1162257-58-0 | 5-(trifluoromethyl)pyridin-2-ylboronic acid

CAS:1162257-58-0 | 5-(trifluoromethyl)pyridin-2-ylboronic acid,Description

5-(Trifluoromethyl)pyridine-2-boronic acid is a boronic acid derivative with a trifluoromethyl group and a pyridine ring. It is related to other boronic acids and pyridine compounds that have been studied for their chemical properties and potential applications in organic synthesis and catalysis.

Synthesis Analysis

The synthesis of related boronic acid compounds involves the use of halogenated pyridines as starting materials. For instance, the synthesis of 2-chloro-5-trifluoromethyl pyridine-4-yl-boronic acid was achieved using 2-chloro-4-iodo-5-trifluoromethyl pyridine, reacting with n-butyl lithium reagent under controlled conditions to yield a product with high purity and yield. This suggests that similar methodologies could be applied to synthesize 5-(Trifluoromethyl)pyridine-2-boronic acid.

Molecular Structure Analysis

The molecular structure of boronic acid derivatives is often characterized using techniques such as IR, NMR, and X-ray diffraction. For example, the structure of (3-(pyrrolidine-1-yl)-5-(trifluoromethyl)phenyl)boronic acid was confirmed by X-ray diffraction, and its electronic structure was analyzed using DFT, showing consistency between the optimized DFT structure and the crystal structure. This indicates that 5-(Trifluoromethyl)pyridine-2-boronic acid could also be analyzed using similar methods to understand its molecular conformation and electronic properties.

Chemical Reactions Analysis

Boronic acids are known to participate in various chemical reactions, including catalytic processes. Tris(pentafluorophenyl)borane, a related boron Lewis acid, has been used in catalytic hydrometallation reactions, alkylations, and aldol-type reactions. Additionally, 2,4-bis(trifluoromethyl)phenylboronic acid has been used as a catalyst for dehydrative amidation between carboxylic acids and amines. These studies suggest that 5-(Trifluoromethyl)pyridine-2-boronic acid could also be involved in similar chemical transformations.

Physical and Chemical Properties Analysis

The physical and chemical properties of boronic acids and their derivatives can be influenced by their molecular structures. For example, the crystal structure of 5-(trifluoromethyl)picolinic acid monohydrate reveals a water-bridged hydrogen-bonding network, which is important for understanding the compound's solubility and reactivity. The molecular structures of pyridine complexes with boron trifluoride, boron trichloride, and boron tribromide have been studied by gas phase electron diffraction, providing insights into the bonding interactions and geometries of these complexes. These findings can be extrapolated to predict the behavior of 5-(Trifluoromethyl)pyridine-2-boronic acid in various environments.

Scientific Research Applications

Suzuki–Miyaura Coupling

• Scientific Field : Organic Chemistry
• Application Summary : 5-(Trifluoromethyl)pyridine-2-boronic acid is used as a boron reagent in the Suzuki–Miyaura (SM) cross-coupling reaction. This reaction is a widely-applied transition metal catalyzed carbon–carbon bond forming reaction.
• Methods of Application : The SM coupling reaction conjoins chemically differentiated fragments that participate in electronically divergent processes with the metal catalyst. Oxidative addition occurs with formally electrophilic organic groups, whereby palladium becomes oxidized through its donation of electrons to form the new Pd–C bond.
• Results or Outcomes : The success of the SM coupling originates from a combination of exceptionally mild and functional group tolerant reaction conditions, with a relatively stable, readily prepared and generally environmentally benign organoboron reagent.

Synthesis of Trifluoromethylpyridines

• Scientific Field : Agrochemical and Pharmaceutical Industries
• Application Summary : Trifluoromethylpyridine (TFMP) and its derivatives, including 5-(Trifluoromethyl)pyridine-2-boronic acid, are key structural motifs in active agrochemical and pharmaceutical ingredients.
• Methods of Application : The synthesis and applications of TFMP derivatives are thought to be due to the combination of the unique physicochemical properties of the fluorine atom and the unique characteristics of the pyridine moiety.
• Results or Outcomes : More than 20 new TFMP-containing agrochemicals have acquired ISO common names. Five pharmaceutical and two veterinary products containing the TFMP moiety have been granted market approval, and many candidates are currently undergoing clinical trials.

