3-Bromo-5-(tert-butyl)benzo[b]thiophene
[CAS# 1780644-81-6]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Thiophene compound
• Name: 3-Bromo-5-(tert-butyl)benzo[b]thiophene
• Molecular Formula: C₁₂H₁₃BrS
• Molecular Weight: 269.20
• CAS Registry Number: 1780644-81-6
• SMILES: CC(C)(C)C1=CC2=C(C=C1)SC=C2Br

Properties

• Density: 1.4±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.617, Calc.^*
• Boiling Point: 327.7±22.0 ºC (760 mmHg), Calc.^*
• Flash Point: 152.0±22.3 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P280-P301+P312-P302+P352-P305+P351+P338

Discovory and Applicatios

The discovery of 3-bromo-5-(tert-butyl)benzo[b]thiophene stems from the search for benzo[b]thiophene derivatives with improved chemical and physical properties. Benz[b]thiophene has aromaticity and a sulfur-containing ring system, providing a basis for creating compounds with desirable electronic properties. The synthesis of 3-bromo-5-(tert-butyl)benzo[b]thiophene involves the bromination of 5-(tert-butyl)benzo[b]thiophene. This process proceeds via an electrophilic substitution reaction, introducing a bromine atom into the aromatic ring. The tert-butyl group is a bulky substituent that enhances the compound's solubility in organic solvents and influences its stereogenic properties, making it a useful intermediate for further chemical modifications.

3-Bromo-5-(tert-butyl)benzo[b]thiophene is a versatile building block in organic synthesis. Its bromine atom provides an entry point for cross-coupling reactions, allowing for the formation of carbon-carbon bonds necessary to build complex molecular structures. This feature is valuable in the synthesis of drugs and natural product analogs.

The compound is frequently used in palladium-catalyzed cross-coupling reactions such as Suzuki-Miyaura and Stille couplings. These reactions allow for the formation of a wide variety of molecular structures by attaching aromatic or other functional units to the benzo[b]thiophene core. The tert-butyl group ensures stability and influences the reaction pathway, thereby improving yield and selectivity.

As a precursor, 3-bromo-5-(tert-butyl)benzo[b]thiophene can be further functionalized to introduce a variety of substituents at the 3-position. This versatility allows the synthesis of a wide range of benzo[b]thiophene derivatives with tailored electronic and stereogenic properties for specific applications in materials science and pharmaceuticals.

In materials science, 3-bromo-5-(tert-butyl)benzo[b]thiophene is used in the development of organic electronic materials, including organic semiconductors and light-emitting diodes (OLEDs). Its aromatic structure and the presence of sulfur facilitate the formation of materials with favorable electronic properties, such as high charge mobility and fluorescence. These materials are essential for the development of flexible electronics and advanced display technologies.

The benzo[b]thiophene core of the compound has also been explored in the synthesis of conducting polymers. These polymers exhibit unique electronic properties that make them suitable for applications in sensors, transistors, and photovoltaic cells. The tert-butyl group affects the polymerization process, allowing control over the polymer's structure and electronic properties.

In pharmaceuticals, 3-bromo-5-(tert-butyl)benzo[b]thiophene serves as a scaffold for drug discovery. Its ability to undergo a variety of chemical transformations allows for the development of novel drug candidates targeting different biological pathways. The compound's structure can be modified to enhance binding affinity and specificity, making it a valuable tool in medicinal chemistry.

Research on benzo[b]thiophene derivatives, including 3-bromo-5-(tert-butyl)benzo[b]thiophene, has shown potential for the development of anticancer agents. These compounds can interfere with cancer cell proliferation and induce apoptosis. The bromine atom enhances their ability to interact with biological targets, contributing to their efficacy as potential cancer therapeutics.