5-bromo-3-methylbenzofuran-2-carbaldehyde

5-bromo-3-methylbenzofuran-2-carbaldehyde (CAS 57329-38-1) is a member of the benzofuran family — a fused heterocyclic system consisting of a benzene ring fused to a furan ring. The presence of a bromine atom at the 5-position, a methyl group at the 3-position, and an aldehyde group at the 2-position gives this compound a unique substitution pattern that is valuable for chemical transformations and biological applications. The molecular formula is C₁₀H₇BrO₂ with a molecular weight of 239.07 g/mol, and the compound is supplied as a pale yellow to off-white crystalline solid.

In medicinal chemistry, 5-bromo-3-methylbenzofuran-2-carbaldehyde is a privileged scaffold. The benzofuran core is widely recognized as a privileged structure in drug discovery due to its ability to mimic the structural motifs of bioactive natural products and interact with diverse biological targets such as kinases and receptors.  Benzofuran derivatives have been reported to possess a wide spectrum of biological activities, including antidepressant, anticancer, antiviral, antifungal, antioxidant, and anti-psychotic properties. Substituted benzofurans also find applications as fluorescent sensors, brightening agents, and in various agricultural fields.

6-Bromo-3-methyl-1-benzofuran-2-carbaldehyde serves as a key building block in the synthesis of bromodomain inhibitors, which are promising therapeutic agents for the treatment of acute and chronic autoimmune and inflammatory conditions, viral infections, and cancer.  Additionally, 5-bromo-3-methylbenzofuran-2-carbaldehyde can be used in the synthesis of neurogenesis-promoting agents, which exhibit low phototoxicity and high ability to transfer to the central nervous system, making them relevant for research into neurodegenerative diseases such as Alzheimer‘s disease.

Product Parameters

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Synthetic Routes

Several methods have been documented for the synthesis of 5-bromo-3-methylbenzofuran-2-carbaldehyde. The most common approach involves the regioselective bromination of 3-methyl-1-benzofuran-2-carbaldehyde.

Method 1: Bromination of 3-Methyl-1-benzofuran-2-carbaldehyde

The synthesis typically involves the bromination of 3-methyl-1-benzofuran-2-carbaldehyde using bromine or N-bromosuccinimide (NBS) as the brominating agent in a suitable solvent like dichloromethane. The reaction is carried out at room temperature or slightly elevated temperatures to ensure complete bromination. The electron-withdrawing aldehyde group directs the electrophilic substitution to the 5-position of the benzofuran ring, achieving high regioselectivity.

Method 2: Industrial Production Methods

Industrial production may involve similar synthetic routes but on a larger scale. The use of continuous flow reactors and automated systems enhances the efficiency and yield of the production process. Purification steps such as recrystallization or column chromatography are employed to obtain the compound in high purity.

Frequently Asked Questions (FAQ)

Q1: What are the primary applications of 5-bromo-3-methylbenzofuran-2-carbaldehyde?

A: It is primarily used as a building block in medicinal chemistry (synthesis of bromodomain inhibitors and neurogenesis‑promoting agents), in organic synthesis for constructing complex molecules, as a research compound for biological studies, and as a precursor for fluorescent sensors and materials science applications.

Q2: Is this compound suitable for research into neurodegenerative diseases?

A: Yes. Derivatives of benzofuran compounds have been reported to promote neurogenesis and nerve cell regeneration with low phototoxicity and high ability to transfer to the central nervous system, making the scaffold relevant for research into neurodegenerative diseases such as Alzheimer‘s disease.

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