5-Methoxy-3-methyl-1-benzofuran-2-carbaldehyde is a functionalized benzofuran derivative whose substituted pattern — a methoxy group at the 5-position, a methyl group at the 3-position, and an aldehyde group at the 2-position of the benzofuran core — positions it as a uniquely tailored building block where the 3-methyl provides steric hindrance around the reactive aldehyde, the 5-methoxy offers electronic modulation through resonance donation, and the fused benzofuran core delivers the π-conjugated scaffold essential for biological target interactions.
5-Methoxy-3-methyl-1-benzofuran-2-carbaldehyde (CAS 33038-25-4) is a heterocyclic organic compound belonging to the benzofuran family — a class of fused bicyclic heterocycles consisting of a benzene ring fused to a furan ring . The compound features a methoxy group at the 5-position, a methyl group at the 3-position, and an aldehyde functional group at the 2-position of the benzofuran ring.
In medicinal chemistry, 5-Methoxy-3-methyl-1-benzofuran-2-carbaldehyde serves as a valuable building block for the synthesis of more complex molecules, particularly in the development of new pharmaceuticals and functional materials. Its derivatives have been studied for potential biological activities, including antimicrobial and anticancer properties, with ongoing research exploring its potential as a lead compound for drug development . In biological systems, benzofuran derivatives often interact with molecular targets such as enzymes, receptors, and DNA, leading to the inhibition of enzyme activity, modulation of receptor signaling, or interference with DNA replication and transcription.
Furthermore, 5-Methoxy-3-methyl-1-benzofuran-2-carbaldehyde has demonstrated relevance in diabetes research. Patents (US20120053173A1 and US08436043B2) specifically claim benzofuran derivatives bearing a 5-methoxy-3-methyl substitution pattern as compounds providing superior efficacy for the prophylaxis or treatment of diabetes [9†L16-L25]. The compound is also applicable in the synthesis of dyes, pigments, and other industrial chemicals .
Product Parameters
Parameter
Specification
CAS Number
33038-25-4
Molecular Formula
C₁₁H₁₀O₃
Molecular Weight
190.2 g/mol
Purity
≥95% (HPLC)
Appearance
Pale-yellow to brown solid
Boiling Point
319.8 ± 37.0 °C (Predicted)
Density
1.201 ± 0.06 g/cm³ (Predicted)
Canonical SMILES
CC1=C(OC2=C1C=C(C=C2)OC)C=O
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Each batch undergoes:
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● ¹H NMR – structural verification
● Appearance – colorless to light yellow to light orange clear liquid
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Frequently Asked Questions (FAQ)
Q1: What are the primary applications of 5-Methoxy-3-methyl-1-benzofuran-2-carbaldehyde?
A: This compound serves as a building block in organic synthesis, particularly for the development of new pharmaceuticals and materials. Its derivatives are studied for antimicrobial and anticancer properties, and it is also used in the synthesis of dyes, pigments, and industrial chemicals.
Q2: What pharmaceutical relevance does this compound have?
A: Patents claim that benzofuran derivatives bearing the 5-methoxy-3-methyl substitution pattern, including this compound, possess superior efficacy for the prophylaxis or treatment of diabetes. Research is also ongoing into its potential as a lead compound targeting specific enzymes or receptors.
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