3-Bromodibenzothiophene
[CAS# 97511-04-1]

Identification

• Classification: Pharmaceutical intermediate >> OLED material intermediate
• Name: 3-Bromodibenzothiophene
• Synonyms: 3-Bromodibenzo[b,d]thiophene
• Molecular Formula: C₁₂H₇BrS
• Molecular Weight: 263.15
• CAS Registry Number: 97511-04-1
• EC Number: 815-535-2
• SMILES: C1=CC=C2C(=C1)C3=C(S2)C=C(C=C3)Br

Properties

• Solubility: Insoluble (1.8E^-4 g/L) (25 °C), Calc.^*
• Density: 1.611±0.06 g/cm³ (20 °C 760 Torr), Calc.^*
• Melting point: 203-205 °C^**

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2018 ACD/Labs)

^** Ishihara, Tsukasa

Safety Data

• Hazard Symbols: GHS07;GHS09 Warning
• Risk Statements: H302-H410
• Safety Statements: P264-P270-P273-P301+P317-P330-P391-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410

Discovery and Applications

3-Bromodibenzothiophene is an organobromine compound with a dibenzothiophene core structure where a bromine atom is substituted at the third position on the thiophene ring. This compound represents an important class of chemicals due to its unique structural features and its versatile applications in organic synthesis and materials science.

The discovery of 3-bromodibenzothiophene is part of the broader investigation into dibenzothiophene derivatives, which have been studied for their interesting electronic and chemical properties. Dibenzothiophene itself is a polycyclic aromatic compound featuring a thiophene ring fused with two benzene rings. The introduction of a bromine atom into this structure enhances its reactivity, particularly in the context of substitution reactions and cross-coupling processes.

One of the primary applications of 3-bromodibenzothiophene is in organic synthesis, where it serves as a crucial intermediate for the preparation of various complex molecules. The bromine atom in the molecule acts as a reactive site for palladium-catalyzed cross-coupling reactions, such as the Suzuki-Miyaura coupling and the Heck reaction. These reactions allow for the formation of carbon-carbon bonds with other aromatic or vinyl groups, facilitating the synthesis of diverse organic compounds. This reactivity makes 3-bromodibenzothiophene a valuable building block in the creation of new materials and pharmaceuticals.

In the field of materials science, 3-bromodibenzothiophene is used as a precursor for the development of organic semiconductors. The dibenzothiophene structure provides a rigid, planar framework that is beneficial for charge transport in electronic devices. By incorporating 3-bromodibenzothiophene into polymeric materials or small molecule semiconductors, researchers can design materials with tailored electronic properties for use in organic light-emitting diodes (OLEDs), organic photovoltaics (OPVs), and field-effect transistors (OFETs). The bromine substitution enhances the electronic interactions within the material, contributing to improved performance in these applications.

Additionally, 3-bromodibenzothiophene has been explored for its potential in organic electronics and optoelectronics. The compound's ability to participate in various chemical reactions makes it a versatile component in the synthesis of organic electronic materials. For instance, it can be used to modify the properties of organic semiconductors by incorporating different functional groups or by creating copolymers with other electron-rich or electron-deficient units. This versatility allows for the fine-tuning of the material's electronic and optical properties, leading to advancements in electronic devices and sensors.

In the realm of chemical research, 3-bromodibenzothiophene is also used as a model compound to study the reactivity and properties of dibenzothiophene derivatives. Its reactivity in various chemical transformations provides insights into the behavior of similar compounds, contributing to a better understanding of the underlying principles governing organic reactions and material properties.

The ongoing research into 3-bromodibenzothiophene underscores its significance in both fundamental and applied chemistry. As scientists continue to explore its reactivity and applications, this compound remains an important tool in the development of new materials and technologies. Its role in organic synthesis, materials science, and optoelectronics ensures its continued relevance in advancing the field of chemistry.

References

2024. Exploring the effects of mono-bromination on hole-electron transport and distribution in dibenzofuran and dibenzothiophene isomers: a first-principles study. Journal of Molecular Modeling, 30(6).
DOI: 10.1007/s00894-024-05966-5

2020. Homogeneous Gold-Catalyzed Aryl-Aryl Coupling Reactions. Synthesis, 52(7).
DOI: 10.1055/s-0039-1690882

2001. Reduction of Dibenzothiophene 5-Oxides and 5,5-Dioxides. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-010-00343