N-(2-Benzylphenyl)pivalamide: Properties, Uses & FAQs

N-(2-Benzylphenyl)pivalamide is a well-defined aromatic amide building block widely employed in directed C–H bond functionalization research, serving as a substrate or reference standard in transition-metal-catalyzed coupling and C–H activation studies.

Chemical Name

N-(2-Benzylphenyl)pivalamide

SKU / Catalog Number

N698894 (Aladdin Scientific)

Molecular Formula

C₁₈H₂₁NO

Molecular Weight

267.37 g/mol

Functional Class

Aromatic amide; directing-group substrate for C–H functionalization

Recommended Storage

Cool, dry place; away from light and moisture (verify CoA for exact conditions)

What Is N-(2-Benzylphenyl)pivalamide and Why Is It Used in Research?

N-(2-Benzylphenyl)pivalamide is an aromatic amide consisting of a 2-benzylphenyl ring system acylated with a pivaloyl (trimethylacetyl) group. The compound carries two key structural features that make it valuable in synthetic chemistry: (1) a pivalamide directing group, which coordinates strongly to transition metals (e.g., Pd, Ni, Rh) and positions the metal centre in proximity to specific C–H bonds; and (2) a benzylic methylene tether at the ortho position, which influences the conformational landscape and selectivity of metalacycle formation.

Researchers use this compound primarily as a model substrate to develop and benchmark directed C–H activation/functionalization protocols, and as a synthetic intermediate in the construction of more complex nitrogen-containing frameworks. Its well-defined structure allows straightforward characterisation by NMR, HRMS, and IR, making it convenient for mechanistic and kinetic studies.

Physicochemical Properties and Handling Guidelines

Physical state: N-(2-Benzylphenyl)pivalamide is expected to be a white to off-white solid at room temperature based on its molecular structure and weight (MW 267.37 g/mol, molecular formula C₁₈H₂₁NO). Exact melting point and detailed physicochemical data should be confirmed from the product Certificate of Analysis (CoA) available on the Aladdin website.

Solubility: The compound is anticipated to dissolve in common organic solvents such as dichloromethane, ethyl acetate, THF, and DMSO. Solubility in water is expected to be low owing to the lipophilic benzyl and tert-butyl substituents. Always perform a small-scale solubility test before large-scale use.

Stability and storage: Store in a tightly sealed container in a cool, dry location away from light and moisture. Prolonged exposure to heat or humidity may cause degradation. Refer to the CoA and Safety Data Sheet (SDS) supplied with each lot for authoritative storage temperature recommendations.

Safety: As with all fine chemical reagents, handle with appropriate PPE (lab coat, nitrile gloves, safety glasses). Consult the SDS for hazard classification, first-aid measures, and disposal requirements before use.

Purity, Quality Specifications, and Regulatory Compliance

Aladdin Scientific supplies N-(2-Benzylphenyl)pivalamide (SKU: N698894) as a research-grade reagent. Purity is verified by HPLC or GC analysis and is documented on the lot-specific Certificate of Analysis (CoA). Customers should download or request the CoA for their specific lot to confirm purity grade, appearance, and any additional analytical data.

For applications requiring higher purity — such as quantitative reference standards, kinetic studies, or pharmaceutical pre-screening — please contact Aladdin's technical support team to discuss available grades and custom purification options.

This product is intended for research use only and is not approved for human therapeutic or diagnostic use. Export of this reagent may be subject to national regulations; buyers are responsible for compliance with applicable import/export controls.

Ordering, Shipping, and Storage Upon Receipt

How to order: N-(2-Benzylphenyl)pivalamide (SKU N698894) can be ordered directly through the Aladdin Scientific website. Add the product to your cart, select the required quantity, and proceed through the standard checkout. Purchase orders from institutions are accepted; contact our sales team for quotation and volume pricing.

Shipping: The compound is shipped as a solid at ambient temperature under standard conditions. For international orders, estimated delivery times and applicable customs documentation will be communicated at checkout or by the Aladdin logistics team. Aladdin follows all applicable carrier regulations for chemical shipments.

Upon receipt: Inspect the package for damage before opening. Verify the lot number against your CoA. Transfer to appropriate storage conditions immediately. If any discrepancy in appearance, quantity, or documentation is observed, contact Aladdin customer service promptly to initiate a returns or replacement process.

Frequently asked questions

What is the catalog number for N-(2-Benzylphenyl)pivalamide at Aladdin Scientific?

The catalog (SKU) number for N-(2-Benzylphenyl)pivalamide at Aladdin Scientific is N698894. You can search this SKU directly on the Aladdin website to access product details, pricing, availability, and the lot-specific Certificate of Analysis.

What is N-(2-Benzylphenyl)pivalamide used for in organic chemistry research?

N-(2-Benzylphenyl)pivalamide is primarily used as a model substrate and synthetic building block in directed C–H bond functionalization research. The pivalamide group acts as a directing group that coordinates to transition-metal catalysts (such as palladium, rhodium, or nickel complexes), enabling selective C–H activation and subsequent functionalization. It may also serve as an intermediate in multi-step syntheses targeting heterocyclic or biaryl targets.

What solvents can be used to dissolve N-(2-Benzylphenyl)pivalamide?

Based on its lipophilic structure (aromatic rings and a tert-butyl group), N-(2-Benzylphenyl)pivalamide is expected to be soluble in polar aprotic solvents such as DMSO and DMF, as well as common organic solvents including dichloromethane, ethyl acetate, and THF. Aqueous solubility is expected to be very low. We recommend performing a small-scale solubility test and consulting the CoA for verified data.

How should N-(2-Benzylphenyl)pivalamide be stored to maintain stability?

N-(2-Benzylphenyl)pivalamide should be stored in a tightly sealed container in a cool, dry place, protected from light and moisture. Refer to the lot-specific Safety Data Sheet (SDS) and Certificate of Analysis (CoA) for the exact recommended storage temperature and any special handling precautions confirmed by Aladdin's quality control team.

What purity grade is available, and how can I verify it?

Aladdin supplies N-(2-Benzylphenyl)pivalamide as a research-grade reagent with purity verified by HPLC or GC analysis. The exact purity figure for your lot is documented on the Certificate of Analysis (CoA), which can be downloaded from the product page on the Aladdin website using your lot number. For higher-purity or custom grades, please contact Aladdin's technical support.

Can I return or exchange N-(2-Benzylphenyl)pivalamide if there is a quality issue?

Yes. Aladdin Scientific has a returns and refunds policy covering quality discrepancies. If you receive a product that does not meet the specifications stated on the CoA, or if packaging is damaged upon arrival, contact Aladdin customer service promptly with your order number, lot number, and a description of the issue. The team will guide you through the returns or replacement process in accordance with Aladdin's standard policy.

References

1. Aladdin Scientific product page: N-(2-Benzylphenyl)pivalamide, SKU N698894. Aladdin Scientific.
2. Daugulis O, Do H-Q, Shabashov D. Palladium- and copper-catalyzed arylation of carbon-hydrogen bonds. Accounts of Chemical Research. 2009;42(8):1074-1086. [General reference for pivalamide-directed C-H activation; specific applicability to this substrate needs verification.] doi:10.1021/ar9000672

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.