4-Formylphenylboronic acid

• CAS: 87199-17-5
• Catalog Number: ACM87199175-2
• Category: Main Products
• Molecular Weight: 149.94
• Molecular Formula: C7H7BO3
• Synonyms: Boronic acid, B-(4-formylphenyl)-
• IUPAC Name: (4-formylphenyl)boronic acid
• Canonical SMILES: B(C1=CC=C(C=C1)C=O)(O)O
• InChI: InChI=1S/C7H7BO3/c9-5-6-1-3-7(4-2-6)8(10)11/h1-5,10-11H
• InChI Key: VXWBQOJISHAKKM-UHFFFAOYSA-N
• Boiling Point: 347.6±44.0 °C
• Melting Point: 237-242 °C (lit.)
• Flash Point: 164.013ºC
• Density: 1.24±0.1 g/ml
• Appearance: off-white powder
• Application: 4-Formylphenylboronic acid, appearing as a white to light yellow crystal powder, plays a crucial role in various chemical reactions and applications. Primarily utilized as a substrate in Suzuki cross-coupling reactions, it facilitates palladium-catalyzed Suzuki-Miyaura cross-couplings in aqueous environments. This versatile compound also participates in copper-mediated, ligandless aerobic fluoroalkylation of arylboronic acids with fluoroalkyl iodides, and ligand-free copper-catalyzed coupling of nitro arenes with arylboronic acids. It is effective in triethylamine-catalyzed three-component Hantzsch condensations and copper-catalyzed nitrations, and it aids in the oxidative mono-cleavage of dialkenes, catalyzed by Trametes hirsuta. Additionally, it contributes to palladacycle-catalyzed cross-couplings of arylboronic acids with carboxylic anhydrides or acyl chlorides, and palladium-catalyzed aerobic oxidative cross-couplings. Its utility extends to synthesizing sensitizers featuring dithiafulvenyl units for high-efficiency dye-sensitized solar cells, developing novel protein synthesis inhibitors effective against Gram-positive bacteria, and conducting Suzuki aryl-aryl couplings on hexahomotrioxacalix[3]arene. Furthermore, it enables rhodium-catalyzed cyclizations that transform 1,5-enynes into cyclopentenes and spiro-cyclopentenes.
• EC Number: 617-982-7
• Exact Mass: 150.04900
• Hazard Statements: C:Corrosive
• Safety Description: S22-S26-S37/39-S45
• WGK Germany: 3

Case Study

4-Formylphenylboronic Acid for the Synthesis of Glucose-Responsive Chitosan Hydrogels

DAMIRI F, et al. Chinese Journal of Analytical Chemistry, 2022, 50(7), 100092.

n this study, 4-formylphenylboronic acid (4-FPBA) was employed to synthesize a glucose-responsive hydrogel via Schiff base chemistry, demonstrating superior physiological stability compared to conventional phenylboronic acid derivatives. The hydrogel was constructed by cross-linking 4-FPBA with chitosan, a biocompatible polysaccharide bearing amino functionalities. Experimentally, 1 g of chitosan was dissolved in 60 mL of 1% (v/v) acetic acid and subsequently diluted with 30 mL ethanol under stirring at 0 °C for 1 hour. Separately, 0.460 g of 4-FPBA was solubilized in 10 mL ethanol and gradually introduced into the chitosan solution under continuous agitation for an additional hour at 0 °C. The mixture was then neutralized to pH 7 using 6% (w/v) sodium bicarbonate, facilitating gelation and the formation of a translucent hydrogel. The cross-linking occurred via Schiff base formation between the aldehyde group of 4-FPBA and the amine groups on chitosan, yielding a -C=N- linkage. This boronated hydrogel exhibited glucose sensitivity, indicating its promising application in stimuli-responsive insulin delivery systems under physiological conditions.

4-Formylphenylboronic Acid for the Fabrication of Au-ATP-BA Self-Assembled Monolayer Electrodes

Zhao Y. Q., et al. Sensors and Actuators B: Chemical, 2009, 137(2), 722-726.

This protocol highlights the experimental application of 4-formylphenylboronic acid as a critical linker in the surface modification of gold electrodes, enabling precise molecular assembly through covalent conjugation strategies.
4-formylphenylboronic acid was employed for the functionalization of gold electrodes via the formation of a self-assembled monolayer (SAM). The procedure began with the mechanical polishing of the Au electrode using alumina slurry (0.3 to 0.05 μm), followed by thorough rinsing and chemical cleaning in piranha solution (H₂SO₄:H₂O₂ = 3:1) to remove organic contaminants. After ultrasonic cleaning in water and ethanol, the electrode was electrochemically cycled in 0.5 M H₂SO₄ until a stable cyclic voltammogram was achieved, ensuring surface stability.
The cleaned electrode was subsequently immersed in a 22.4 mM aqueous solution of p-aminothiophenol (p-ATP) in darkness for 5 hours at room temperature to establish a monolayer through Au-S bonding. This Au-ATP modified surface was then reacted with 4-formylphenylboronic acid in 1,4-dioxane at 40 °C for 90 minutes. The functionalization occurred via in situ Schiff base condensation between the amine group of p-ATP and the aldehyde moiety of 4-formylphenylboronic acid, resulting in the formation of a well-ordered Au-ATP-BA SAM.

Custom Q&A

What is the molecular formula of 4-Formylphenylboronic acid?

The molecular formula of 4-Formylphenylboronic acid is C7H7BO3.

What is the molecular weight of 4-Formylphenylboronic acid?

The molecular weight of 4-Formylphenylboronic acid is 149.94 g/mol.

What is the IUPAC name of 4-Formylphenylboronic acid?

The IUPAC name of 4-Formylphenylboronic acid is (4-formylphenyl)boronic acid.

What is the InChI of 4-Formylphenylboronic acid?

The InChI of 4-Formylphenylboronic acid is InChI=1S/C7H7BO3/c9-5-6-1-3-7(4-2-6)8(10)11/h1-5,10-11H.

What is the InChIKey of 4-Formylphenylboronic acid?

The InChIKey of 4-Formylphenylboronic acid is VXWBQOJISHAKKM-UHFFFAOYSA-N.

What is the canonical SMILES notation for 4-Formylphenylboronic acid?

The canonical SMILES notation for 4-Formylphenylboronic acid is B(C1=CC=C(C=C1)C=O)(O)O.

What is the CAS number for 4-Formylphenylboronic acid?

The CAS number for 4-Formylphenylboronic acid is 87199-17-5.

How many hydrogen bond donor counts are in 4-Formylphenylboronic acid?

There are 2 hydrogen bond donor counts in 4-Formylphenylboronic acid.

What is the topological polar surface area of 4-Formylphenylboronic acid?

The topological polar surface area of 4-Formylphenylboronic acid is 57.5Ų.

How many covalently-bonded unit counts are in 4-Formylphenylboronic acid?

There is 1 covalently-bonded unit count in 4-Formylphenylboronic acid.