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| Other Sizes |
| Targets |
4-(Boc-amino)benzeneboronic acid pinacol ester does not have a biological target as it is a synthetic organic reagent rather than a pharmacologically active compound. Its function is chemical rather than biological: it serves as a boronate ester that participates in palladium-catalyzed cross-coupling reactions. In the context of drug discovery, this compound is used to introduce a protected aniline moiety into biaryl drug candidates, where the eventual target of the final drug molecule may be a specific enzyme, receptor, or other protein. The compound itself is an intermediate and does not interact with biological macromolecules in a specific manner.
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| ln Vitro |
As a chemical reagent, 4-(Boc-amino)benzeneboronic acid pinacol ester exhibits no intrinsic pharmacological activity in vitro. Its utility is demonstrated in Suzuki-Miyaura coupling reactions, where it achieves 46% isolated yields for biaryl cores under optimized conditions. The pinacol ester provides a hydrolytic half-life of >2 hours in neutral water, facilitating aqueous-scale-up reactions. In cell-based assays, the compound itself is not tested for biological activity. Instead, the biaryl products synthesized from this reagent are evaluated for their pharmacological properties. The compound is used in high-throughput experimentation and parallel synthesis due to its crystalline nature and accurate dispensability.
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| ln Vivo |
No in vivo biological activity is attributed to 4-(Boc-amino)benzeneboronic acid pinacol ester, as it is a chemical intermediate not intended for therapeutic applications. The compound is used exclusively in organic synthesis and medicinal chemistry research to construct biaryl frameworks that may ultimately become drug candidates. Any in vivo effects would be associated with the final pharmaceutical products synthesized from this reagent, not with the reagent itself. The compound is not administered to animals in pharmacological studies and has no known physiological effects. Its role is strictly chemical—enabling the construction of complex molecular architectures.
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| Enzyme Assay |
In vitro enzyme/receptor binding assays are not applicable to 4-(Boc-amino)benzeneboronic acid pinacol ester as it is not a biologically active compound. Standard characterization protocols for this reagent include nuclear magnetic resonance (¹H NMR, ¹³C NMR, ¹¹B NMR) and mass spectrometry to confirm structure and purity. Melting point determination (167-170°C) is used for quality control. For Suzuki-Miyaura coupling reactions, typical conditions involve dissolving the boronic ester with an aryl halide, a palladium catalyst (e.g., Pd(PPh₃)₄ or Pd(dppf)Cl₂), and a base (e.g., K₂CO₃ or Cs₂CO₃) in a solvent such as dioxane or THF, and heating at 80-100°C for several hours.
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| Cell Assay |
Cell-based experiments are not performed with 4-(Boc-amino)benzeneboronic acid pinacol ester itself, as it is a chemical reagent and not a test compound for biological activity. If the compound is used to synthesize biaryl drug candidates, those products may be tested in cell culture using standard protocols. Typically, the final compounds are dissolved in DMSO and diluted in cell culture media to achieve desired concentrations. Cells are incubated with the test compounds for 24-72 hours, and cell viability is measured using MTT, resazurin, or ATP-luminescence assays. The boronic ester reagent itself is not evaluated in cellular systems.
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| Animal Protocol |
In vivo animal studies are not conducted with 4-(Boc-amino)benzeneboronic acid pinacol ester, as it is a research reagent for organic synthesis. When the compound is used to synthesize drug candidates, those final products undergo standard preclinical evaluation. Typical protocols for drug candidates include oral gavage or intravenous injection in rodents, collection of blood samples at multiple time points for pharmacokinetic analysis, tissue harvesting for biodistribution studies, and histopathological examination. These studies evaluate the safety and efficacy of the final drug molecules, not the synthetic intermediate used in their preparation.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of 4-(Boc-amino)benzeneboronic acid pinacol ester are not characterized as it is not a drug substance. Based on its physicochemical properties (molecular weight 319.2, logP approximately 3.5, crystalline solid), the compound is expected to be poorly water-soluble and lipophilic. If absorbed, it would likely undergo extensive metabolism, including deprotection of the Boc group and oxidative deboronation. The compound is not intended for human exposure and has not been evaluated in formal pharmacokinetic studies. For drug candidates synthesized using this reagent, pharmacokinetic properties are determined as part of the drug development process.
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| Toxicity/Toxicokinetics |
Toxicological data for 4-(Boc-amino)benzeneboronic acid pinacol ester are limited as it is a research reagent. Standard laboratory safety precautions should be followed when handling this compound, including the use of gloves, safety glasses, and working in a fume hood. The compound contains a boronic ester moiety, which may hydrolyze to release boric acid derivatives. No acute toxicity data are available. The compound is not intended for drug, household, or other uses. It should be stored in a cool, dry place away from moisture and strong oxidizing agents.
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| Additional Infomation |
4-(Boc-amino)benzeneboronic acid pinacol ester is a valuable building block in medicinal chemistry for the synthesis of biaryl-containing pharmaceuticals. The Boc protecting group enables selective deprotection after coupling to reveal the free aniline, which can be further functionalized to amides, ureas, or other derivatives. The pinacol ester provides stability during storage and reaction, reducing protodeboronation side reactions. This compound is commonly used in drug discovery campaigns targeting kinases, GPCRs, and other therapeutic targets. It is available in standard pack sizes of 1 g and 5 g. The compound has not undergone clinical trials and is not approved as a pharmaceutical. Its mechanism of action is chemical—facilitating carbon-carbon bond formation in the synthesis of biologically active molecules.
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| Molecular Formula |
C17H26BNO4
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|---|---|
| Molecular Weight |
319.20
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| Exact Mass |
319.195
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| CAS # |
330793-01-6
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| PubChem CID |
2734617
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| Appearance |
Off-white to light brown solid powder
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| Density |
1.1±0.1 g/cm3
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| Boiling Point |
381.1±25.0 °C at 760 mmHg
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| Melting Point |
167-170 °C(lit.)
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| Flash Point |
184.3±23.2 °C
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| Vapour Pressure |
0.0±0.9 mmHg at 25°C
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| Index of Refraction |
1.504
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| LogP |
3.405
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
23
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| Complexity |
420
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CC(C)(C)OC(=O)NC1=CC=C(C=C1)B1OC(C)(C)C(C)(C)O1
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| InChi Key |
HSJNIOYPTSKQBD-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C17H26BNO4/c1-15(2,3)21-14(20)19-13-10-8-12(9-11-13)18-22-16(4,5)17(6,7)23-18/h8-11H,1-7H3,(H,19,20)
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| Chemical Name |
tert-butyl N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate
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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 | 3.1328 mL | 15.6642 mL | 31.3283 mL | |
| 5 mM | 0.6266 mL | 3.1328 mL | 6.2657 mL | |
| 10 mM | 0.3133 mL | 1.5664 mL | 3.1328 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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