3-Bromothieno[2,3-b]pyridine

Name: 3-Bromothieno[2,3-b]pyridine
Brand: ChemScene
Availability: InStock
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CAS No. 28988-21-8
Cat. No. CS-W006726
Purity≥96%
MDL No.MFCD11869739

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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Structure of 28988-21-8

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General Information

CAS No. 28988-21-8
Cat. No. CS-W006726
Purity ≥96%
MDL No. MFCD11869739
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₇H₄BrNS
Molecular Weight 214.08
Synonym(s) NSC 152393
SMILES BrC1=CSC2=NC=CC=C21

Description

3-Bromothieno[2,3-b]pyridine is a heteroaromatic building block featuring a brominated thienopyridine core. This scaffold integrates a reactive halogen site with extended π-conjugation, enabling direct functionalization in cross-coupling reactions. The molecule exhibits enhanced stability and solubility in organic media, facilitating its use in pharmaceutical synthesis and materials chemistry.

Application

3-Bromothieno[2,3-b]pyridine serves as a versatile building block in heterocyclic synthesis, enabling palladium-catalyzed cross-coupling reactions for the construction of biologically relevant scaffolds. Its bromine substituent offers high reactivity in standard Suzuki, Stille, and Negishi transformations, while the fused thienopyridine core provides enhanced planarity and electron-rich character. The compound exhibits excellent bench stability and facilitates straightforward purification, making it well-suited for iterative medicinal chemistry campaigns and process-scale applications.

Synthesis

Route1
- In-stock
  
  272-23-1
- ~47%
- In-stock
  
  28988-21-8
References
- ELI LILLY AND COMPANY Patent: WO2006/107784 A1, 2006 ; Location in patent: Page/Page column 94 ; WO 2006/107784 A1

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

TPSA 12.89
LogP 3.0588
H_Acceptors 2
H_Donors 0
Rotatable_Bonds 0

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Building Blocks Skeleton Aromatic heterocycle compounds Thiophene compounds

Key Words

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3-Bromothieno[2,3-b]pyridine

CAS No. 28988-21-8

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