659-18-7 | TRIS(2,2,2-TRIFLUOROETHYL) BORATE

CAS:659-18-7 | TRIS(2,2,2-TRIFLUOROETHYL) BORATE,Description

Tris(2,2,2-trifluoroethyl) borate, also commonly referred to as the Sheppard amidation reagent, is a chemical compound with the formula B(OCH2CF3)3 . This borate ester reagent is used in organic synthesis . It is mostly used in condensation reactions and has been shown to promote the direct formation of amides from carboxylic acids and amines as well as the formation of imines from amines or amides with carbonyl compounds .

Synthesis Analysis

Tris(2,2,2-trifluoroethyl) borate can be prepared by the reaction of trifluoroethanol with boron trichloride, borane dimethylsulfide, boron tribromide, or boric anhydride . The product is purified by distillation . An experimental procedure involves adding a solution of tris(2,2,2-trifluoroethyl) borate in CPME to a mixture of an unprotected amino acid and propylamine in CPME over 1 hour at 80°C or 125°C. The resulting mixture is stirred for 5 - 15 hours .

Molecular Structure Analysis

The molecular formula of Tris(2,2,2-trifluoroethyl) borate is C6H6BF9O3 . Its molecular weight is 307.91 .

Chemical Reactions Analysis

Tris(2,2,2-trifluoroethyl) borate is used in condensation reactions. It promotes the direct formation of amides from carboxylic acids and amines as well as the formation of imines from amines or amides with carbonyl compounds .

Physical And Chemical Properties Analysis

Tris(2,2,2-trifluoroethyl) borate is a colorless liquid . It has a density of 1.430 g/cm3 and a boiling point of 94.3°C . Its refractive index is 1.298 .

Scientific Research Applications

4. Coupling of Unprotected Amino Acids with Amines

• Summary of Application: Tris(2,2,2-trifluoroethyl) borate has been used for the coupling of unprotected amino acids with amines .

5. Formylation of Amines

• Summary of Application: Tris(2,2,2-trifluoroethyl) borate has been shown to mediate formylation of amines, via transamidation of dimethylformamide .

6. Lewis Acid

• Summary of Application: Tris(2,2,2-trifluoroethyl) borate is a strong Lewis acid (acceptor number = 66, Gutmann-Beckett method) .

7. Selective Beta1 Adrenergic Receptor Blocker

• Summary of Application: Tris(2,2,2-trifluoroethyl) borate is used as a selective beta1 adrenergic receptor blocker .
• Methods of Application: The compound is used in the treatment of hypertension and glaucoma .
• Results: The use of Tris(2,2,2-trifluoroethyl) borate in these treatments has been shown to be effective .

8. Transamidation of Dimethylformamide

• Summary of Application: Tris(2,2,2-trifluoroethyl) borate has been shown to mediate formylation of amines, via transamidation of dimethylformamide .
• Methods of Application: The compound is used as a reagent in these reactions, promoting the formation of the desired products .
• Results: The use of Tris(2,2,2-trifluoroethyl) borate in these reactions has been shown to be effective, leading to the successful formation of the desired products .

9. High-Concentration Electrolytes in Lithium Metal Batteries

• Summary of Application: Tris(2,2,2-trifluoroethyl) borate has been investigated for its effects on electrolyte solvation structures and electrode/electrolyte interphases in lithium metal batteries .
• Methods of Application: The study involved the comparison of different types of fluorinated solvents in high-concentration electrolytes (HCEs), including Tris(2,2,2-trifluoroethyl) borate .
• Results: The study found that the type of diluent used in the electrolyte can significantly influence the performance of the battery .

Safety And Hazards

Tris(2,2,2-trifluoroethyl) borate is classified as a flammable liquid and vapor . It is recommended to avoid contact with skin and eyes, avoid formation of dust and aerosols, and provide appropriate exhaust ventilation at places where dust is formed . In case of fire, use dry sand, dry chemical or alcohol-resistant foam to extinguish .

Future Directions

While Tris(2,2,2-trifluoroethyl) borate is already used in various chemical reactions, there is potential for further exploration of its uses. For instance, Lithium cyano tris(2,2,2-trifluoroethyl) borate has been synthesized and investigated as a new electrolyte additive for high-performance lithium metal batteries .

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