| Size | Price | Stock | Qty |
|---|---|---|---|
| 250g |
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| Other Sizes |
| Targets |
4-Methoxyphenylboronic acid does not have a specific primary biological target, as it functions primarily as a chemical reagent and building block in organic synthesis and drug discovery rather than as a direct pharmacological agent. However, the compound has shown promise as an anticancer agent by inhibiting tubulin polymerization, which is crucial for cancer cell proliferation. In the context of bioconjugation, the compound interacts with biological molecules containing diol groups, such as sugars and glycoproteins, through the formation of reversible boronate esters. This interaction is the basis for its use in glucose sensors and targeted drug delivery systems. The compound also serves as an electrochemical redox probe for the selective detection of hydrogen peroxide (H2O2) in live cells, where it undergoes a selective analyte-triggered chemical transformation, releasing a free electrochemical reporter. In Suzuki-Miyaura cross-coupling reactions, it interacts with palladium catalysts to facilitate the transmetalation step.
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| ln Vitro |
In vitro, 4-methoxyphenylboronic acid is extensively used as a reagent in palladium-catalyzed reactions, including Suzuki-Miyaura cross-coupling, direct arylation, and highly effective synthesis using palladium-catalyzed arylation. One of its significant cellular effects is its role as an electrochemical redox probe for the selective detection of hydrogen peroxide in live cells. H2O2 plays an important role in human cell physiology, and its tracking and quantification in physiological systems are crucial for understanding cellular changes related to neoplastic conditions and redox homeostasis. The compound is also used in the synthesis of pharmaceuticals and agrochemicals through carbon-carbon bond formation. In material science, it is utilized in the development of polymeric materials with enhanced properties such as increased thermal stability and mechanical strength. The compound's ability to create boronate esters enables selective binding to diols in biological molecules, which is crucial for developing targeted drug delivery systems and biomolecular labeling.
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| ln Vivo |
In vivo studies are not typically performed with 4-methoxyphenylboronic acid, as it is primarily a synthetic reagent rather than a pharmacological agent. However, its derivatives and the compounds synthesized using it may be evaluated in animal models for various therapeutic applications. The compound's role in bioconjugation and sensor development suggests potential for in vivo applications in diagnostics and drug delivery, but specific in vivo studies on the parent compound are limited. The electrochemical detection of hydrogen peroxide using 4-methoxyphenylboronic acid has implications for understanding oxidative stress and redox homeostasis in living systems, which could be relevant for in vivo studies of neoplastic conditions. The compound's use in the synthesis of pharmaceuticals means that its derivatives may be tested in animal models for efficacy and safety, but the parent compound itself is not administered in vivo.
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| Enzyme Assay |
Cell-free assays involving 4-methoxyphenylboronic acid are primarily focused on its use as a chemical reagent. Standard Suzuki-Miyaura coupling protocols involve mixing the aryl halide (1 equivalent) with 4-methoxyphenylboronic acid (1.2 equivalents), a palladium catalyst (2-5 mol%), and a base (2 equivalents) in an appropriate solvent such as water or toluene at 80-100°C for 2-24 hours under an inert atmosphere. The reaction progress is monitored by TLC or HPLC, and the product is purified by column chromatography or recrystallization. For bioconjugation applications, the compound is incubated with diol-containing biomolecules in aqueous buffer at physiological pH to form boronate esters. In sensor development, the compound is used to detect glucose and other sugars through reversible covalent interactions. For electrochemical detection of hydrogen peroxide, the compound undergoes a selective analyte-triggered chemical transformation, releasing a free electrochemical reporter that can be measured.
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| Cell Assay |
Cellular assays using 4-methoxyphenylboronic acid are not standard, as the compound is primarily a chemical reagent. However, it has been used as an electrochemical redox probe for the selective detection of hydrogen peroxide in live cells. In these assays, cells are incubated with the compound, and the electrochemical signal is measured to quantify H2O2 production, providing a research tool for studying oxidative stress and redox homeostasis. The compound may also be used in cell-based assays to evaluate the activity of compounds synthesized using Suzuki coupling reactions. For example, drug candidates synthesized with 4-methoxyphenylboronic acid as a building block may be tested in cancer cell lines for antiproliferative activity. The compound itself is not typically used as a test article in cell-based experiments due to its role as a reagent rather than a bioactive compound.
