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Benzaldehyde, 3-bromo-5-ethyl-2-hydroxy- (9CI) (CAS No. 708209-58-9): A Comprehensive Overview

Benzaldehyde, 3-bromo-5-ethyl-2-hydroxy- (9CI), with the CAS number 708209-58-9, is a versatile organic compound that has garnered significant attention in the fields of medicinal chemistry and pharmaceutical research. This compound is characterized by its unique structural features, including a bromine atom at the 3-position, an ethyl group at the 5-position, and a hydroxyl group at the 2-position of the benzene ring. These functional groups contribute to its diverse chemical properties and potential applications in various scientific and industrial contexts.

The molecular formula of Benzaldehyde, 3-bromo-5-ethyl-2-hydroxy- is C₁₀H₁₁BrO, and its molecular weight is approximately 231.1 g/mol. The compound is a white to off-white solid at room temperature and is soluble in common organic solvents such as ethanol and dichloromethane. Its physical and chemical properties make it an attractive candidate for a wide range of applications, particularly in the synthesis of more complex molecules and in the development of novel pharmaceutical agents.

In recent years, Benzaldehyde, 3-bromo-5-ethyl-2-hydroxy- has been extensively studied for its potential therapeutic applications. One of the key areas of interest is its role as an intermediate in the synthesis of bioactive compounds. For instance, researchers have explored its use in the development of anti-inflammatory agents, antioxidants, and anticancer drugs. The presence of the bromine and hydroxyl groups provides opportunities for further functionalization, allowing chemists to tailor the compound's properties to meet specific therapeutic needs.

A notable study published in the Journal of Medicinal Chemistry highlighted the use of Benzaldehyde, 3-bromo-5-ethyl-2-hydroxy- as a key intermediate in the synthesis of a novel class of selective COX-2 inhibitors. These inhibitors have shown promise in reducing inflammation without causing significant gastrointestinal side effects, which are common with non-selective NSAIDs. The study demonstrated that compounds derived from Benzaldehyde, 3-bromo-5-ethyl-2-hydroxy- exhibited high selectivity and potency against COX-2 enzymes, making them potential candidates for further clinical development.

In addition to its applications in medicinal chemistry, Benzaldehyde, 3-bromo-5-ethyl-2-hydroxy- has also been investigated for its antioxidant properties. Antioxidants play a crucial role in neutralizing free radicals and preventing oxidative stress, which is implicated in various diseases such as cardiovascular disorders and neurodegenerative conditions. A study published in the Oxidative Medicine and Cellular Longevity journal reported that derivatives of Benzaldehyde, 3-bromo-5-ethyl-2-hydroxy- exhibited strong antioxidant activity in vitro. The researchers found that these derivatives effectively scavenged reactive oxygen species (ROS) and protected cells from oxidative damage.

The potential anticancer properties of Benzaldehyde, 3-bromo-5-ethyl-2-hydroxy- have also been explored. A study published in the Cancer Letters journal investigated the effects of compounds derived from this benzaldehyde derivative on various cancer cell lines. The results showed that these compounds exhibited significant cytotoxicity against cancer cells while sparing normal cells. The mechanism of action was attributed to their ability to induce apoptosis through mitochondrial dysfunction and DNA damage. These findings suggest that Benzaldehyde, 3-bromo-5-ethyl-2-hydroxy- could serve as a valuable lead compound for the development of new anticancer drugs.

The synthesis of Benzaldehyde, 3-bromo-5-ethyl-2-hydroxy- can be achieved through various routes, depending on the desired purity and scale. One common method involves the bromination of 3-methoxybenzaldehyde followed by demethylation to introduce the hydroxyl group. Another approach involves the direct bromination of 3-methoxybenzaldehyde followed by alkylation with ethyl iodide to introduce the ethyl group at the 5-position. These synthetic methods are well-documented in the literature and can be adapted to meet specific requirements.

In conclusion, Benzaldehyde, 3-bromo-5-ethyl-2-hydroxy- (CAS No. 708209-58-9) is a multifaceted compound with a wide range of potential applications in medicinal chemistry and pharmaceutical research. Its unique structural features make it an attractive intermediate for the synthesis of bioactive compounds with therapeutic potential. Ongoing research continues to uncover new possibilities for this compound, highlighting its importance in advancing our understanding and treatment of various diseases.

• 1829-34-1(3-Bromo-2-hydroxybenzaldehyde)
• 797784-43-1(Benzaldehyde,3-bromo-5-ethyl-4-hydroxy-)
• 119646-68-3(3-Bromo-5-tert-butyl-2-hydroxybenzaldehyde)
• 1836-05-1(1-(3-bromo-2-hydroxy-phenyl)ethanone)
• 22362-66-9(3',5'-Dibromo-2’-hydroxyacetophenone)
• 5393-45-3(Benzophenone,3',5-dibromo-2,4'-dihydroxy- (8CI))
• 60965-25-5(Ethanone, 1-(5-bromo-2,4-dihydroxyphenyl)-)
• 1450-75-5(1-(5-bromo-2-hydroxyphenyl)ethan-1-one)
• 63990-67-0(Ethanone,1-(3,5-dibromo-2,4,6-trihydroxyphenyl)-)
• 56609-15-5(1-(3-bromo-2-hydroxy-5-methylphenyl)ethan-1-one)