| Size | Price | |
|---|---|---|
| Other Sizes |
| Targets |
3-Hydroxyphenylboronic acid pinacol ester does not have a defined primary drug target as it is a chemical reagent and synthetic building block rather than a therapeutic agent. However, boronic acid-containing compounds have been extensively studied as proteasome inhibitors (e.g., bortezomib) and as inhibitors of serine proteases, β-lactamases, and other enzymes containing nucleophilic active-site residues. The boronic acid moiety can form reversible covalent bonds with hydroxyl and amino groups in biological molecules. The phenolic group can participate in hydrogen bonding and other interactions. Compounds synthesized using this reagent as a building block may target various enzymes.
|
|---|---|
| ln Vitro |
As a synthetic reagent, 3-Hydroxyphenylboronic acid pinacol ester is not typically evaluated for direct in vitro biological activity against specific molecular targets. Boronic acids in general are known to interact with diols and carbohydrates, and some derivatives exhibit enzyme inhibitory activity. However, the parent compound is used primarily as a chemical tool rather than a bioactive molecule. Its activity in biological assays would depend on the specific context and concentration, and any observed effects are generally considered incidental.
|
| ln Vivo |
In vivo activity data for 3-Hydroxyphenylboronic acid pinacol ester itself is not available, as the compound is not intended for therapeutic use. Drug candidates synthesized using this boronic ester as a building block may be evaluated in animal models for various indications, but the biological activity is attributed to the final drug molecule rather than the boronic ester reagent. The compound's primary applications remain in chemical synthesis and medicinal chemistry research.
|
| Enzyme Assay |
Cell-free biochemical assays involving 3-Hydroxyphenylboronic acid pinacol ester typically focus on its use as a reagent in Suzuki-Miyaura coupling reactions. A standard protocol involves mixing the boronic ester with an aryl halide, a palladium catalyst (e.g., Pd(PPh₃)₄ or PdCl₂(dppf)), and a base (e.g., K₂CO₃ or Cs₂CO₃) in an appropriate solvent such as THF, dioxane, or DMF/water mixture. The reaction is typically heated to 80-100°C for several hours under inert atmosphere, and progress is monitored by TLC or GC-MS. The product is isolated by extraction and purified by column chromatography. The pinacol ester is typically deprotected to the free boronic acid under acidic conditions before biological testing.
|
| Cell Assay |
Cell-based assays are not typically performed with 3-Hydroxyphenylboronic acid pinacol ester as the compound is a chemical reagent. For drug molecules synthesized using this reagent, standard cell-based protocols would apply depending on the target indication. For example, cancer cell lines may be treated with the synthesized compound at concentrations ranging from 0.1-100 μM for 24-72 hours, and cell viability assessed by MTT or CellTiter-Glo assays. The boronic ester reagent itself may be used as a control to confirm that observed activity is due to the final compound structure.
|
| Animal Protocol |
In vivo studies are not typically conducted with 3-Hydroxyphenylboronic acid pinacol ester itself. For drug candidates synthesized using this reagent, standard in vivo efficacy studies involve rodent models of the target disease. A typical protocol includes oral or intravenous administration of the test compound at various doses, with monitoring of disease progression through appropriate endpoints. The boronic acid moiety in drug molecules can contribute to target engagement through reversible covalent binding to active-site residues. The pinacol ester is typically hydrolyzed to the active boronic acid form in vivo.
|
| ADME/Pharmacokinetics |
As a chemical reagent rather than a drug, comprehensive pharmacokinetic data for 3-Hydroxyphenylboronic acid pinacol ester is not available. The compound's molecular weight is 220.07 g/mol. The pinacol ester protects the boronic acid, enhancing stability and lipophilicity. For drug molecules containing boronic acid moieties, the pinacol ester is typically a prodrug that is hydrolyzed to the active boronic acid in vivo. PK parameters depend on the overall molecular structure and are determined empirically.
|
| Toxicity/Toxicokinetics |
Toxicological data specific to 3-Hydroxyphenylboronic acid pinacol ester is limited. As with all boronic esters and chemical reagents, standard laboratory safety precautions should be observed when handling this compound. The compound may cause irritation upon skin or eye contact, and inhalation of dust should be avoided. For drug candidates synthesized using this reagent, comprehensive toxicological evaluation is required as part of the drug development process.
|
| Additional Infomation |
3-Hydroxyphenylboronic acid pinacol ester is a research chemical and synthetic reagent rather than an approved pharmaceutical agent. No clinical trials or regulatory approvals exist for this compound itself. It is commercially available from various chemical suppliers for research purposes only. The compound's primary value lies in its utility as a building block in Suzuki-Miyaura cross-coupling reactions for the synthesis of biaryls and other complex organic molecules. The phenolic hydroxyl group provides a handle for further functionalization, making this compound a versatile intermediate for pharmaceutical synthesis and medicinal chemistry research.
|
| Molecular Formula |
C12H17BO3
|
|---|---|
| Molecular Weight |
220.07
|
| Exact Mass |
220.127
|
| CAS # |
214360-76-6
|
| PubChem CID |
2734623
|
| Appearance |
White to off-white solid powder
|
| Density |
1.1±0.1 g/cm3
|
| Boiling Point |
343.6±25.0 °C at 760 mmHg
|
| Melting Point |
94-98 °C(lit.)
|
| Flash Point |
161.6±23.2 °C
|
| Vapour Pressure |
0.0±0.8 mmHg at 25°C
|
| Index of Refraction |
1.515
|
| LogP |
1.691
|
| Hydrogen Bond Donor Count |
1
|
| Hydrogen Bond Acceptor Count |
3
|
| Rotatable Bond Count |
1
|
| Heavy Atom Count |
16
|
| Complexity |
249
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
O1B(C2C([H])=C([H])C([H])=C(C=2[H])O[H])OC(C([H])([H])[H])(C([H])([H])[H])C1(C([H])([H])[H])C([H])([H])[H]
|
| InChi Key |
MUKIFYQKIZOYKT-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C12H17BO3/c1-11(2)12(3,4)16-13(15-11)9-6-5-7-10(14)8-9/h5-8,14H,1-4H3
|
| Chemical Name |
3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol
|
| HS Tariff Code |
2934.99.9001
|
| 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)
|
| 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
|
|---|---|
| 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 | 4.5440 mL | 22.7200 mL | 45.4401 mL | |
| 5 mM | 0.9088 mL | 4.5440 mL | 9.0880 mL | |
| 10 mM | 0.4544 mL | 2.2720 mL | 4.5440 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.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
