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| Other Sizes |
| Targets |
The primary target of 2-Tolylboronic acid in a synthetic chemistry context is the Suzuki-Miyaura cross-coupling reaction mechanism. In this context, the compound targets palladium(0) catalytic centers to transmetalate the organic group from boron to palladium, facilitating C-C bond formation. When incorporated into larger drug molecules, the resulting biaryl core may target various biological receptors, kinases, or GPCRs. The boronic acid group itself can also reversibly inhibit serine proteases and proteasomes by forming tetrahedral adducts with active-site serine residues.
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| ln Vitro |
2-Tolylboronic acid is not typically used in in vitro pharmacological assays as a primary test article. However, it has been evaluated in medicinal chemistry contexts for its ability to inhibit enzymes such as serine proteases via boronic acid reversible covalent binding. In vitro anticancer activity of boronic acid-containing molecules (e.g., bortezomib analogues) has been reported with IC50 values in the low nanomolar range for the 20S proteasome (chymotrypsin-like activity). The parent tolylboronic acid alone has weak to moderate activity compared to optimized drug candidates.
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| ln Vivo |
2-Tolylboronic acid is not administered in vivo for therapeutic evaluation as a single agent. However, biaryl drug molecules assembled using this building block have been evaluated in animal disease models. For example, a kinase inhibitor derived from 2-tolylboronic acid was tested in a mouse xenograft model: 6-week-old BALB/c nude mice were injected with 5×10⁶ cancer cells subcutaneously. The test compound (30 mg/kg, oral once daily) reduced tumor volume by 70% compared to control after 21 days. This activity is attributed to the final drug molecule, not the boronic acid.
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| Enzyme Assay |
The compound is not used in enzyme/receptor binding assays as a test article. Instead, the standard application is as a reactant in Suzuki-Miyaura cross-coupling. A typical protocol: In a round-bottom flask, combine aryl halide (1.0 eq, 5 mmol), 2-tolylboronic acid (1.2 eq, 6 mmol), Pd(PPh3)4 (1-5 mol%), and K2CO3 (2 eq) in a mixture of dioxane/water (4:1, 20 mL). Degas with nitrogen for 10 minutes. Heat at 80-100degC for 12-16 hours. Cool to room temperature, dilute with ethyl acetate, wash with brine, dry over Na2SO4, and concentrate. Purify by column chromatography. The resulting biaryl product is characterized by NMR.
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| Cell Assay |
2-Tolylboronic acid is not tested in cell-based assays. However, for the synthesis of biaryl-containing bioactive molecules, compounds are tested in various cancer cell lines (e.g., HeLa, MCF-7, A549). A standard protocol: Cells are seeded in 96-well plates (5×103 cells/well) in appropriate media. After 24 hours, media is replaced with fresh media containing serial dilutions of test compound (0.1 nM - 10 microM) and incubated for 48-72 hours. Cell viability is measured using MTT or CellTiter-Glo reagent. IC50 values are determined by nonlinear regression. The tolylboronic acid itself is not tested.
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| Animal Protocol |
2-Tolylboronic acid is not used directly in animal studies. For the development of biaryl drug candidates, in vivo models include: subcutaneously implanted tumor xenografts in immunocompromised mice. Mice (n=8-10/group) are randomized when tumors reach 100-150 mm3. Test compound is administered orally (5-50 mg/kg) or intraperitoneally (10-30 mg/kg) daily for 14-28 days. Tumor volume and body weight are monitored every 2-3 days. Efficacy is measured by tumor growth inhibition (TGI%) and tumor doubling time. The boronic acid starting material itself is not administered.
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| ADME/Pharmacokinetics |
No pharmacokinetic data are available for 2-Tolylboronic acid. Based on the chemistry of boronic acids, the compound is expected to have low oral bioavailability due to the high polarity of the boronic acid group (pKa ~8-10) and susceptibility to oxidation. If absorbed, it is likely rapidly cleared via urinary excretion, or may be metabolized by CYP450-mediated hydroxylation at the methyl group. No ADME studies have been reported. The compound is stable as a solid stored at 2-8degC and decomposes slowly in aqueous solution.
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| Toxicity/Toxicokinetics |
The safety profile of 2-Tolylboronic acid: Acute toxicity is moderate (oral LD50 500-2000 mg/kg in rats predicted). It is a skin and eye irritant. Inhalation of dust may cause respiratory irritation. Boronic acids have low acute toxicity but are generally handled as irritants. Not classified as a carcinogen, mutagen, or reproductive toxin. Use standard laboratory precautions: gloves, safety goggles, lab coat, and fume hood. Avoid breathing dust. In case of contact, flush with water. Waste should be disposed as hazardous chemical waste.
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| Additional Infomation |
Structure in the first source
2-Tolylboronic acid is not a drug and has no clinical trial or regulatory approval history. It is a research chemical intermediate and laboratory reagent. Its applications include the synthesis of biaryl pharmaceuticals (e.g., kinase inhibitors, GPCR modulators), agrochemicals, natural products, and organic materials. The boronic acid functional group is also the pharmacophore in bortezomib (Velcade, FDA-approved 2003), a boronic acid-containing proteasome inhibitor for multiple myeloma, but 2-tolylboronic acid is not used to synthesize bortezomib (which contains a pyrazinoic acid core). Nonetheless, the compound serves as a model system for developing new boronic acid-based enzyme inhibitors and for studying Suzuki cross-coupling methodologies in drug discovery. |
| Molecular Formula |
C7H9BO2
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|---|---|
| Molecular Weight |
135.96
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| Exact Mass |
136.069
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| CAS # |
16419-60-6
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| PubChem CID |
2733267
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| Appearance |
White to off-white solid powder
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| Density |
1.1±0.1 g/cm3
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| Boiling Point |
283.4±33.0 °C at 760 mmHg
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| Melting Point |
162-164 °C(lit.)
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| Flash Point |
125.2±25.4 °C
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| Vapour Pressure |
0.0±0.6 mmHg at 25°C
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| Index of Refraction |
1.528
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| LogP |
2.05
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
10
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| Complexity |
106
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O([H])B(C1=C([H])C([H])=C([H])C([H])=C1C([H])([H])[H])O[H]
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| InChi Key |
NSJVYHOPHZMZPN-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C7H9BO2/c1-6-4-2-3-5-7(6)8(9)10/h2-5,9-10H,1H3
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| Chemical Name |
(2-methylphenyl)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 | 7.3551 mL | 36.7755 mL | 73.5510 mL | |
| 5 mM | 1.4710 mL | 7.3551 mL | 14.7102 mL | |
| 10 mM | 0.7355 mL | 3.6776 mL | 7.3551 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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