120153-08-4 | 4-Carboxy-3-fluorophenylboronic acid

CAS:120153-08-4 | 4-Carboxy-3-fluorophenylboronic acid,Description

Synthesis Analysis

The synthesis of derivatives similar to 4-carboxy-3-fluorophenylboronic acid often involves halogen-lithium exchange reactions, followed by the addition of trimethyl borate and subsequent hydrolysis. For instance, the synthesis of amino-3-fluorophenyl boronic acid was achieved through such a methodology, with a reported yield of 47% (Das et al., 2003). This process highlights the general approach to synthesizing boronic acid derivatives with specific substituents on the phenyl ring.

Molecular Structure Analysis

The molecular structure of boronic acid derivatives, including those with carboxy and fluorine substituents, has been extensively studied. For example, solid-state structures of 4-carboxyphenylboronic acid and its hydrates have been reported, demonstrating the impact of hydration on molecular conformation and intermolecular interactions. These studies reveal that hydrogen bonding plays a significant role in the crystal packing of these compounds, leading to diverse solid-state architectures (SeethaLekshmi & Pedireddi, 2007).

Chemical Reactions and Properties

Boronic acids, including 4-carboxy-3-fluorophenylboronic acid, are pivotal in organic synthesis, particularly in Suzuki coupling reactions. These reactions are essential for forming carbon-carbon bonds, thereby constructing complex molecular frameworks. The presence of fluorine and carboxy groups influences the reactivity and stability of the boronic acid, affecting its behavior in these coupling reactions.

Physical Properties Analysis

The physical properties of boronic acid derivatives are influenced by their molecular structure. For example, the hydration state of 4-carboxyphenylboronic acid affects its crystallization and, consequently, its physical appearance. The analysis of solid-state structures provides insights into the impact of substituents on the physical properties of these compounds.

Chemical Properties Analysis

The chemical properties of 4-carboxy-3-fluorophenylboronic acid are characterized by its reactivity in various chemical reactions, including its role as a catalyst or reactant in organic synthesis. The ortho-substituent on phenylboronic acids, such as in the case of 2,4-bis(trifluoromethyl)phenylboronic acid, has been shown to catalyze dehydrative condensation reactions between carboxylic acids and amines, indicating the influence of substituent positioning on chemical reactivity (Wang, Lu, & Ishihara, 2018).

Scientific Research Applications

• Glucose-Responsive Insulin

  • Field : Chemical Biology
  • Application : Phenylboronic acid-modified insulin has been developed for glucose-responsive insulin therapy.
  • Method : Attaching two fluorophenylboronic acid (FPBA) residues to the C-terminal B chain of insulin glargine led to glucose-dependent solubility.
  • Results : Relocating FPBA from B chain to A chain increased the baseline solubility without affecting its potency. Increasing the number of FPBA groups led to increased glucose-dependent solubility.

• Biomedical Applications

  • Field : Biomedical Research
  • Application : Phenylboronic acid-functionalized chitosan conjugates have been used in various biomedical applications.
  • Method : The conjugation of phenylboronic acid and its moieties with chitosan, a cationic polysaccharide, has shown to exhibit a plethora of properties that can be exploited for a variety of applications.
  • Results : These conjugates have been used as glucose-sensitive polymers for self-regulated insulin release in the treatment of diabetes, as a diagnostic agent, in wound healing, and tumor targeting.

• Condensation Reactions

  • Field : Polymer Chemistry
  • Application : 4-Carboxyphenylboronic acid has been used in condensation reactions with stabilizer chains at the surface of polystyrene latex.
  • Method : The specific methods of application or experimental procedures were not detailed in the source.
  • Results : The specific results or outcomes obtained were not detailed in the source.

• Synthesis of Novel Liquid Crystalline Fluorobiphenylcyclohexenes and Difluoroterphenyls

  • Field : Organic Chemistry
  • Application : 3-Fluorophenylboronic acid has been used to make novel liquid crystalline fluorobiphenylcyclohexenes and difluoroterphenyls.
  • Method : The specific methods of application or experimental procedures were not detailed in the source.
  • Results : The specific results or outcomes obtained were not detailed in the source.

• Synthesis of o-Phenylphenols

  • Field : Organic Chemistry
  • Application : 3-Fluorophenylboronic acid has been used in the synthesis of o-phenylphenols as potent leukotriene B4 receptor agonists.
  • Method : The specific methods of application or experimental procedures were not detailed in the source.
  • Results : The specific results or outcomes obtained were not detailed in the source.

• Suzuki Coupling Reactions

  • Field : Organic Chemistry
  • Application : 4-Fluorophenylboronic acid can be used as a reactant in coupling reactions with arenediazonium tetrafluoroborates, iodonium salts, and iodanes.
  • Method : The specific methods of application or experimental procedures were not detailed in the source.
  • Results : The specific results or outcomes obtained were not detailed in the source.

• Synthesis of Isotopically Labeled Mercury

  • Field : Inorganic Chemistry
  • Application : 4-Carboxyphenylboronic acid has been used in the synthesis of isotopically labeled mercury.
  • Method : The specific methods of application or experimental procedures were not detailed in the source.
  • Results : The specific results or outcomes obtained were not detailed in the source.

• Functionalization of Poly-SiNW for Detection of Dopamine

  • Field : Biochemistry
  • Application : 4-Carboxyphenylboronic acid has been used for the functionalization of poly-SiNW for the detection of dopamine.
  • Method : The specific methods of application or experimental procedures were not detailed in the source.
  • Results : The specific results or outcomes obtained were not detailed in the source.

• Suzuki Coupling Using Microwave and Triton B Catalyst

  • Field : Organic Chemistry
  • Application : 4-Fluorophenylboronic acid can be used as a reactant in Suzuki coupling using microwave and triton B catalyst.
  • Method : The specific methods of application or experimental procedures were not detailed in the source.
  • Results : The specific results or outcomes obtained were not detailed in the source.

Safety And Hazards

The safety information for 4-Carboxy-3-fluorophenylboronic acid includes hazard statements H315, H319, H335, indicating that it can cause skin irritation, serious eye irritation, and may cause respiratory irritation. Precautionary measures include avoiding breathing dust/fume/gas/mist/vapors/spray, washing hands thoroughly after handling, and wearing protective gloves/protective clothing/eye protection/face protection.

Future Directions

4-Carboxy-3-fluorophenylboronic acid has been used in the synthesis of glucose-responsive 4-carboxy-3-fluorophenylboronic acid-grafted ε-polylysine (CFPBA- g -PL) for glucose-responsive insulin delivery via transdermal microneedles. This represents a promising direction for the application of this compound in the field of diabetes management.

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