromethyl)bromobenzene (328-70-1) + boron trifluoride diethyl etherate (109-63-7) + sodium carbonate (497-19-8) → sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate (79060-88-1)

Guidance literature:

3,6-bis(trifluoromethyl)bromobenzene; With iodine; magnesium; In diethyl ether; at 20 ℃; for 4h;

boron trifluoride diethyl etherate; In diethyl ether; at 40 ℃; for 12h;

sodium carbonate; In diethyl ether; water;

DOI:10.1039/c9dt00235a

upstream raw materials:

3,6-bis(trifluoromethyl)bromobenzene

sodium carbonate

sodium tetrafluoroborate

sodium tetrakis[3,5-bis-(trifluoromethyl)phenyl]borate dihydrate

Downstream raw materials:

4-fluoro-3'-trifluoromethylbenzophenone

CH₂CCH₃CH₂OP(N(CH₃)2)3⁽¹⁺⁾*B(C₆H₃(CF₃)2)4^(1-)=CH₂CCH₃CH₂OP(N(CH₃)2)3B(C₆H₃(CF₃)2)4

Refernces

Ligand-Promoted Alkynylation of Aryl Ketones: A Practical Tool for Structural Diversity in Drugs and Natural Products

10.1021/acscatal.0c05372

The study presents a novel palladium-catalyzed ligand-promoted alkynylation of aryl ketones. The protocol involves the conversion of aryl ketones into aryl electrophiles via Ar-C(O) cleavage, a challenging transformation in Sonogashira-type coupling. The key chemicals involved include aryl ketones as the starting materials, alkynylsilanes as the coupling partners, and a palladium catalyst along with a ligand, specifically a pyridine-oxazoline ligand (L32), which plays a crucial role in promoting the reaction. The reaction also utilizes potassium carbonate (K2CO3) as a base and sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate (NaBArF) as an additive. The process is carried out in a one-pot procedure, demonstrating broad functional-group tolerance and substrate scope. The study highlights the potential applications of this protocol in drug discovery and chemical biology by showcasing the late-stage diversification of pharmaceuticals and natural products. The method allows for the 1,2-bifunctionalization of aryl ketones, merging ketone-directed ortho-C-H activation with ligand-promoted ipso-Ar-C(O) alkynylation, providing a practical tool for the synthesis of biologically important molecules.