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| Targets |
2-Cyanophenylboronic acid is a synthetic intermediate and building block used in medicinal chemistry. As a building block, it does not have specific biological receptors as its primary targets. The boronic acid functionality allows for reversible covalent bonding with diols and other nucleophiles, making it valuable for Suzuki-Miyaura cross-coupling reactions. The nitrile group can be hydrolyzed to carboxylic acid or reduced to amine. The compound is used in the synthesis of TAK1 inhibitors and VCP inhibitors. Its primary applications are as a synthetic intermediate for drug discovery.
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| ln Vitro |
In vitro, 2-cyanophenylboronic acid is used as a biochemical reagent and organic compound for biomedical research. It is used in the synthesis of pyridine inhibitors of TAK1. It participates in the discovery and synthesis of 1,2,4-triazoles as novel allosteric VCP inhibitors. It is employed in a rhodium-catalyzed [3+2] annulation with alkynes. Cellular assays are typically performed on the final compounds synthesized from this building block. The compound's boronic acid and nitrile functionalities allow for various chemical transformations, making it valuable for drug discovery.
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| ln Vivo |
In vivo data for 2-cyanophenylboronic acid is limited, as it is primarily a research reagent and synthetic intermediate. The compound is classified for research use only and is not intended for human or veterinary therapeutic applications. However, TAK1 inhibitors and VCP inhibitors synthesized using this building block have been investigated for their therapeutic potential. The compound's primary value lies in its use as a synthetic intermediate for preparing various bioactive compounds. Specific in vivo data for the parent compound is not available in the public literature.
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| Enzyme Assay |
In vitro enzyme assays for 2-cyanophenylboronic acid are not typically performed, as it is primarily a synthetic intermediate. The compound is used as a building block in the synthesis of TAK1 inhibitors and VCP inhibitors. A typical assay involves using the compound in chemical reactions, including Suzuki-Miyaura cross-coupling and rhodium-catalyzed annulation. The compound is dissolved in organic solvents such as DMSO or THF. The resulting products can be evaluated for biological activity. Kinase inhibition assays with purified TAK1 or other targets can be performed on the final synthesized compounds. IC₅₀ values are calculated from dose-response curves.
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| Cell Assay |
Cellular assays for 2-cyanophenylboronic acid derivatives typically evaluate TAK1 or VCP inhibitory activity. A standard protocol involves culturing appropriate cell lines in growth medium at 37°C with 5% CO₂. Cells are treated with synthesized compounds at varying concentrations for 24-72 hours. Cell viability is assessed using MTT or similar assays. Target inhibition is evaluated by measuring phosphorylation of downstream targets or protein levels by Western blot or ELISA. IC₅₀ values are calculated from dose-response curves.
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| Animal Protocol |
In vivo animal studies for 2-cyanophenylboronic acid are not standard, as it is a synthetic intermediate rather than a therapeutic candidate. The compound is classified for research use only and is not intended for human or veterinary applications. Any animal studies would typically be conducted on the final TAK1 or VCP inhibitors synthesized using this building block. These studies would evaluate efficacy, pharmacokinetics, and safety in appropriate animal models. The compound's primary value lies in its use as a synthetic intermediate.
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| ADME/Pharmacokinetics |
Pharmacokinetic data for 2-cyanophenylboronic acid is limited, as it is primarily a research reagent. The compound has a molecular weight of 146.94 g/mol and a molecular formula of C₇H₆BNO₂. It is a solid at room temperature. As a boronic acid, it may undergo oxidation and hydrolysis. The nitrile group may be metabolized to carboxylic acid. Specific ADME data is not available. The compound is stored in a dry, cool place.
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| Toxicity/Toxicokinetics |
2-Cyanophenylboronic acid is classified for research use only and is not intended for human or veterinary applications. Standard safety precautions include handling with appropriate personal protective equipment (gloves, lab coat, safety goggles) in a well-ventilated area. The compound should be stored in a dry, cool place away from incompatible materials. Acute toxicity data is not readily available in the public literature. As with all research chemicals, appropriate laboratory safety practices should be followed. No specific LD₅₀ values or detailed toxicological profiles are available in the public domain.
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| Additional Infomation |
2-Cyanophenylboronic acid (2-Cyanobenzeneboronic acid, CAS 138642-62-3) is a biochemical reagent with the molecular formula C₇H₆BNO₂. It is used as a building block in the synthesis of TAK1 inhibitors, VCP inhibitors, and in rhodium-catalyzed annulation reactions. The compound is classified as a research-use-only compound not intended for diagnostic or therapeutic purposes. It is available from multiple commercial suppliers in various pack sizes. No clinical trials or approved drug status exist for this compound as it is not a therapeutic agent.
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| Molecular Formula |
C7H6BNO2
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|---|---|
| Molecular Weight |
146.94
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| Exact Mass |
147.049
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| CAS # |
138642-62-3
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| PubChem CID |
2734610
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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 |
376.4±44.0 °C at 760 mmHg
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| Melting Point |
240 °C (dec.)(lit.)
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| Flash Point |
181.4±28.4 °C
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| Vapour Pressure |
0.0±0.9 mmHg at 25°C
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| Index of Refraction |
1.560
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| LogP |
1.03
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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 |
1
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| Heavy Atom Count |
11
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| Complexity |
175
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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#N)O[H]
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| InChi Key |
NPLZNDDFVCGRAG-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C7H6BNO2/c9-5-6-3-1-2-4-7(6)8(10)11/h1-4,10-11H
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| Chemical Name |
(2-cyanophenyl)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 | 6.8055 mL | 34.0275 mL | 68.0550 mL | |
| 5 mM | 1.3611 mL | 6.8055 mL | 13.6110 mL | |
| 10 mM | 0.6805 mL | 3.4027 mL | 6.8055 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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