📋Basic information:
| Chemical Name | Thieno[2,3-b]pyridine, 4-bromo- |
| Synonyms | 4-bromo-Thieno[2,3-b]pyridine |
| CAS No. | 1305208-22-3 |
| Molecular Formula | C7H4BrNS |
| Molecular Weight | 214.08 |
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📌Specification:
| Appearance | off-white to white powder |
| Boiling Point | 299.8 ± 20.0 °C (at 760 mmHg) |
| Density | 1.748 ± 0.06 g/cm³ |
| Flash Point | 135.1 ± 21.8 °C |
| pKa | 2.95 ± 0.30 |
| Refraction Index | 1.718 |
| Vapor Pressure (25°C) | 0.0 ± 0.6 mmHg |
| Storage | Recommended to store under low temperature, dry, and light-protected conditions. |
🧩Application of Thieno[2,3-b]pyridine, 4-bromo- CAS No.: 1305208-22-3
1. Privileged Scaffold in Medicinal Chemistry
The thieno[2,3-b]pyridine ring system is an important fused heterocyclic scaffold that has attracted significant attention in medicinal chemistry and drug discovery. Combining the electronic properties of both thiophene and pyridine, it serves as a versatile building block for constructing biologically active molecules.
2. Key Synthetic Intermediate
The bromine atom at the 4-position makes this compound an ideal substrate for cross-coupling reactions, including:
- Suzuki coupling (with boronic acids/esters to introduce aryl groups)
- Stille coupling and Negishi coupling
- Buchwald–Hartwig amination
- Ullmann-type reactions
These reactions allow flexible introduction of various substituents at the 4-position, enabling rapid construction of thienopyridine derivative libraries for drug screening.
3. Biological Activity
Thieno[2,3-b]pyridine derivatives reported in the literature exhibit a range of biological activities:
- Antitumor / antiproliferative activity
- Antibacterial and antifungal activity
- Anti-inflammatory activity
- Kinase inhibition (e.g., tyrosine kinase targets)
- Other potential pharmacological activities
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