3,5-Diformylphenylboronic acid

CAS Number 480424-62-2

Boronates, Carbaldehyde Monomers, Chemistry Building Blocks, COF Ligands, Materials, Porous Organic Frameworks

3,5-Diformylphenylboronic acid CAS 480424-62-2

Covalent Organic Frameworks (COFs) Diformylphenyl Ligand

A boronic acid bridging ligand linker for COFs in application of self-healing materials, drug delivery, cell capture and release

Overview
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3,5-Diformylphenylboronic acid (DFPBA), CAS number 480424-62-2, has two aldehydes and one boronic acid functional groups sitting at meta-position to each other on a benzene ring. Bearing both aldehyde and boronic acid, (3,5-Diformylphenyl)boronic acid can be used in highly efficient oxime click reaction, allowing the facile preparation of phenylboronic acid functional materials. Oxime click reaction is well known tool for rapid and high yield synthesis with great functional group tolerance, biocompatibility, and reversibility. The oxime click chemistry find applications in self-healing materials, bioconjugation, drug delivery and cell diagnostics.

Derived from (3,5-Diformylphenyl)boronic acid with double covalent bond of boroxine and an imine bond, delf-healing luminescent polymer PDMS-DPBA-5000 demonstrated high stretchability with an elongation of 4200% and stretch-induced fluorescence chromism from green to cyan. Polymer PDMS-DPBA-5000 showed great self-healing properties within 20 min at room temperature.

(3,5-Diformylphenyl)boronic acid has also been used in the dynamic covalent hydrogels for triggered cell capture and release. The formation of boronic ester between phenylboronic acid and carbohydrates on the cell surface enables efficient cell capture at pH 6.8 and cell detachment at PH 7.8 with a glucose concentration of 70 mM.

MOF and COF ligands

Aldehyde and Bpin ligand for cross-linked COF networks

Worldwide shipping

Quick and reliable shipping

High purity

>98% High purity

Duo functionality

Enabling post-functionalisation

General Information

CAS Number	480424-62-2
Chemical Formula	C₈H₇BO₄
Full Name	3,5-Diformylphenylboronic acid
Molecular Weight	177.95 g/mol
Synonyms	DFPBA
Classification / Family	Phenylboronic acid, COF ligands

Chemical Structure

Product Details

Purity	>98%
Melting Point	255 – 259 °C (Dec.)(lit.)
Appearance	White powder/crystals

MSDS Documentation

3,5-Diformylphenylboronic acid MSDS Sheet

Literature and Reviews

Dynamic Covalent Hydrogels for Triggered Cell Capture and Release, F. Karimi et al., Bioconjugate Chem., 28, 9, 2235–2240 (2017); DOI: 10.1021/acs.bioconjchem.7b00360.
Extremely rapid and versatile synthesis of high molecular weight step growth polymers via oxime click chemistry, J. Collins et al., Polym. Chem., 7, 2581-2588 (2016); DOI: 10.1039/C6PY00372A.
Highly stretchable and stretch-induced fluorescence chromism self-healing materials based on boroxine and dynamic imine bond, J. Wang et al., J. Mater. Chem. C, 10, 10895-10901 (2022); DOI: 10.1039/D2TC01886A.
Carboxylated Photoswitchable Diarylethenes for Biolabeling and Super-Resolution RESOLFT Microscopy, B. Roubinet et al., Angew. Chem., Int. Ed., 55 (49), 15429-15433 (2016); DOI: 10.1002/anie.201607940.
Benzimidazole–triazine based exciplex films as emitters and hosts to construct highly efficient OLEDs with a small efficiency roll-off, B. Liang et al., J. Mater. Chem. C, 8, 2700-2708 (2020); DOI: 10.1039/C9TC06212B.

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