4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde

• CAS: 128376-64-7
• Catalog Number: ACM128376647-1
• Category: Main Products
• Molecular Weight: 232.10
• Molecular Formula: C₁₃H₁₇BO₃
• Synonyms: BM087, 4-Formylphenylboronic acid pinacol ester, 128376-64-7
• IUPAC Name: 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde
• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=C(C=C2)C=O
• InChI Key: DMBMXJJGPXADPO-UHFFFAOYSA-N
• Boiling Point: 341.3ºC at 760 mmHg
• Melting Point: 55-58ºC
• Flash Point: 160.2ºC
• Density: 1.06g/cm³
• Appearance: Light yellow powder
• Exact Mass: 232.12700
• Hazard Statements: Xi
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Safety Description: 26-36/37/39

Case Study

Electronic Properties of 4-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Benzaldehyde Studied by DFT

Guevara, Ulises J., et al. International Journal of Molecular Sciences, 2024, 25(9), 5000.

Density functional theory (DFT) was used to analyze the UV-visible and IR spectra as well as the isotropic shielding and chemical shifts of hydrogen atoms 1H, carbon 13C and boron 11B in the compound 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde (ABP). In addition, the changes in the electronic and spectral properties of this particular ester when the boron atom is coordinated with the fluoride anion are considered. The important conclusions include:
· In NMR spectroscopy, fluorine coordinated with boron affects the shielding and unshielding of certain atoms, changing the electronic density.
· The UV-vis absorption spectra of the ABPF anion show a shift in their π → π* transitions, indicating how fluorine impacts the compound's electronic structure and light absorption.
IR spectroscopy reveals that C-H and C=O vibrations remain mostly unchanged after fluorination, while C=C, B-C bonds, and BO2 bending vibrations shift due to fluorine coordination.
· The B3LYP functional theoretical approach accurately predicts these changes and can be used to design new boronate compounds.
· The boron atom in the ABP compound acts as a Lewis acid and can form stable anions by binding with fluoride ions, altering their optical and spectral properties. This characteristic could make the ABP compound a useful marker for fluoride ions.

Synthesis of PEG-Lipid Conjugate with 4-Formylphenylboronic Acid Pinacol Ester for Drug Delivery

Zhang, Tianhui, et al. Polymer Chemistry, 2017, 8(40), 6209-6216.

A phenylboronic acid ester-linked PEG-lipid conjugate (mPEG2k-PBPE-DSA) was designed and synthesized, which can self-assemble into stable micelles in aqueous media, exhibit typical H2O2-responsive drug release behavior, and can be effectively internalized by MCF-7 cells. In addition, the experimental results showed that the biocompatible mPEG2k-PBPE-DSA was non-toxic to RAW264.7 cells and was expected to be applied in ROS-responsive drug delivery.
Synthesis procedure of mPEG2k-PBPE-DSA
· A combination of carboxylic acid terminated poly(ethylene glycol) methyl ether, 4-formylphenylboronic acid pinacol ester, and propargyl isocyanoacetamide in THF was stirred at 65 °C for 3 days. The resulting mixture was precipitated into diethyl ether three times. The polymer, named mPEG2k-PBPE-alkynyl, was obtained as a white powder after vacuum drying overnight, yielding 87%.
· Subsequently, a mixture of mPEG2k-PBAPE-alkynyl and 3-azido-1,2-propanediol distearate in THF was combined with a solution of CuSO4·5H2O and sodium ascorbate in deionized water. After three freeze-vacuum-thaw cycles, the mixture was stirred at room temperature for 24 hours. After dialysis in EDTA·2Na aqueous solution and ultrapure water for 3 days, mPEG2kPBPE-DSA was obtained after freeze-drying and reprecipitation in anhydrous ether to obtain a brown powdery solid with a yield of 65.5%.

Custom Q&A

What is the molecular formula of the compound?

The molecular formula is C13H17BO3.

What are the synonyms of the compound?

The synonyms are 128376-64-7, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde, 4-Formylphenylboronic acid pinacol ester, 4-Formylphenylboronic acid, pinacol ester, and 4-formylphenylboronic acid pinacolate.

What is the molecular weight of the compound?

The molecular weight is 232.09 g/mol.

When was the compound created and modified?

The compound was created on July 19, 2005, and last modified on October 21, 2023.

What is the IUPAC name of the compound?

The IUPAC name is 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde.

What is the InChI of the compound?

The InChI is InChI=1S/C13H17BO3/c1-12(2)13(3,4)17-14(16-12)11-7-5-10(9-15)6-8-11/h5-9H,1-4H3.

What is the InChIKey of the compound?

The InChIKey is DMBMXJJGPXADPO-UHFFFAOYSA-N.

What is the Canonical SMILES of the compound?

The Canonical SMILES is B1(OC(C(O1)(C)C)(C)C)C2=CC=C(C=C2)C=O.

What is the CAS number of the compound?

The CAS number is 128376-64-7.

What is the topological polar surface area of the compound?

The topological polar surface area is 35.5Ų.