7-Bromo-2,3-dihydro-thieno[3,4-b]-1,4-dioxin-5-carboxaldehyde
[CAS# 852054-42-3]

Identification

• Classification: Analytical chemistry >> Food safety >> Dioxins, polychlorinated biphenyls, furans
• Name: 7-Bromo-2,3-dihydro-thieno[3,4-b]-1,4-dioxin-5-carboxaldehyde
• Synonyms: 5-bromo-2,3-dihydrothieno[3,4-b][1,4]dioxine-7-carbaldehyde
• Molecular Formula: C₇H₅BrO₃S
• Molecular Weight: 249.08
• CAS Registry Number: 852054-42-3
• SMILES: C1COC2=C(SC(=C2O1)C=O)Br

Properties

• Solubility: Practically insoluble (0.065 g/L) (25 °C), Calc.^*
• Density: 1.835±0.06 g/cm³ (20 °C 760 Torr), Calc.^*
• Melting point: 141.0-142.0 °C (ethanol )^**
• Index of Refraction: 1.656, Calc.^*
• Boiling Point: 351.5±42.0 °C (760 mmHg), Calc.^*
• Flash Point: 166.4±27.9 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2013 ACD/Labs)

^** Pina, Joao

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

7-Bromo-2,3-dihydro-thieno[3,4-b]-1,4-dioxin-5-carboxaldehyde is a complex organic compound known for its intriguing molecular structure and potential applications in organic synthesis and materials science. It is characterized by a fused heterocyclic system comprising a thieno[3,4-b] ring structure, a 1,4-dioxin group, and a carboxaldehyde functional group, with a bromine atom at the 7-position. This compound, due to its structural features, has garnered attention in both academic and industrial research for its unique reactivity and versatility in various chemical transformations.

The discovery of 7-Bromo-2,3-dihydro-thieno[3,4-b]-1,4-dioxin-5-carboxaldehyde was a result of the ongoing exploration of novel heterocyclic compounds, especially those that combine sulfur-containing aromatic systems with oxygen-rich functional groups. The synthesis of this compound is typically achieved through a multi-step process involving selective functionalization of the thieno[3,4-b]dioxin scaffold, followed by bromination and introduction of the carboxaldehyde group. Researchers sought to develop molecules with enhanced chemical stability, diverse reactivity, and potential for incorporation into more complex materials and medicinal molecules.

One of the primary applications of 7-Bromo-2,3-dihydro-thieno[3,4-b]-1,4-dioxin-5-carboxaldehyde lies in its utility as an intermediate in organic synthesis. The compound can undergo a variety of chemical reactions, including nucleophilic substitution, reduction, and condensation, to yield derivatives with altered functional groups. These derivatives are often sought after in the production of specialty chemicals, pharmaceuticals, and agrochemicals. Specifically, the carboxaldehyde and bromine groups are valuable for introducing further functionalization, which can lead to the synthesis of bioactive molecules with potential applications in drug discovery.

In materials science, this compound's unique heterocyclic structure makes it an attractive candidate for use in the development of organic semiconductors, especially for applications in organic light-emitting diodes (OLEDs) and organic photovoltaic cells (OPVs). The thieno[3,4-b]dioxin scaffold is known to exhibit good electron-donating properties, which are beneficial for creating semiconducting materials with high charge mobility. The bromine atom at the 7-position can also be exploited to tune the electronic properties of the compound and improve its performance in electronic devices.

Furthermore, derivatives of 7-Bromo-2,3-dihydro-thieno[3,4-b]-1,4-dioxin-5-carboxaldehyde have been explored for their potential biological activities. The unique heterocyclic structure has been found to have some degree of pharmacological activity, and studies have indicated that compounds based on this scaffold might exhibit antimicrobial, anticancer, or anti-inflammatory properties. Thus, it is also considered a candidate for further research in the field of medicinal chemistry, where novel compounds with activity against a range of diseases are always in demand.

This compound’s versatility in synthetic chemistry and potential applications in both materials science and medicinal chemistry make it an exciting subject for further research. The ongoing exploration of its derivatives and reaction mechanisms holds promise for the development of advanced functional materials and therapeutic agents, with both commercial and industrial significance.

References

2020. Synthesis and Optical Properties of New Chalcones Containing a 3,4-Ethylenedioxythiophene Fragment. Russian Journal of Organic Chemistry, 56(11).
DOI: 10.1134/s1070428020110056