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4-(Methoxymethoxy)benzaldehyde (CAS No. 6515-21-5): An Overview of Its Properties, Applications, and Recent Research

4-(Methoxymethoxy)benzaldehyde (CAS No. 6515-21-5) is a versatile organic compound that has gained significant attention in the fields of organic synthesis, pharmaceutical research, and materials science. This compound, also known as MOM-protected benzaldehyde, is characterized by its unique functional groups and structural properties, which make it an essential building block in various chemical reactions and synthetic pathways.

The molecular formula of 4-(methoxymethoxy)benzaldehyde is C₉H₁₀O₃, and its molecular weight is 166.17 g/mol. The compound features a benzene ring substituted with a methoxymethoxy (MOM) group at the para position and an aldehyde group at the ortho position. The MOM group is a common protecting group used in organic synthesis to temporarily mask hydroxyl groups, thereby preventing unwanted reactions during multi-step syntheses.

In recent years, 4-(methoxymethoxy)benzaldehyde has been extensively studied for its applications in the synthesis of complex organic molecules, including pharmaceuticals and fine chemicals. One of the key advantages of this compound is its ability to undergo selective functionalization and transformation, making it a valuable intermediate in the development of novel drugs and materials.

A notable application of 4-(methoxymethoxy)benzaldehyde is in the synthesis of bioactive compounds. For instance, researchers have utilized this compound as a starting material to synthesize various derivatives with potential therapeutic properties. A recent study published in the Journal of Medicinal Chemistry reported the synthesis of a series of MOM-protected benzaldehyde-based derivatives that exhibited potent anti-inflammatory and anti-cancer activities. These findings highlight the potential of 4-(methoxymethoxy)benzaldehyde as a lead compound for drug discovery.

Beyond its pharmaceutical applications, 4-(methoxymethoxy)benzaldehyde has also found use in materials science. Its unique electronic properties and reactivity make it suitable for the preparation of functional polymers and organic semiconductors. A study published in Advanced Materials demonstrated the use of MOM-protected benzaldehyde-based monomers to create conjugated polymers with enhanced photovoltaic performance. These polymers showed improved charge transport properties and stability, making them promising candidates for next-generation solar cells.

The synthetic versatility of 4-(methoxymethoxy)benzaldehyde is further exemplified by its role in catalytic reactions. Researchers have developed efficient catalytic systems that utilize this compound as a substrate or ligand to achieve high yields and selectivities in various transformations. For example, a palladium-catalyzed cross-coupling reaction involving MOM-protected benzaldehyde-based substrates was reported to yield complex aromatic compounds with high regioselectivity and stereoselectivity.

In addition to its synthetic applications, 4-(methoxymethoxy)benzaldehyde has been studied for its environmental impact and biodegradability. A recent environmental chemistry study investigated the fate and behavior of this compound in aquatic systems. The results indicated that MOM-protected benzaldehyde-based compounds are relatively stable under neutral pH conditions but can be readily degraded by microbial activity under aerobic conditions. This information is crucial for assessing the environmental safety of products derived from this compound.

The physical properties of 4-(methoxymethoxy)benzaldehyde, such as its melting point (63-65°C), boiling point (208°C), and solubility in common organic solvents, make it easy to handle and process in laboratory settings. These properties also contribute to its suitability for large-scale production processes in industrial settings.

In conclusion, 4-(methoxymethoxy)benzaldehyde (CAS No. 6515-21-5) is a multifaceted compound with a wide range of applications in organic synthesis, pharmaceutical research, materials science, and environmental chemistry. Its unique structural features and reactivity profile make it an indispensable tool for chemists working on the development of new molecules and materials. As research continues to advance, it is likely that new applications and insights into the properties of this compound will emerge, further solidifying its importance in the chemical sciences.

• 6515-06-6(3,4-Bis(methoxymethoxy)benzaldehyde)
• 76280-61-0(Benzaldehyde, 3,5-bis(methoxymethoxy)-)
• 342611-03-4(Benzaldehyde-formyl-d,4-(methoxy-d3)- (9CI))
• 19486-71-6(4-Methoxybenzaldehyde-α-d1)
• 95537-93-2(Anisaldehyde-13C)
• 123-11-5(p-Methoxybenzaldehyde)
• 13709-05-2(3-(Methoxymethoxy)benzaldehyde)
• 2652-68-8(Methyl, (4-methoxyphenyl)oxo-)
• 5533-00-6(Benzaldehyde,3-methoxy-4-(methoxymethoxy)-)
• 342611-04-5(4-(Methoxy-d3)benzaldehyde)