Overview
3-Chlorocinnamaldehyde is a chlorinated aromatic aldehyde derived from cinnamaldehyde. It serves as a versatile intermediate in organic synthesis, particularly in the production of pharmaceuticals, agrochemicals, and specialty chemicals. Its molecular structure, featuring a chlorine atom at the meta position of the benzene ring, enhances its reactivity in various chemical transformations. This compound is synthesized through chlorination of cinnamaldehyde or via condensation reactions involving chlorobenzaldehyde. Its applications span across industries, including fragrances, where it contributes to unique odor profiles, and medicinal chemistry, where it acts as a building block for active pharmaceutical ingredients (APIs).
Physical and Chemical Properties
3-Chlorocinnamaldehyde appears as a pale yellow to light brown crystalline powder with a characteristic aromatic odor. It has a molecular weight of 166.60 g/mol and a melting point range of 50-55°C. The compound is soluble in common organic solvents like ethanol, acetone, and dichloromethane but exhibits limited solubility in water. Chemically, it undergoes typical aldehyde reactions, including nucleophilic addition and condensation, due to the presence of the formyl group. The chlorine substituent at the 3-position influences its electronic properties, making it a useful intermediate for further functionalization. Stability under normal storage conditions is moderate, though it may degrade upon prolonged exposure to light or moisture.
Main Applications
In the pharmaceutical industry, 3-chlorocinnamaldehyde is employed as a key intermediate in synthesizing compounds with antimicrobial, anti-inflammatory, or anticancer properties. Its structural motif is found in several drug candidates and bioactive molecules. Agrochemical manufacturers utilize this compound to produce pesticides and herbicides, leveraging its reactivity to create chlorinated derivatives with targeted biological activity. Additionally, it finds niche applications in the fragrance industry, where it contributes to complex scent profiles in perfumes and flavorings. Research laboratories also use it as a reagent in organic synthesis projects.
Safety and Storage
3-Chlorocinnamaldehyde requires careful handling due to its irritant properties. Direct contact with skin or eyes can cause inflammation, and inhalation of dust or vapors may lead to respiratory discomfort. Personal protective equipment (PPE), including gloves, goggles, and lab coats, is essential during use. Storage should be in tightly sealed containers, placed in a cool, dry, and well-ventilated area away from light and incompatible substances like strong oxidizers. Shelf life is typically 1-2 years when stored properly. Spills should be contained with inert absorbents and disposed of according to local hazardous waste regulations.
B2B Procurement Guide
When sourcing 3-chlorocinnamaldehyde, prioritize suppliers with certifications (e.g., ISO, GMP) to ensure quality and consistency. Key procurement criteria include purity (≥98%), batch-to-batch uniformity, and compliance with safety documentation (MSDS, COA). Bulk purchases (e.g., 25 kg drums) often offer cost advantages, with prices ranging between $50-$150 per kilogram depending on purity and supplier terms. Consider logistical factors such as shipping conditions (temperature-sensitive) and lead times. Establish long-term contracts with reliable manufacturers to secure stable supply chains, especially for pharmaceutical-grade material.
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