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| Animal Protocol |
Animal studies are not typically conducted with 4-methoxyphenylboronic acid itself, as it is a chemical reagent rather than a pharmacological agent. The compound is primarily used in research focused on organic synthesis, bioconjugation, and sensor development. Its role in modifying drug structures can lead to improved efficacy and reduced side effects, making it a valuable tool in the development of new therapeutic agents, but the parent compound is not administered to animals. Any in vivo studies involving this compound would likely be focused on its derivatives or the final drug products synthesized using it. For example, drug candidates synthesized via Suzuki coupling with 4-methoxyphenylboronic acid may be evaluated in animal models for pharmacokinetics, efficacy, and toxicity. The compound's use in developing targeted drug delivery systems suggests potential for future in vivo applications, but specific studies on the parent compound are not documented.
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| ADME/Pharmacokinetics |
Pharmacokinetic data for 4-methoxyphenylboronic acid are not well characterized, as it is primarily a research reagent rather than a drug candidate. As a boronic acid with a molecular weight of 151.96 g/mol and an estimated pKa of approximately 8-9, it may undergo rapid clearance and metabolism in biological systems. The methoxy group enhances the electron density of the aromatic ring, influencing its reactivity and coupling efficiency. Boronic acids are known to form reversible covalent bonds with diols, which may affect their distribution and elimination. The compound is expected to have moderate membrane permeability due to its small size and lipophilic nature. However, comprehensive pharmacokinetic studies have not been performed, as the compound is not intended for therapeutic use. For research purposes, the compound is typically handled as a neat chemical and not administered to living organisms for pharmacokinetic profiling.
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| Toxicity/Toxicokinetics |
Toxicological data for 4-methoxyphenylboronic acid indicate potential for skin and eye irritation. Hazard classifications include Eye Irrit. 2, Skin Irrit. 2, and STOT SE 3 (respiratory system), indicating that the compound may cause irritation to the eyes, skin, and respiratory tract upon exposure. Appropriate safety precautions should be taken when handling the compound, including the use of personal protective equipment such as gloves, safety goggles, and respirators. The compound should be handled in a well-ventilated area, and contact with skin and eyes should be avoided. In case of exposure, affected areas should be rinsed thoroughly with water. The compound is not classified as a carcinogen or mutagen based on available data, but comprehensive toxicological evaluation has not been performed. As with all research chemicals, it should be handled with care and used only in accordance with safety guidelines.
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| Additional Infomation |
Structure in the first source
4-Methoxyphenylboronic acid is a research chemical, not an approved drug. It has no clinical trial or marketing approval status for therapeutic use. The compound is widely utilized in organic synthesis as a key reagent in Suzuki coupling reactions, enabling the formation of carbon-carbon bonds. It is particularly valuable in the synthesis of pharmaceuticals and agrochemicals. In bioconjugation, it is used to create boronate esters that can selectively bind to diols in biological molecules, which is crucial for developing targeted drug delivery systems and biomolecular labeling. The compound is also employed in the design of chemical sensors for detecting glucose and other sugars, benefiting diabetes management. In material science, it is utilized in the development of polymeric materials with enhanced properties. The compound can be synthesized by reacting 4-methoxyphenylmagnesium bromide with trimethyl borate, followed by hydrolysis. Industrial production typically involves palladium-catalyzed direct arylation or copper-mediated ligand-free aerobic fluoroalkylation. It should be stored at room temperature in a cool, dry place. |
| Molecular Formula |
C7H9BO3
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|---|---|
| Molecular Weight |
151.96
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| Exact Mass |
152.064
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| CAS # |
5720-07-0
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| PubChem CID |
201262
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| Appearance |
White to off-white solid powder
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
306.8±44.0 °C at 760 mmHg
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| Melting Point |
204-206 °C(lit.)
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| Flash Point |
139.3±28.4 °C
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| Vapour Pressure |
0.0±0.7 mmHg at 25°C
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| Index of Refraction |
1.524
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| LogP |
1.5
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
11
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| Complexity |
110
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O(C)C1C=CC(B(O)O)=CC=1
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| InChi Key |
VOAAEKKFGLPLLU-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C7H9BO3/c1-11-7-4-2-6(3-5-7)8(9)10/h2-5,9-10H,1H3
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| Chemical Name |
(4-methoxyphenyl)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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 6.5807 mL | 32.9034 mL | 65.8068 mL | |
| 5 mM | 1.3161 mL | 6.5807 mL | 13.1614 mL | |
| 10 mM | 0.6581 mL | 3.2903 mL | 6.5807 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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