4-Amino-5-chloro-2,3-dihydrobenzo[b]furan-7-carboxylic acid
[CAS# 123654-26-2]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Carboxylic acid
• Name: 4-Amino-5-chloro-2,3-dihydrobenzo[b]furan-7-carboxylic acid
• Synonyms: 4-Amino-5-chloro-2,3-dihydro-7-benzofurancarboxylic acid
• Molecular Formula: C₉H₈ClNO₃
• Molecular Weight: 213.62
• CAS Registry Number: 123654-26-2
• EC Number: 895-293-2
• SMILES: C1COC2=C1C(=C(C=C2C(=O)O)Cl)N

Properties

• Density: 1.6±0.1 g/cm³, Calc.^*, 1.566 (Expl.)
• Index of Refraction: 1.679, Calc.^*
• Boiling Point: 406.5±45.0 °C (760 mmHg), Calc.^*
• Flash Point: 199.6±28.7 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302+H312+H332-H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Discovery and Applications

4-Amino-5-chloro-2,3-dihydrobenzo[b]furan-7-carboxylic acid is a heterocyclic compound with a unique fused benzofuran structure featuring amino, chloro, and carboxylic acid functional groups. Its distinctive framework and reactivity have made it a valuable compound in the development of pharmaceuticals and materials science.

The discovery of this compound arose from research into substituted benzofurans, which are known for their bioactive properties. Synthetic methods for preparing 4-amino-5-chloro-2,3-dihydrobenzo[b]furan-7-carboxylic acid typically involve cyclization reactions of suitably substituted aromatic precursors. These methods allow for precise incorporation of functional groups, ensuring the compound’s versatility for further chemical modifications.

A prominent application of 4-amino-5-chloro-2,3-dihydrobenzo[b]furan-7-carboxylic acid is in medicinal chemistry. The compound’s framework provides a scaffold for designing molecules with potential activity against a range of biological targets. Its amino group can form hydrogen bonds, while the carboxylic acid group interacts with active sites of enzymes or receptors. These properties make it a candidate for developing anti-inflammatory, antimicrobial, or anticancer agents.

In the field of agrochemicals, derivatives of this compound are explored for their potential as herbicides or fungicides. The incorporation of its benzofuran structure into agrochemical formulations can enhance bioavailability and selectivity, contributing to effective pest and disease control in crops.

The compound also has applications in material science. Its functional groups allow for conjugation with polymers or other organic frameworks, leading to the development of advanced materials with specific electronic, optical, or mechanical properties. These materials can find uses in sensors, optoelectronic devices, or as components in sustainable technologies.

The analytical study of 4-amino-5-chloro-2,3-dihydrobenzo[b]furan-7-carboxylic acid relies on techniques such as nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry (MS), and infrared (IR) spectroscopy, which confirm its structure and purity. Advances in these techniques continue to support its effective application in diverse research areas.

Ongoing research into this compound aims to expand its utility in drug discovery and material development. Its versatility and reactivity ensure its relevance in both basic and applied sciences.

References

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