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• 2. An astrophysically-relevant mechanism for amino acid enantiomer enrichment
  Stephen P. Fletcher,Richard B. C. Jagt,Ben L. Feringa Chem. Commun., 2007, 2578-2580
• 3. An amorphous lanthanum–iridium solid solution with an open structure for efficient water splitting?
  Wei Sun,Chenglong Ma,Xinlong Tian,Jianjun Liao,Ji Yang,Chengjun Ge,Weiwei Huang J. Mater. Chem. A, 2020,8, 12518-12525
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• Solvents and Organic Chemicals Organic Compounds Organic oxygen compounds Organooxygen compounds Carbonyl compounds Aldehydes

4-Bromo-3-Hydroxybenzaldehyde: A Comprehensive Overview

4-Bromo-3-hydroxybenzaldehyde, also known by its CAS number 20035-32-9, is a compound of significant interest in various fields of chemistry and biology. This aromatic aldehyde is characterized by its bromine atom at the para position and a hydroxyl group at the meta position relative to the aldehyde functional group. The compound has been extensively studied for its unique chemical properties, biological activities, and potential applications in drug discovery and material science.

The synthesis of 4-bromo-3-hydroxybenzaldehyde has been explored through various methodologies, including oxidative coupling reactions and directed metallation strategies. Recent advancements in catalytic systems have enabled more efficient and environmentally friendly routes to this compound. For instance, researchers have utilized palladium-catalyzed cross-coupling reactions to synthesize this aldehyde with high yields and excellent regioselectivity. These methods not only enhance the scalability of production but also align with the growing demand for sustainable chemical processes.

In terms of biological activity, 4-bromo-3-hydroxybenzaldehyde has demonstrated potent anti-inflammatory and antioxidant properties. Studies have shown that the compound can effectively inhibit the production of reactive oxygen species (ROS) and modulate key inflammatory pathways, making it a promising candidate for the development of novel anti-inflammatory agents. Furthermore, recent research has highlighted its potential as a chemopreventive agent against oxidative stress-related diseases, such as neurodegenerative disorders and cardiovascular diseases.

The structural features of 4-bromo-3-hydroxybenzaldehyde also make it an attractive building block in organic synthesis. Its aldehyde group provides reactivity for various condensation reactions, while the bromine atom offers opportunities for further functionalization through nucleophilic aromatic substitution or coupling reactions. For example, researchers have employed this compound as a precursor for synthesizing bioactive heterocycles, such as isoquinolines and quinazolines, which are known for their anticancer and antimicrobial activities.

In addition to its biological applications, 4-bromo-3-hydroxybenzaldehyde has found utility in materials science. Its ability to form stable coordination complexes with transition metals has been exploited in the development of novel catalysts for organic transformations. Recent studies have demonstrated its effectiveness as a ligand in asymmetric catalysis, enabling the enantioselective synthesis of chiral molecules with high optical purity.

The growing interest in 4-bromo-3-hydroxybenzaldehyde is also driven by its role as a key intermediate in natural product synthesis. For instance, it has been used as a starting material for synthesizing complex polyphenolic compounds found in plants, which are known for their health-promoting properties. This underscores the importance of understanding the chemical properties and reactivity of this compound to facilitate its application in natural product total synthesis.

In conclusion, 4-bromo-3-hydroxybenzaldehyde, with its unique structural features and diverse reactivity, continues to be a focal point in chemical research. Its potential applications span across drug discovery, materials science, and natural product synthesis, making it a versatile molecule with significant scientific and commercial value. As research progresses, new insights into its properties and applications are expected to emerge, further solidifying its importance in the chemical sciences.

• 1829-34-1(3-Bromo-2-hydroxybenzaldehyde)
• 16414-34-9(3-Bromo-4,5-dihydroxybenzaldehyde)
• 196081-71-7(2-bromo-3-hydroxy-benzaldehyde)
• 2973-77-5(3,5-Dibromo-4-hydroxybenzaldehyde)
• 2973-78-6(3-Bromo-4-hydroxybenzaldehyde)
• 2737-22-6(2,4,6-Tribromo-3-Hydroxybenzaldehyde)
• 31558-40-4(4-Bromo-3,5-dimethoxybenzaldehyde)
• 16534-12-6(4-Bromo-3,5-dihydroxybenzoic acid)
• 14847-51-9(2-Bromo-5-methylphenol)
• 14348-38-0(4-Bromo-3-hydroxybenzoic acid)