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• Solvents and Organic Chemicals Organic Compounds Acids/Esters

Ethyl 6-bromohexanoate (CAS No. 25542-62-5): A Versatile Compound in Chemical and Pharmaceutical Research

Ethyl 6-bromohexanoate (CAS No. 25542-62-5) is a versatile compound with significant applications in chemical and pharmaceutical research. This ester, characterized by its bromine substituent, has gained attention for its unique properties and potential in various scientific fields. This article provides a comprehensive overview of Ethyl 6-bromohexanoate, including its chemical structure, synthesis methods, and recent research developments.

Chemical Structure and Properties

Ethyl 6-bromohexanoate is an ester of 6-bromohexanoic acid and ethanol. Its molecular formula is C₉H₁₇BrO₂, with a molecular weight of approximately 231.13 g/mol. The compound features a long alkyl chain with a bromine atom at the sixth carbon position, which imparts unique reactivity and functional properties. The presence of the bromine atom makes it an excellent leaving group, facilitating various chemical transformations such as nucleophilic substitution reactions.

The physical properties of Ethyl 6-bromohexanoate include a boiling point of around 180-185°C at reduced pressure and a density of approximately 1.3 g/cm3 at room temperature. It is soluble in common organic solvents such as ethanol, ethyl acetate, and dichloromethane but has limited solubility in water.

Synthesis Methods

The synthesis of Ethyl 6-bromohexanoate can be achieved through several routes, each with its advantages and limitations. One common method involves the esterification of 6-bromohexanoic acid with ethanol in the presence of a catalyst such as sulfuric acid or p-toluenesulfonic acid. The reaction typically proceeds under reflux conditions to ensure complete conversion:

C7H13BrCOOH + C2H5OH → C9H17BrCOOC2H5 + H2O
        

An alternative approach involves the reaction of bromohexanoyl chloride with ethanol, followed by neutralization to form the desired ester:

C7H13BrCOCl + C2H5OH → C9H17BrCOOC2H5 + HCl
        

Ethyl 6-bromohexanoate's versatility in synthesis makes it a valuable intermediate for the preparation of more complex molecules, including pharmaceuticals and fine chemicals.

Ethyl 6-bromohexanoate's unique chemical structure has made it an important reagent in various synthetic pathways. One notable application is in the synthesis of biologically active compounds, where the bromine atom serves as a key functional group for further modification. For example, recent studies have explored the use of Ethyl 6-bromohexanoate-derived intermediates in the preparation of anti-inflammatory agents and anticancer drugs.

In addition to its role in drug discovery, Ethyl 6-bromohexanoate has been utilized in polymer chemistry for the synthesis of functionalized polymers with tailored properties. The bromine atom can be used as a reactive site for controlled radical polymerization techniques, enabling the creation of polymers with specific architectures and functionalities.

The ongoing research on Ethyl 6-bromohexanoate-based compounds has yielded several promising results. A study published in the Journal of Medicinal Chemistry reported the synthesis and biological evaluation of novel derivatives derived from Ethyl 6-bromohexanoate. These derivatives exhibited potent anti-inflammatory activity and were found to be effective in reducing inflammation in animal models.

In another study, researchers from the University of California explored the use of Ethyl 6-bromohexanoate-based monomers in the development of stimuli-responsive hydrogels. The resulting hydrogels demonstrated excellent biocompatibility and responsiveness to environmental changes, making them suitable for drug delivery applications.

Beyond medicinal chemistry, there is growing interest in using Ethyl 6-bromohexanoate-derived materials for environmental remediation. A recent study published in Environmental Science & Technology demonstrated that polymers synthesized from Ethyl 6-bromohexanoate-based monomers could effectively remove heavy metals from contaminated water sources.

Ethyl 6-bromohexanoate (CAS No. 25542-62-5) is a multifaceted compound with a wide range of applications in chemical and pharmaceutical research. Its unique chemical structure and reactivity make it an invaluable reagent for synthetic chemists working on drug discovery, polymer science, and environmental remediation projects. As research continues to advance, it is likely that new applications for this versatile compound will emerge, further solidifying its importance in the scientific community.

• 821015-82-1(Octanedioic acid, 8-bromooctyl ethyl ester)
• 819883-44-8(Octanoic acid, 8-bromo-, 12-hydroxydodecyl ester)
• 71648-29-8(Tetradecanoic acid,bromo-, ethyl ester (9CI))
• 821015-79-6(Pentanedioic acid, 4-bromobutyl hexyl ester)
• 6271-23-4(Ethyl 11-Bromoundecanoate)
• 821015-81-0(Pentanedioic acid, 6-bromohexyl decyl ester)
• 821015-80-9(Pentanedioic acid, 6-bromohexyl hexyl ester)
• 819883-43-7(Octanoic acid, 8-bromo-, 11-hydroxyundecyl ester)
• 819883-42-6(Octanoic acid, 8-bromo-, 10-hydroxydecyl ester)
• 87213-55-6(Hexanoic acid, 6-bromo-, 1,6-hexanediyl ester)