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

Melting point:

310℃

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO (Slightly)

form 

Powder

color 

tan

Water Solubility 

soluble

BRN 

5474788

InChIKey

LTGMONZOZHXAHO-UHFFFAOYSA-N

SMILES

[B-](C1=CC(=CC(C(F)(F)F)=C1)C(F)(F)F)(C1=CC(=CC(C(F)(F)F)=C1)C(F)(F)F)(C1=CC(=CC(C(F)(F)F)=C1)C(F)(F)F)C1C=C(C=C(C(F)(F)F)C=1)C(F)(F)F.[Na+]

CAS DataBase Reference

79060-88-1

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

36/37/38-20/21/22

Safety Statements 

36/37/39-26-22

WGK Germany 

3

F 

10

TSCA 

No

HazardClass 

IRRITANT

HS Code 

29319090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

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

Chemical Properties

Light beige powder

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.

Uses

Sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate was used in the preparation of poly(n-butyl acrylate)- based ion-selective membranes.

General Description

Visit our Sensor Applications portal to learn more.

reaction suitability

core: sodium
reagent type: catalyst

Synthesis

The general procedure for the synthesis of sodium tetrakis(3,5-bis(trifluoromethyl)phenyl)borate from sodium fluoborate and 3,5-bis(trifluoromethyl)bromobenzene was as follows: first, a three-necked round-bottomed flask fitted with a reflux condenser was evacuated, flame-dried and replaced with argon. Subsequently, 1.01 g (41.7 mmol) of magnesium shavings, 0.72 g (6.4 mmol, 1 equiv.) of sodium fluoborate (NaBF4) and 150 mL of anhydrous ether were added to the flask. To initiate the reaction, 1.07 g (0.49 mL, 5.7 mmol, 0.9 eq.) of dibromoethane was added, and after heating the flask slightly for a few minutes, 1.71 g (6.25 mL, 36 mmol) of 3,5-bis(trifluoromethyl)bromobenzene was slowly added dropwise. After 30 minutes of reaction, the reaction mixture was diluted with 50 mL of ether. After the exothermic reaction slowed down, the reaction mixture was continued to be heated for 30 minutes. Subsequently, the reaction solution was stirred at room temperature overnight. Upon completion of the reaction, 16 g of sodium carbonate (Na2CO3) was added to 200 mL of distilled water to quench the reaction, stirred for 30 minutes and then filtered. The aqueous phase was extracted three times with 50 mL of ether, the organic phases were combined and dried with anhydrous sodium sulfate and activated carbon, and filtered. The solvent was removed under reduced pressure and the residual crude product was dissolved in 200 mL of toluene and the water was removed by azeotropic boiling through a Dean-Stark water separator. The solvent was again removed under reduced pressure, the product was filtered, washed with anhydrous toluene and dried under vacuum to give 4.65 g (5.3 mmol, 82% yield) of a colorless solid product with melting point decomposition >290 °C. The product was subjected to 1H-NMR (300 MHz, DMSO-d6), 13C-NMR (75.5 MHz, DMSO-d6), 19F-NMR (283 MHz, DMSO-d6) and elemental analysis to confirm the structure. Elemental analysis (C32H12BF24Na-1.8H2O) Calculated value: C=41.61, H=1.70; measured value: C=41.57, H=1.66.

References

[1] Inorganic Chemistry, 2014, vol. 54, # 1, p. 359 - 369
[2] Inorganic Chemistry, 2014, vol. 54, # 1, p. 359 - 369
[3] Tetrahedron Letters, 2016, vol. 57, # 31, p. 3453 - 3456
[4] Organic Syntheses, 2008, vol. 85, p. 248 - 266
[5] Journal of the American Chemical Society, 2001, vol. 123, # 44, p. 11020 - 11028

Sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate(79060-88-1)Related Product Information

• Phenylhydrazine
• Silicone oil (high temperature)
• Zinc borate
• Trimethyl borate
• PHENYL VALERATE
• Sodium tetraborate
• Tri(o-tolyl)phosphine
• Chlorodimethylphenylsilane
• TETRAPHENYLOLETHANE GLYCIDYL ETHER
• Tetrapropoxysilane
• 1,1,2,2-Tetrakis(4-bromophenyl)ethene
• Tetraphenylmethane
• PENTAERYTHRITOL TETRA(3-MERCAPTOPROPIONATE)
• Borate(1-), tetrakis[3,5-bis(trifluoroMethyl)phenyl]-, sodiuM, hydrate (9CI)
• Potassium chloride
• Sodium tetraphenylboron
• Sodium borohydride
• methylphenyl silicone resin