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2-Bromo-6-methoxybenzene-1,4-diol (CAS No. 61654-67-9): A Comprehensive Overview

2-Bromo-6-methoxybenzene-1,4-diol, also known by its CAS registry number CAS No. 61654-67-9, is a structurally unique aromatic compound with significant applications in various fields of chemistry and pharmacology. This compound is characterized by its bromine atom at the 2-position, a methoxy group at the 6-position, and hydroxyl groups at the 1 and 4 positions of the benzene ring. Its molecular formula is C₈H₇BrO₃, and it has a molecular weight of approximately 235.08 g/mol.

The synthesis of 2-Bromo-6-methoxybenzene-1,4-diol typically involves multi-step organic reactions, often starting from substituted phenols or anisoles. The introduction of the bromine atom is achieved through electrophilic substitution reactions, while the hydroxyl groups are either retained from the starting material or introduced via oxidation or hydrolysis steps. The presence of both electron-donating methoxy and electron-withdrawing bromine groups creates a unique electronic environment on the benzene ring, which influences its reactivity and selectivity in various chemical transformations.

Recent studies have highlighted the potential of CAS No. 61654-67-9 as a versatile building block in medicinal chemistry. Its dihydroxy structure makes it a valuable precursor for the synthesis of bioactive molecules, including antioxidants, anti-inflammatory agents, and potential anticancer drugs. For instance, researchers have explored its use in constructing polyphenolic frameworks that mimic natural products with known therapeutic benefits.

In terms of chemical properties, 2-Bromo-6-methoxybenzene-1,4-diol exhibits moderate solubility in polar solvents such as water and ethanol due to its hydrophilic functional groups. It is relatively stable under ambient conditions but can undergo oxidation or elimination reactions under specific conditions. The compound's UV-vis spectrum shows strong absorption bands in the ultraviolet region, which is attributed to its conjugated aromatic system and electron-withdrawing substituents.

The application of CAS No. 61654-67-9 extends beyond pharmaceuticals into materials science. Its ability to form hydrogen bonds and participate in coordination chemistry makes it a promising candidate for designing supramolecular assemblies and functional materials. Recent advancements in green chemistry have also led to the exploration of this compound as an eco-friendly catalyst in organic transformations.

In conclusion, 2-Bromo-6-methoxybenzene-1,4-diol (CAS No. 61654-67-9) stands out as a multifaceted compound with diverse applications across various scientific disciplines. Its unique structure and reactivity continue to inspire innovative research directions, solidifying its position as an essential molecule in modern chemical science.

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