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CS-W001157 4
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2-(Thiophen-3-yl)pyridine

  • CAS No. 21298-55-5

  • Cat. No. CS-W013263
  • Purity≥98%
  • MDL No.MFCD00006214

*For research and further manufacturing use only, not for direct human use.

2-(Thiophen-3-yl)pyridine|CS-W013263

Structure of 21298-55-5

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General Information

  • CAS No. 21298-55-5
  • Cat. No. CS-W013263
  • Purity ≥98%
  • MDL No. MFCD00006214
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₇NS
  • Molecular Weight 161.22
  • Synonym(s) 3-(2-Pyridyl)thiophene
  • SMILES C1(C2=CSC=C2)=NC=CC=C1

Description

2-(Thiophen-3-yl)pyridine features a fused heteroaromatic architecture combining thiophene and pyridine rings, delivering enhanced electron density at the 3-position. This configuration supports robust coordination in transition metal catalysis and facilitates π–π stacking in supramolecular assemblies. The molecule exhibits bench-stable handling and integrates readily into ligand design for palladium-catalyzed cross-coupling reactions.

Application

2-(Thiophen-3-yl)pyridine serves as a versatile heterocyclic building block in medicinal chemistry and materials science, enabling efficient construction of biaryl scaffolds via palladium-catalyzed cross-coupling reactions. Its rigid, planar structure enhances π-stacking interactions in organic semiconductors and contributes to favorable binding geometry in kinase inhibitors. The molecule exhibits good bench stability, moderate solubility in common organic solvents, and tolerance to a range of functional groups, facilitating straightforward purification and integration into multi-step syntheses.

Synthesis

  • Route1

    References

    • Kuraray Co., Ltd. Patent: EP1548005 A1, 2005 ; Location in patent: Page/Page column 12 ;
  • Route2
    • null|null
      109-04-6
    • In-stock
      3-Thienylboronic acid|CS-W001066
      6165-69-1
    • ~97%
    • In-stock
      2-(Thiophen-3-yl)pyridine|CS-W013263
      21298-55-5

    References

    • Wang, Kun; Fu, Qi; Zhou, Rong; Zheng, Xueli; Fu, Haiyan; Chen, Hua; Li, Ruixiang Applied Organometallic Chemistry, 2013 , vol. 27, # 4 p. 232 - 238
  • Route3
    • In-stock
      3-Thienylboronic acid|CS-W001066
      6165-69-1
    • null|null
      57785-86-1
    • ~87%
    • In-stock
      2-(Thiophen-3-yl)pyridine|CS-W013263
      21298-55-5

    References

    • Bhayana, Brijesh; Fors, Brett P.; Buchwald, Stephen L. Organic Letters, 2009 , vol. 11, # 17 p. 3954 - 3957

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319
Precautionary Statements : P264-P280-P302+P352-P362

Quality Control

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Computational Chemistry Data

  • TPSA   12.89
  • LogP   2.8101
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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