Methyl 5-formyl-2-methoxybenzoate
[CAS# 78515-16-9]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ester >> Acid ester compound
• Name: Methyl 5-formyl-2-methoxybenzoate
• Molecular Formula: C₁₀H₁₀O₄
• Molecular Weight: 194.18
• CAS Registry Number: 78515-16-9
• EC Number: 810-013-0
• SMILES: COC1=C(C=C(C=C1)C=O)C(=O)OC

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.544, Calc.^*
• Boiling Point: 332.3±27.0 °C (760 mmHg), Calc.^*
• Flash Point: 148.2±23.8 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

Methyl 5-formyl-2-methoxybenzoate is an organic compound belonging to the class of methoxybenzoates, which are widely studied for their interesting chemical properties and diverse applications. The structure of this compound consists of a methoxy group (-OCH3) and a formyl group (-CHO) attached to a benzene ring, along with a methyl ester group (-COOCH3). The combination of these functional groups imparts unique reactivity to Methyl 5-formyl-2-methoxybenzoate, making it an important intermediate in organic synthesis and potentially valuable in various chemical processes.

The discovery of Methyl 5-formyl-2-methoxybenzoate was driven by the need for versatile building blocks in synthetic chemistry. Its structure, with the formyl and methoxy groups on the benzene ring, allows for easy functionalization, which is useful for designing more complex molecules with specific properties. The formyl group, in particular, is known for its reactivity in organic reactions, such as the synthesis of other aromatic compounds and for introducing aldehyde groups into molecular structures. The methoxy group, on the other hand, is often used to modulate the electronic properties of aromatic compounds, influencing their reactivity and stability.

Methyl 5-formyl-2-methoxybenzoate has found applications in the synthesis of various bioactive molecules, particularly in the development of pharmaceuticals and agrochemicals. The formyl group can be selectively reduced or reacted with other nucleophiles to yield a variety of derivatives with different functional groups. This versatility makes it a useful intermediate in the synthesis of more complex aromatic compounds, which are often the core structures of biologically active molecules. The methoxy group also enhances the solubility and stability of certain derivatives, which is beneficial in drug development and formulation.

In addition to its use in synthetic chemistry, Methyl 5-formyl-2-methoxybenzoate has potential applications in materials science. The compound can be incorporated into the synthesis of novel polymers, dyes, or coatings, where its aromatic structure and functional groups provide stability and desirable properties. Its role as a precursor to other chemical compounds with specific optical or electronic properties further expands its utility in research and industry. Additionally, the compound’s reactivity may be exploited in the design of new materials with applications in sensors, catalysts, and other high-tech industries.

The compound’s ability to undergo a variety of chemical transformations while maintaining its core structure is key to its utility in diverse fields. As research into its applications continues, Methyl 5-formyl-2-methoxybenzoate may see broader use in fields such as pharmaceuticals, materials science, and environmental chemistry. Its combination of reactivity, stability, and versatility ensures that it will remain a valuable compound for synthetic chemists and researchers.

References

2016. Eluxadoline. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-05-0130

2010. The McMurry Reaction. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-045-00165

2010. Of Aldehydes. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-047-00143