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| Other Sizes |
| Targets |
1,4-Phenylenediboronic acid does not have a primary biological target as a test compound. However, boronic acids are known to reversibly inhibit serine proteases (e.g., trypsin, chymotrypsin) and the proteasome by forming a tetrahedral adduct with the active-site serine residue. When this diboronic acid is incorporated into larger molecules, it can target various enzymes. The compound is also used to prepare boron-containing drugs (e.g., boronic acid-based proteasome inhibitors) and as a chemical intermediate.
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| ln Vitro |
1,4-Phenylenediboronic acid is employed in Suzuki-Miyaura cross-coupling reactions, scholl cyclizations, and palladium-catalyzed sequential alkenylation and conjugate addition reactions. Additionally, it is employed in the production of derivatives of indolizide, including organic thin-film transistors, OLEDs, solution-processable coordination polymers, and F-fluorescence.
In vitro, the compound itself may inhibit serine proteases and the proteasome, although IC50 values are not well characterized. It may also be used in cell-free assays as a substrate for cross-coupling reactions, but not as a bioactive test article. For bortezomib (a boronic acid drug), IC50 for the 20S proteasome is 7 nM. This diboronic acid is likely much less potent due to the two boronic acids and lower affinity. No specific data. |
| ln Vivo |
No in vivo activity data are available for 1,4-phenylenediboronic acid. It is not administered to animals for therapeutic efficacy. However, polymeric materials or drug molecules synthesized using this building block may be tested in animal models of cancer or inflammation.
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| Enzyme Assay |
The compound is not used directly in enzyme binding assays. For cross-coupling applications, a typical Suzuki-Miyaura protocol: In a round-bottom flask, add 1,4-phenylenediboronic acid (1.0 eq, 5 mmol), an aryl halide (2.2 eq, 11 mmol), Pd(PPh3)4 (5 mol%), and K2CO3 (3 eq) in a mixture of dioxane/water (4:1, 30 mL). Degas with nitrogen for 15 minutes. Heat at 90degC for 12-16 hours under nitrogen. Cool, extract with ethyl acetate, wash with brine, dry over Na2SO4, and purify by column chromatography to obtain the bis(coupled) product. No biological assays.
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| Cell Assay |
No cell-based protocols are established for this compound. For downstream polyaromatic compounds synthesized using it, typical cell-based assays might include: cancer cell viability (HeLa, A549) measured by MTT after 48-72 hours exposure (0.1-100 uM). The building block itself is not added to cells.
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| Animal Protocol |
No animal studies have been conducted with 1,4-phenylenediboronic acid. For downstream compounds, in vivo efficacy studies might involve mice bearing xenografts treated with a bis(heteroaryl)benzene compound (10-50 mg/kg IP or PO). No data for the building block.
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| ADME/Pharmacokinetics |
No PK data are available for 1,4-phenylenediboronic acid. It is not a drug candidate. As a polar boronic acid (pKa ~8-9), it has low oral bioavailability. If administered, it may be rapidly oxidized to the corresponding phenol (1,4-dihydroxybenzene) or excreted unchanged. Boronic acids are generally metabolized via deboronation. No ADME studies reported. Solubility: low in water, soluble in DMSO, DMF, and alcohols.
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| Toxicity/Toxicokinetics |
Safety: May cause skin and eye irritation. Harmful if swallowed (estimated LD50 >2000 mg/kg). Boronic acids are generally low toxicity, but chronic exposure may affect bone development (interference with calcium and vitamin D). Not classified as carcinogen or mutagen. Use standard PPE: gloves, lab coat, safety goggles. Avoid inhalation of dust. Store at 2-8degC (or -20degC for long-term) in a tightly sealed container, protected from moisture (boronic acids may form anhydrides).
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| Additional Infomation |
1,4-Phenylenediboronic acid is not an approved drug and has no clinical trial history. It is a research chemical for organic synthesis, medicinal chemistry, and materials science. It is an essential building block for the synthesis of covalent organic frameworks (COFs), metal-organic frameworks (MOFs), conjugated polymers for organic electronics (OLEDs, solar cells), and porous materials. In medicinal chemistry, it is used to prepare symmetric bis(heteroaryl) compounds with potential activity as kinase inhibitors, G-quadruplex binders, and proteasome inhibitors. The compound is also a precursor to 1,4-dihydroxybenzene (hydroquinone) via oxidative deboronation. It is commercially available from chemical vendors for research use only.
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| Molecular Formula |
C6H8B2O4
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|---|---|
| Molecular Weight |
165.75
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| Exact Mass |
166.06
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| CAS # |
4612-26-4
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| Related CAS # |
676566-94-2
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| PubChem CID |
230478
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| Appearance |
White to off-white solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
420.1±55.0 °C at 760 mmHg
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| Melting Point |
>350 °C(lit.)
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| Flash Point |
207.9±31.5 °C
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| Vapour Pressure |
0.0±1.0 mmHg at 25°C
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| Index of Refraction |
1.555
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| LogP |
0.96
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
12
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| Complexity |
118
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1=C(C=CC(=C1)B(O)O)B(O)O
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| InChi Key |
BODYVHJTUHHINQ-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C6H8B2O4/c9-7(10)5-1-2-6(4-3-5)8(11)12/h1-4,9-12H
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| Chemical Name |
(4-boronophenyl)boronic acid
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO: 100 mg/mL (603.32 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (15.08 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (15.08 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (15.08 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 6.0332 mL | 30.1659 mL | 60.3318 mL | |
| 5 mM | 1.2066 mL | 6.0332 mL | 12.0664 mL | |
| 10 mM | 0.6033 mL | 3.0166 mL | 6.0332 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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