Overview
4-Aminoacetophenone is an aromatic organic compound belonging to the acetophenone family. As a bifunctional molecule containing both amino and ketone groups, it serves as a versatile building block in organic synthesis. Industrially produced through Friedel-Crafts acylation followed by nitration and reduction, this compound has been commercially significant since the mid-20th century. The chemical finds extensive use in specialty chemical manufacturing, particularly for producing heterocyclic compounds. Its molecular structure allows for diverse chemical transformations, making it valuable for creating complex molecules in pharmaceutical research and fine chemical production.
Physical and Chemical Properties
This crystalline solid typically appears as yellow needles or powder with a characteristic mild aromatic odor. It demonstrates moderate thermal stability, decomposing rather than boiling at elevated temperatures. The compound shows typical ketone reactivity including nucleophilic addition reactions, while the amino group participates in diazotization and acylation reactions. In solution, 4-aminoacetophenone exhibits weak basicity (pKa ~2.5) and displays fluorescence properties under UV light. Its UV-Vis spectrum shows strong absorption around 260-280 nm. The material is relatively stable under normal conditions but may darken upon prolonged exposure to light, requiring amber glass containers for long-term storage.
Main Applications
The primary industrial use of 4-aminoacetophenone is as a key intermediate in pharmaceutical manufacturing, particularly for producing antihistamines, local anesthetics, and vasodilators. It serves as the starting material for synthesizing various quinoline and isoquinoline derivatives used in medicinal chemistry. In the dye industry, this compound acts as a precursor for azo dyes and other colorants. Additional applications include use in agrochemical production (especially for certain fungicides) and as a reagent in organic synthesis laboratories. Recent research explores its potential in material science for creating organic semiconductors and photoactive compounds.
Safety and Storage
As an industrial chemical, 4-aminoacetophenone requires careful handling. It may cause eye and skin irritation, and inhalation of dust should be avoided. Appropriate PPE including gloves, goggles, and dust masks is recommended when working with this material. The substance is not considered highly flammable but may combust at high temperatures. For storage, maintain in original tightly sealed containers at room temperature (15-25°C) away from strong oxidizers. Shelf life typically exceeds two years when stored properly. In case of spills, absorb with inert material and dispose according to local regulations. Waste disposal should comply with hazardous chemical protocols.
B2B Procurement Guide
Industrial purchasers should specify required purity (usually 98% min. by HPLC), crystalline form, and moisture content when ordering. Bulk quantities (25kg drums) typically offer better pricing, though smaller R&D quantities (100g-1kg) are available. Key quality indicators include melting point range and absence of colored impurities. Reliable suppliers should provide full analytical certificates (CoA) with each batch, including residual solvent analysis. For international shipments, verify proper hazardous material classification (usually not regulated as dangerous goods for transport). Lead times vary from 2-6 weeks depending on inventory and customization requirements. Consider requesting samples for quality approval before large orders.
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