Methyl 4-(acetylamino)-5-chloro-2,3-dihydrobenzofuran-7-carboxylate
[CAS# 143878-29-9]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: Methyl 4-(acetylamino)-5-chloro-2,3-dihydrobenzofuran-7-carboxylate
• Molecular Formula: C₁₂H₁₂ClNO₄
• Molecular Weight: 269.68
• CAS Registry Number: 143878-29-9
• EC Number: 604-385-1
• SMILES: CC(=O)NC1=C(C=C(C2=C1CCO2)C(=O)OC)Cl

Properties

• Solubility: Very slightly soluble (0.32 g/L) (25 °C), Calc.^*
• Density: 1.400±0.06 g/cm³ (20 °C 760 Torr), Calc.^*
• Index of Refraction: 1.606, Calc.^*
• Boiling Point: 492.0±45.0 °C (760 mmHg), Calc.^*
• Flash Point: 251.4±28.7 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H317
• Safety Statements: P261-P272-P280-P302+P352-P321-P333+P317-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin sensitization	Skin Sens.	1	H317

Discovery and Applications

Methyl 4-(acetylamino)-5-chloro-2,3-dihydrobenzofuran-7-carboxylate is an organic compound that features a complex benzofuranone structure, incorporating an acetylamino group, a chloro substituent, and a carboxylate ester functionality. This compound is of interest in both synthetic organic chemistry and medicinal chemistry due to its potential as a bioactive molecule and its structural resemblance to various naturally occurring compounds.

The discovery of methyl 4-(acetylamino)-5-chloro-2,3-dihydrobenzofuran-7-carboxylate occurred as part of broader efforts to explore bioactive benzofuran derivatives. These types of compounds have been known for their diversity in biological activity, including antimicrobial, anti-inflammatory, and anticancer properties. The structural features of methyl 4-(acetylamino)-5-chloro-2,3-dihydrobenzofuran-7-carboxylate suggest it could interact with biological targets in a manner similar to other pharmacologically relevant benzofuran compounds.

One of the primary applications of methyl 4-(acetylamino)-5-chloro-2,3-dihydrobenzofuran-7-carboxylate lies in medicinal chemistry. Researchers have investigated the compound for its potential therapeutic effects, particularly as an anti-inflammatory or antimicrobial agent. The presence of the acetylamino group enhances its ability to engage in hydrogen bonding, which can influence its binding to target receptors or enzymes. The chloro group further modifies the molecule's reactivity, allowing it to potentially interact with specific biological targets involved in inflammation and infection pathways. Thus, it may have utility in drug development for treating diseases associated with these conditions.

In addition to its pharmaceutical applications, the compound has been used in synthetic organic chemistry as a building block for more complex molecules. Its structure makes it suitable for further modification to create derivatives with enhanced biological activity or altered chemical properties. As a carboxylate ester, it can participate in esterification reactions, and the chloro group enables various substitution reactions. These properties make it a versatile intermediate in the synthesis of other functionalized benzofuranone derivatives.

Another application of methyl 4-(acetylamino)-5-chloro-2,3-dihydrobenzofuran-7-carboxylate is in the development of materials with unique chemical properties. The benzofuranone core structure is valuable in the design of organic semiconductors and materials for optoelectronic devices, where the functionality of the substituents, such as the acetylamino and chloro groups, can modify the electronic properties of the material. This could enable the development of new types of sensors, light-emitting diodes, or photovoltaic materials.

The compound’s reactivity and versatility also make it a candidate for use in chemical sensing applications, where its functional groups could be used to detect or quantify certain analytes in the environment. The ease with which methyl 4-(acetylamino)-5-chloro-2,3-dihydrobenzofuran-7-carboxylate can undergo chemical transformations allows researchers to tailor its properties for a range of technological applications.

As with other chemical substances, handling methyl 4-(acetylamino)-5-chloro-2,3-dihydrobenzofuran-7-carboxylate requires care due to its potentially reactive nature, particularly when exposed to moisture or strong bases. Proper storage conditions and protective measures are essential to maintaining the stability of the compound and ensuring its successful application in both research and industrial settings.

References

2020. Prucalopride. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-16-0282