Formation of Pyridyl Boronic Ester

• Scientific Field : Organic Chemistry
• Application Summary : 5-(Trifluoromethyl)pyridine-2-boronic acid is used as a key starting material for the formation of pyridyl boronic ester such as pyridine-2-boronic acid dimethyl ester.
• Methods of Application : The dimethyl ester reacts with bromquinoline to prepare the 2-pyridyl derivative of quinoline.
• Results or Outcomes : The product of this reaction is the 2-pyridyl derivative of quinoline.

Heterocyclization with α-Oxocarboxylic Acids

• Scientific Field : Organic Chemistry
• Application Summary : 5-(Trifluoromethyl)pyridine-2-boronic acid is used as a reactant in heterocyclization with α-oxocarboxylic acids.
• Methods of Application : The specific methods of application and experimental procedures would depend on the specific α-oxocarboxylic acid used and the desired product.
• Results or Outcomes : The outcome of this reaction is the formation of a heterocyclic compound.

Synthesis of Heteroaryl Benzylureas

• Scientific Field : Medicinal Chemistry
• Application Summary : 5-(Trifluoromethyl)pyridine-2-boronic acid is used as a precursor to biologically active molecules including heteroaryl benzylureas.
• Methods of Application : The specific methods of application and experimental procedures would depend on the specific heteroaryl benzylurea being synthesized.
• Results or Outcomes : Heteroaryl benzylureas synthesized using 5-(Trifluoromethyl)pyridine-2-boronic acid have been found to have glycogen synthase kinase 3 inhibitory activity.

Synthesis of Carboxyindoles

• Scientific Field : Medicinal Chemistry
• Application Summary : 5-(Trifluoromethyl)pyridine-2-boronic acid is used as a precursor to biologically active molecules including carboxyindoles.
• Methods of Application : The specific methods of application and experimental procedures would depend on the specific carboxyindole being synthesized.
• Results or Outcomes : Carboxyindoles synthesized using 5-(Trifluoromethyl)pyridine-2-boronic acid have been found to have HCV NS5B polymerase inhibitory activity.

Heterocyclization with α-Oxocarboxylic Acids

• Scientific Field : Organic Chemistry
• Application Summary : 5-(Trifluoromethyl)pyridine-2-boronic acid is used as a reactant in heterocyclization with α-oxocarboxylic acids.
• Methods of Application : The specific methods of application and experimental procedures would depend on the specific α-oxocarboxylic acid used and the desired product.
• Results or Outcomes : The outcome of this reaction is the formation of a heterocyclic compound.

Synthesis of Heteroaryl Benzylureas

• Scientific Field : Medicinal Chemistry
• Application Summary : 5-(Trifluoromethyl)pyridine-2-boronic acid is used as a precursor to biologically active molecules including heteroaryl benzylureas.
• Methods of Application : The specific methods of application and experimental procedures would depend on the specific heteroaryl benzylurea being synthesized.
• Results or Outcomes : Heteroaryl benzylureas synthesized using 5-(Trifluoromethyl)pyridine-2-boronic acid have been found to have glycogen synthase kinase 3 inhibitory activity.

Synthesis of Carboxyindoles

• Scientific Field : Medicinal Chemistry
• Application Summary : 5-(Trifluoromethyl)pyridine-2-boronic acid is used as a precursor to biologically active molecules including carboxyindoles.
• Methods of Application : The specific methods of application and experimental procedures would depend on the specific carboxyindole being synthesized.
• Results or Outcomes : Carboxyindoles synthesized using 5-(Trifluoromethyl)pyridine-2-boronic acid have been found to have HCV NS5B polymerase inhibitory activity.

Safety And Hazards

5-(Trifluoromethyl)pyridine-2-boronic acid causes skin irritation, serious eye irritation, and may cause respiratory irritation.

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