4-Methoxycarbonylmethylbenzoic acid methyl ester
[CAS# 52787-14-1]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: 4-Methoxycarbonylmethylbenzoic acid methyl ester
• Synonyms: Methyl 4-(2-methoxy-2-oxoethyl)benzoate; Methyl 4-methoxycarbonylphenylacetate
• Molecular Formula: C₁₁H₁₂O₄
• Molecular Weight: 208.21
• CAS Registry Number: 52787-14-1
• EC Number: 692-016-5
• SMILES: COC(=O)CC1=CC=C(C=C1)C(=O)OC

Properties

• Density: 1.155±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.511, Calc.^*
• Boiling Point: 298.0±23.0 °C (760 mmHg), Calc.^*, 97-99 °C (0.01 mmHg) (Expl.)
• Flash Point: 145.4±21.0 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H319
• Safety Statements: P264+P265-P280-P305+P351+P338-P337+P317

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

4-Methoxycarbonylmethylbenzoic acid methyl ester, also known as methyl 4-methoxycarbonylmethylbenzoate, is an organic compound with a benzene ring substituted with both a methoxycarbonyl group and a methyl ester group. The compound plays an important role in organic synthesis, offering versatile reactivity due to its functional groups, which include an ester, a methoxy group, and a carboxyl group. These features make it an interesting candidate for a variety of applications, particularly in the fields of materials science, pharmaceutical development, and chemical synthesis.

The discovery of 4-methoxycarbonylmethylbenzoic acid methyl ester is part of the ongoing efforts to develop molecules with multifunctional properties. The combination of ester and methoxycarbonyl functionalities within the molecule is significant in synthetic organic chemistry. It enables the compound to serve as both an intermediate and a reagent in reactions aimed at creating other complex molecules. Its synthesis often involves the reaction of 4-carboxymethylbenzoic acid with methanol in the presence of a catalyst, followed by esterification.

One of the key applications of 4-methoxycarbonylmethylbenzoic acid methyl ester lies in the field of pharmaceutical chemistry. Its structure, which combines both ester and carboxyl functionalities, allows it to interact with various biological targets. Researchers have explored its use in drug design, where it can serve as a building block for the creation of bioactive compounds. Its methoxy and ester groups contribute to its solubility and stability, making it a potential candidate for use in formulations designed for drug delivery or for enhancing the bioavailability of certain pharmaceutical agents.

4-Methoxycarbonylmethylbenzoic acid methyl ester is also applied in the synthesis of polymeric materials. The ester group within the molecule makes it suitable for incorporation into polymer chains, where it can act as a comonomer. This inclusion can modify the properties of the resulting polymer, such as its solubility, flexibility, and thermal stability. The compound can be used in the production of specialty polymers for applications such as coatings, adhesives, and packaging materials.

Moreover, 4-methoxycarbonylmethylbenzoic acid methyl ester plays a role in the field of agrochemicals. Researchers have investigated its potential as an intermediate for the synthesis of herbicides, fungicides, and other plant-protecting agents. The ester group enhances the compound's ability to penetrate plant tissues, while the carboxyl group provides additional reactivity that can be harnessed in the development of agrochemical formulations designed to target specific biological pathways in plants.

References

2017. Direct amidation of esters with nitroarenes. Nature Communications, 8.
DOI: 10.1038/ncomms14878

2011. Pralatrexate. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-16-0264