143418-49-9 | 3,4,5-Trifluorophenylboronic acid

CAS:143418-49-9 | 3,4,5-Trifluorophenylboronic acid,Description

3,4,5-Trifluorophenylboronic acid is a biochemical reagent that can be used as a biological material or organic compound for life science related research. It is a white to light brown crystalline powder.

Synthesis Analysis

The synthesis of 3,4,5-Trifluorophenylboronic acid involves a Grignard reaction. After the reaction is initiated, the temperature rises rapidly and is then lowered to 10-15°C in an ice-water bath. The reaction continues at room temperature for 8 hours. After the reaction is over, the reaction solution is slowly poured into dilute hydrochloric acid. The liquids are then separated, and the aqueous phase is extracted twice. The organic phases are combined, dried with anhydrous sodium sulfate, spin dried, and recrystallized from ethyl chloride. This process yields 3,4,5-Trifluorophenylboronic acid with a yield of 78% and a content of 99.6%.

Molecular Structure Analysis

The molecular formula of 3,4,5-Trifluorophenylboronic acid is C6H4BF3O2. The molecular weight is 175.903 g/mol.

Chemical Reactions Analysis

3,4,5-Trifluorophenylboronic acid is involved in several chemical reactions. It is used in the preparation of phenylboronic catechol esters and determination of Lewis acidity. It is also used in the synthesis of benzopyranone derivatives as GABAA receptor modulators, synthesis of multisubstituted olefins and conjugate dienes, and Suzuki cross-coupling reactions.

Physical And Chemical Properties Analysis

3,4,5-Trifluorophenylboronic acid has a density of 1.4±0.1 g/cm^3. Its melting point is 290-295 °C (lit.), and its boiling point is 263.6±50.0 °C at 760 mmHg. The vapour pressure is 0.0±0.6 mmHg at 25°C.

Scientific Research Applications

Preparation of Phenylboronic Catechol Esters

• Scientific Field : Organic Chemistry
• Application Summary : 3,4,5-Trifluorophenylboronic acid is used in the preparation of phenylboronic catechol esters.
• Results or Outcomes : The outcome of this application is the formation of phenylboronic catechol esters.

Synthesis of Benzopyranone Derivatives

• Scientific Field : Medicinal Chemistry
• Application Summary : 3,4,5-Trifluorophenylboronic acid is used in the synthesis of benzopyranone derivatives, which are known to be GABAA receptor modulators.
• Methods of Application : The synthesis typically involves a reaction between the boronic acid and other reagents to form the benzopyranone structure.
• Results or Outcomes : The result is the formation of benzopyranone derivatives, which can modulate GABAA receptors.

Synthesis of Multisubstituted Olefins and Conjugate Dienes

• Scientific Field : Organic Chemistry
• Application Summary : 3,4,5-Trifluorophenylboronic acid is used in the synthesis of multisubstituted olefins and conjugate dienes.
• Methods of Application : The synthesis typically involves a reaction between the boronic acid and other reagents to form the desired olefin or diene structure.
• Results or Outcomes : The result is the formation of multisubstituted olefins and conjugate dienes.

Suzuki Cross-Coupling Reactions

• Scientific Field : Organic Chemistry
• Application Summary : 3,4,5-Trifluorophenylboronic acid is used in Suzuki cross-coupling reactions.
• Methods of Application : The Suzuki reaction is a type of palladium-catalyzed cross-coupling reaction, which involves the reaction of an aryl- or vinyl-boronic acid with an aryl- or vinyl-halide.
• Results or Outcomes : The result is the formation of a new carbon-carbon bond, linking the two reactants.

Direct Amidation of Amino Acid Derivatives

• Scientific Field : Biochemistry
• Application Summary : 3,4,5-Trifluorophenylboronic acid can be used as a catalyst to catalyse the direct amidation of amino acid derivatives.
• Methods of Application : The process typically involves the reaction of the boronic acid with amino acid derivatives in the presence of a suitable catalyst.
• Results or Outcomes : The result is the formation of amide bonds, which are crucial in the formation of peptides and proteins.

Preparation of Fluorinated Aromatic Poly (Ether-Amide)s

• Scientific Field : Polymer Chemistry
• Application Summary : 3,4,5-Trifluorophenylboronic acid is used in the preparation of fluorinated aromatic poly (ether-amide)s.
• Methods of Application : The synthesis typically involves a reaction between the boronic acid and other reagents to form the desired polymer structure.
• Results or Outcomes : The result is the formation of fluorinated aromatic poly (ether-amide)s.

Catalyst for Direct Amidation of Amino Acid Derivatives

• Scientific Field : Biochemistry
• Application Summary : 3,4,5-Trifluorophenylboronic acid can be used as a catalyst to catalyse the direct amidation of amino acid derivatives.
• Methods of Application : The process typically involves the reaction of the boronic acid with amino acid derivatives in the presence of a suitable catalyst.
• Results or Outcomes : The result is the formation of amide bonds, which are crucial in the formation of peptides and proteins.

Direct Polycondensation of Carboxylic Acids and Amines

• Scientific Field : Polymer Chemistry
• Application Summary : 3,4,5-Trifluorophenylboronic acid can be used in the direct polycondensation of carboxylic acids and amines.
• Methods of Application : The synthesis typically involves a reaction between the boronic acid, carboxylic acids, and amines to form the desired polymer structure.
• Results or Outcomes : The result is the formation of new polymers.

Safety And Hazards

3,4,5-Trifluorophenylboronic acid is considered hazardous by the 2012 OSHA Hazard Communication Standard (29 CFR 1910.1200). It is harmful if swallowed and causes serious eye irritation. It is recommended to wear personal protective equipment/face protection and ensure adequate ventilation when handling this chemical.

Future Directions

3,4,5-Trifluorophenylboronic acid has been used in the preparation of phenylboronic catechol esters and determination of Lewis acidity, synthesis of benzopyranone derivatives as GABAA receptor modulators, synthesis of multisubstituted olefins and conjugate dienes, and Suzuki cross-coupling reactions. These applications suggest that it could have potential uses in various fields of chemistry and materials science.

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Uses