Overview
3-Nitro-4-hydroxybenzaldehyde is an organic compound featuring both nitro and hydroxyl functional groups on a benzaldehyde backbone. It serves as a versatile intermediate in chemical synthesis, particularly in pharmaceuticals and dyes. The compound is characterized by its pale yellow crystalline appearance and moderate solubility in polar organic solvents. Its synthesis typically involves nitration of 4-hydroxybenzaldehyde under controlled conditions. Due to its reactive aldehyde group and electron-withdrawing nitro substituent, it participates in various condensation and substitution reactions, making it valuable for producing more complex molecules.
Physical and Chemical Properties
The compound exhibits a melting point range of 150-154°C, indicative of its moderate thermal stability. Its density is approximately 1.5 g/cm³, and it is sparingly soluble in water but dissolves readily in alcohols like ethanol and methanol. The presence of both electron-donating (hydroxyl) and electron-withdrawing (nitro) groups influences its reactivity. In solution, 3-nitro-4-hydroxybenzaldehyde may exhibit tautomerism, with the potential to form quinoid structures under certain conditions. Its UV-visible spectrum typically shows absorption maxima around 300-350 nm, which is useful for analytical identification.
Main Applications
This compound is primarily used as a building block in pharmaceutical synthesis, particularly for drugs targeting cardiovascular and central nervous system disorders. Its nitro group can be reduced to an amine, enabling further derivatization. In the dye industry, it contributes to the synthesis of azo dyes and other colorants. Additionally, 3-nitro-4-hydroxybenzaldehyde finds use in agrochemicals, such as herbicides and fungicides. Researchers also employ it as a ligand in coordination chemistry or as a substrate for enzymatic studies due to its distinct functional groups.
Safety and Storage
As a nitroaromatic compound, 3-nitro-4-hydroxybenzaldehyde requires careful handling. It may cause skin and eye irritation, necessitating gloves, goggles, and lab coats during use. Avoid inhalation of dust and ensure adequate ventilation in workspaces. For storage, keep the material in tightly sealed containers under cool, dry conditions, away from strong oxidizers and reducing agents. Prolonged exposure to light or moisture may degrade the compound, so desiccants and amber glass bottles are recommended for long-term preservation.
B2B Procurement Guide
When sourcing 3-nitro-4-hydroxybenzaldehyde, prioritize suppliers with certifications like ISO or GMP to ensure quality consistency. Request detailed certificates of analysis (CoA) specifying purity (typically 97-99%), residual solvents, and heavy metal content. Bulk buyers should negotiate tiered pricing for orders above 25 kg. Logistics planning is critical due to the compound’s classification as a hazardous material in some regions. Verify shipping regulations and opt for specialized chemical carriers. For international procurement, confirm compliance with REACH, TSCA, or other regional chemical inventories to avoid customs delays.
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