3-BroMo-4,5-diMethoxybenzaldehyde

3-Bromo-4,5-dimethoxybenzaldehyde is a versatile aromatic aldehyde and pharmaceutical intermediate extensively utilized as a key building block in the synthesis of complex heterocycles and biologically active small molecules. As a key synthetic precursor, 3-Bromo-4,5-dimethoxybenzaldehyde has been employed as a reagent to synthesize aromatic vinyl sulfones — compounds that act as inhibitors of HIV-1 — and as a key building block in the total synthesis of (−)-Tejedine, a secobisbenzylisoquinoline natural product found in Barberry (Berberis species, a medicinal plant) with potential therapeutic applications. 3-Bromo-4,5-dimethoxybenzaldehyde has also been investigated for its potential biological activities, including antimicrobial and anticancer properties, and has been shown to increase the protein and mRNA levels of glutathione‑synthesizing enzymes, thereby enhancing reduced glutathione production in human keratinocytes. The synthetic utility and biological relevance of 3-Bromo-4,5-dimethoxybenzaldehyde have positioned it as a common reagent in the construction of proaporphine and homoproaporphine‑type alkaloids and as a valuable precursor for the synthesis of pharmaceutical intermediates and other functionalized aromatic compounds.

Product Parameters

FAQ

Q1:What is the primary application of this compound in medicinal chemistry?

A: 3-Bromo-4,5-dimethoxybenzaldehyde has two principal medicinal chemistry applications: as a reagent for synthesizing aromatic vinyl sulfones, which have been shown to act as inhibitors of HIV‑1, and as a key building block in the total synthesis of (−)-Tejedine, a secobisbenzylisoquinoline natural product found in Barberry (Berberis species), a plant used in traditional medicine systems.

Q2: How does the bromine substitution pattern affect reactivity?

A: The bromine atom at the 3‑position (adjacent to the 4‑methoxy group) provides a handle for cross‑coupling reactions (e.g., Suzuki–Miyaura, Buchwald–Hartwig). The 4,5‑dimethoxy groups are electron‑donating, activating the aromatic ring toward electrophilic aromatic substitution while also influencing the reactivity of the aldehyde group through resonance and inductive effects.

Storage Conditions

Store 3-Bromo-4,5-dimethoxybenzaldehyde in a tightly sealed container under refrigerated conditions at 2–8 °C. Keep the container dry, protected from light, and stored in a clean, well‑ventilated area away from strong oxidizing agents, strong bases, and sources of ignition. The crystalline solid is stable under recommended storage conditions. Avoid prolonged exposure to humid air, as moisture may cause caking or accelerate degradation. Do not freeze.

Shelf life: 2 years when stored as recommended in a sealed container under refrigerated conditions, protected from light. Accelerated stability data (40 °C / 75 % RH) and long‑term stability summaries are available upon request to support regulatory filings.

Handling precautions: Use only in a fume hood. Wear chemical‑resistant gloves (tested against EN 374 or equivalent), safety goggles, and a lab coat. Avoid generating dust or aerosols. Do not eat, drink or smoke in work areas. After handling, wash hands thoroughly. Contaminated clothing should be removed and washed before reuse. Refer to the Safety Data Sheet (SDS) for complete safety information.

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