(4-(Benzyl(methyl)carbamoyl)phenyl)boronic Acid: Properties & Uses
(4-(Benzyl(methyl)carbamoyl)phenyl)boronic Acid: Properties & Uses
(4-(Benzyl(methyl)carbamoyl)phenyl)boronic acid is a functionalized arylboronic acid building block bearing a tertiary amide substituent that makes it a versatile reagent for palladium-catalyzed cross-coupling reactions and medicinal chemistry synthesis.
- Product Name
- (4-(Benzyl(methyl)carbamoyl)phenyl)boronic acid
- SKU
- C732035
- Molecular Formula
- C15H16BNO3
- Core Functional Groups
- Boronic acid (-B(OH)2) and tertiary amide (N-benzyl-N-methylamide)
- Primary Application
- Suzuki–Miyaura cross-coupling and medicinal chemistry building block
- Supplier
- Aladdin Scientific (C732035)
Chemical Structure and Key Functional Groups
(4-(Benzyl(methyl)carbamoyl)phenyl)boronic acid features a para-substituted benzene ring carrying two distinct functional groups: a boronic acid group (-B(OH)2) at one position and a tertiary amide group — specifically an N-benzyl-N-methylamide — at the para position. The boronic acid moiety is the reactive handle exploited in cross-coupling, condensation with diols, and covalent-biology applications, while the tertiary amide confers conformational rigidity, influences electronic density on the aryl ring, and provides a pharmacophore frequently encountered in drug candidates. The combination of these two functional groups in a single, stable, crystalline solid makes this compound a dual-purpose building block valued in synthetic and medicinal chemistry workflows.
Synthesis and Reactivity in Cross-Coupling Chemistry
Arylboronic acids such as (4-(Benzyl(methyl)carbamoyl)phenyl)boronic acid are canonical coupling partners in the Suzuki–Miyaura reaction, one of the most widely used C–C bond-forming methods in modern organic synthesis. Under palladium catalysis and mild base conditions, the boronic acid undergoes transmetalation with a palladium(II) species generated from an aryl or vinyl halide (or pseudohalide) electrophile, followed by reductive elimination to yield a biaryl or styrene-type product bearing the intact amide substituent. The electron-withdrawing nature of the amide group moderately deactivates the aryl ring toward electrophilic processes but does not significantly impede the boronic acid's performance in cross-coupling. This compound may also participate in Chan–Lam amination and related oxidative coupling reactions. Researchers should note that, like all arylboronic acids, this compound is susceptible to protodeboronation under strongly acidic or basic aqueous conditions and to oxidative degradation; storage under inert atmosphere at low temperature is recommended to maintain purity.
Applications in Medicinal Chemistry and Drug Discovery
The tertiary amide pharmacophore present in (4-(Benzyl(methyl)carbamoyl)phenyl)boronic acid is a recurring motif in approved drugs and clinical candidates, making this boronic acid a high-value fragment for library synthesis via Suzuki coupling or other transformations. Fragment-based drug discovery (FBDD) and high-throughput parallel synthesis programs use arylboronic acid building blocks to rapidly assemble biaryl scaffolds for structure–activity relationship (SAR) studies. Additionally, boronic acids themselves are recognized pharmacophores: they form reversible covalent bonds with serine and threonine residues in enzyme active sites, as exemplified by the proteasome inhibitor bortezomib. While (4-(Benzyl(methyl)carbamoyl)phenyl)boronic acid has not been reported as a drug itself, its structural features position it as a useful intermediate for probing enzyme active sites and for the synthesis of peptidomimetic and non-peptidic protease inhibitor candidates. Procurement teams should confirm purity specifications and certificate of analysis (CoA) details directly with Aladdin Scientific for GLP or regulated research use.
Handling, Storage, and Laboratory Safety
As with other arylboronic acids, (4-(Benzyl(methyl)carbamoyl)phenyl)boronic acid should be handled following standard laboratory safety precautions. Personnel should wear appropriate personal protective equipment (PPE) including gloves, safety glasses, and a laboratory coat. Avoid inhalation of dust or aerosols. The compound should be stored in a tightly sealed container, preferably under an inert atmosphere (nitrogen or argon), at 2–8 °C or as specified on the product label, protected from moisture and light to prevent hydrolysis and oxidative degradation. Boronic acids can form anhydrides (boroxines) upon prolonged exposure to heat or vacuum drying; this should be accounted for when preparing stock solutions or weighing quantities for reaction. Consult the Safety Data Sheet (SDS) provided by Aladdin Scientific (SKU C732035) for full hazard classification, first-aid measures, and disposal guidance before use.
Frequently asked questions
What is (4-(Benzyl(methyl)carbamoyl)phenyl)boronic acid primarily used for in research?
It is primarily used as a building block in palladium-catalyzed Suzuki–Miyaura cross-coupling reactions to construct biaryl frameworks, and in medicinal chemistry programs for synthesizing compound libraries that incorporate both an arylboronic acid handle and a tertiary amide pharmacophore.
How should (4-(Benzyl(methyl)carbamoyl)phenyl)boronic acid be stored to maintain stability?
The compound should be stored in a tightly sealed container under an inert atmosphere (nitrogen or argon) at low temperature (2–8 °C or as indicated on the product label), away from moisture and light. These conditions minimize hydrolysis of the boronic acid group and prevent oxidative degradation.
Can (4-(Benzyl(methyl)carbamoyl)phenyl)boronic acid be used in Chan–Lam coupling reactions?
Arylboronic acids are established substrates for Chan–Lam coupling, which uses a copper catalyst to form C–N, C–O, or C–S bonds. (4-(Benzyl(methyl)carbamoyl)phenyl)boronic acid is structurally suitable for such reactions; however, researchers should optimize reaction conditions for this specific substrate and consult recent literature for guidance.
What is the SKU for ordering (4-(Benzyl(methyl)carbamoyl)phenyl)boronic acid from Aladdin Scientific?
The SKU is C732035. Researchers and procurement staff can reference this code when placing orders or requesting a quotation from Aladdin Scientific.
References
- Miyaura, N.; Suzuki, A. Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds. Chemical Reviews 1995, 95 (7), 2457–2483. doi:10.1021/cr00039a007
- Hall, D. G. (Ed.) Boronic Acids: Preparation and Applications in Organic Synthesis, Medicine and Materials, 2nd ed.; Wiley-VCH: Weinheim, 2011.
- Lam, P. Y. S.; Clark, C. G.; Saubern, S.; Adams, J.; Winters, M. P.; Chan, D. M. T.; Combs, A. New aryl/heteroaryl C–N bond cross-coupling reactions via arylboronic acid/cupric acetate arylation. Tetrahedron Letters 1998, 39 (19), 2941–2944. doi:10.1016/S0040-4039(98)00419-0
- Adams, J.; Behnke, M.; Chen, S.; et al. Potent and selective inhibitors of the proteasome: dipeptidyl boronic acids. Bioorganic & Medicinal Chemistry Letters 1998, 8 (4), 333–338. doi:10.1016/S0960-894X(98)00029-8
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