Chemical Identity and Structure

2-(4-Aminophenyl)-N,N-dimethylacetamide (SKU: N727116) is an aromatic amine acetamide derivative with the molecular formula C₁₀H₁₄N₂O and a molecular weight of approximately 178.23 g/mol. The compound features a para-aminophenyl ring bearing a methylene linker (–CH₂–) connecting to an N,N-dimethylacetamide group. This architecture provides two distinct reactive sites: the primary amine (–NH₂) on the aromatic ring, which can participate in diazotization, acylation, and condensation reactions, and the tertiary amide carbonyl, which offers moderate electrophilic character and hydrogen-bond-accepting capability.

The para substitution pattern on the phenyl ring ensures steric accessibility of the amine group, making this compound particularly attractive as a building block in multi-step synthetic sequences. The amide nitrogen is fully substituted with two methyl groups, precluding N–H reactivity at that site and directing reactivity selectively toward the aryl amine.

Laboratory Applications

The dual-functionality of 2-(4-Aminophenyl)-N,N-dimethylacetamide makes it valuable across several research domains:

• Pharmaceutical Intermediate: The free aryl amine serves as an attachment point for further derivatization, enabling construction of drug-like scaffolds such as sulfonamides, ureas, carbamates, and amides. Researchers engaged in medicinal chemistry campaigns frequently employ para-aminophenylacetamide motifs as pharmacophore components.
• Organic Synthesis: The compound can act as a coupling partner in palladium-catalyzed cross-coupling reactions after conversion of the amine to an appropriate leaving group (e.g., via Sandmeyer reactions). The N,N-dimethylacetamide moiety also provides a handle for studying amide bond geometry and conformational behavior in model systems.
• Materials Science Research: Amine-containing acetamide derivatives are explored as monomers or chain extenders in polyamide and polyurethane synthesis, as well as components in functional small-molecule systems.
• Biochemical Probes: Para-aminophenylacetamide cores appear in certain probe architectures designed to study enzyme active sites, particularly those recognizing aryl amine substrates such as acetyltransferases.

Researchers should verify specific application suitability through literature review and preliminary experiments, as performance may be context-dependent.

Handling, Safety, and Storage

Personal Protective Equipment (PPE): When working with 2-(4-Aminophenyl)-N,N-dimethylacetamide, wear appropriate PPE including chemical-resistant gloves (e.g., nitrile), a laboratory coat, and safety goggles. Work in a well-ventilated fume hood to minimize inhalation exposure to dust or vapors.

Hazard Considerations: As an aromatic amine compound, this material should be treated with appropriate caution. Aromatic amines as a class can pose health hazards; consult the Safety Data Sheet (SDS) for compound-specific GHS classification, hazard statements, and first-aid measures before use. Avoid contact with skin, eyes, and mucous membranes. Do not ingest.

Storage: Store in a tightly sealed container in a cool (typically 2–8 °C or room temperature as specified on the product label), dry, and well-ventilated location away from direct light, moisture, and incompatible materials such as strong oxidizers and strong acids. Always refer to the product-specific SDS and Certificate of Analysis (CoA) for authoritative storage instructions.

Disposal: Dispose of waste material in accordance with local, regional, and national regulations governing chemical waste. Do not dispose of down drains or into the environment.

Quality, Purity, and Procurement

Aladdin Scientific offers 2-(4-Aminophenyl)-N,N-dimethylacetamide under SKU N727116 as a research-grade reagent. Each lot is accompanied by a Certificate of Analysis (CoA) documenting purity, appearance, and other quality parameters. Researchers requiring high-purity material for sensitive assays should review the CoA for the specific lot prior to use.

Purity Verification: Common analytical techniques used to assess purity of such compounds include high-performance liquid chromatography (HPLC), nuclear magnetic resonance (NMR) spectroscopy, and mass spectrometry (MS). If your application requires a defined purity threshold, contact Aladdin Scientific's technical support team to discuss available grades and lot-specific data.

Ordering: The compound can be ordered directly through the Aladdin Scientific website or by contacting your regional sales representative. Bulk quantities and custom packaging may be available upon request. For procurement teams, reference SKU N727116 when placing orders to ensure correct product identification.