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CS-W001157 4
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2-((Trimethylsilyl)ethynyl)pyridine

  • CAS No. 86521-05-3

  • Cat. No. CS-W017437
  • Purity≥98%
  • MDL No.MFCD00066349

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

2-((Trimethylsilyl)ethynyl)pyridine|CS-W017437

Structure of 86521-05-3

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General Information

  • CAS No. 86521-05-3
  • Cat. No. CS-W017437
  • Purity ≥98%
  • MDL No. MFCD00066349
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₁₃NSi
  • Molecular Weight 175.31
  • Synonym(s) 2-(Trimethylsilylethynyl)pyridine
  • SMILES C[Si](C)(C)C#CC1=CC=CC=N1

Description

This pyridine derivative features a trimethylsilyl-protected alkyne group, enabling stable, bench-ready coupling in Sonogashira reactions. The silyl moiety enhances solubility and prevents premature reaction, while the pyridine nitrogen provides a handle for further functionalization.

Application

2-((Trimethylsilyl)ethynyl)pyridine serves as a versatile building block in transition-metal-catalyzed coupling reactions, enabling efficient access to substituted pyridine derivatives. The trimethylsilyl-protected alkyne exhibits excellent bench stability, tolerates a range of functional groups, and facilitates straightforward purification. It functions as a key intermediate in the synthesis of conjugated heterocycles and bioactive scaffolds via Sonogashira or copper-catalyzed couplings.

Synthesis

  • Route1
    • null|null
      109-04-6
    • null|null
      1066-54-2
    • ~99%
    • In-stock
      2-((Trimethylsilyl)ethynyl)pyridine|CS-W017437
      86521-05-3

    References

    • Synthesis, , # 4 p. 312 - 314
  • Route2
    • null|null
      109-09-1
    • null|null
      1066-54-2
    • ~80%
    • In-stock
      2-((Trimethylsilyl)ethynyl)pyridine|CS-W017437
      86521-05-3

    References

    • Chemistry Letters, , vol. 40, # 9 p. 925 - 927
  • Route3
    • null|null
      109-04-6
    • null|null
      1066-54-2
    • ~73%
    • In-stock
      1,4-Bis(trimethylsilyl)buta-1,3-diyne|CS-W010639
      4526-07-2
    • In-stock
      2-((Trimethylsilyl)ethynyl)pyridine|CS-W017437
      86521-05-3

    References

    • Chemistry - An Asian Journal, , vol. 6, # 10 p. 2816 - 2824

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 : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   12.89
  • LogP   2.3105
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   0

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