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CS-W001157 4
Total: USD 88.00

2-tert-Butoxypyridine

  • CAS No. 83766-88-5

  • Cat. No. CS-0028779
  • Purity≥98%
  • MDL No.MFCD00234567

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

2-tert-Butoxypyridine|CS-0028779

Structure of 83766-88-5

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General Information

  • CAS No. 83766-88-5
  • Cat. No. CS-0028779
  • Purity ≥98%
  • MDL No. MFCD00234567
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₃NO
  • Molecular Weight 151.21
  • Synonym(s) 2-(tert-Butoxy)pyridine
  • SMILES CC(C)(C)OC1=NC=CC=C1

Description

2-tert-Butoxypyridine features a sterically hindered tert-butoxy group at the pyridine ring's 2-position, enhancing its stability and resistance to hydrolysis. This electron-donating substituent modulates the ring’s electronic properties, enabling selective functionalization in cross-coupling reactions. The compound exhibits excellent bench stability and compatibility with diverse reaction conditions, facilitating its integration into complex synthetic sequences.

Application

2-tert-Butoxypyridine serves as a versatile building block in synthetic organic chemistry, enabling regioselective functionalization at the pyridine C2 position. Its tert-butyl ether group provides enhanced bench stability and facilitates subsequent deprotection under mild acidic conditions. The molecule exhibits excellent functional group tolerance and functions effectively in palladium-catalyzed cross-coupling reactions, making it valuable for constructing complex heterocyclic scaffolds and advanced intermediates in medicinal chemistry and process development.

Synthesis

  • Route1
    • null|null
      372-48-5
    • In-stock
      Potassium tert-butoxide|CS-0864415
      865-47-4
    • ~80%
    • In-stock
      2-tert-Butoxypyridine|CS-0028779
      83766-88-5

    References

    • Al-Awadi, Nouria; Ballam, John; Hemblade, Paul R.; Taylor, Roger Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1982 , p. 1175 - 1178
  • Route2
    • null|null
      110-86-1
    • ~%
    • null|null
      372-48-5
    • In-stock
      2-tert-Butoxypyridine|CS-0028779
      83766-88-5
    • null|null
      127827-58-1

    References

    • Stavber, Stojan; Zupan, Marko Tetrahedron Letters, 1990 , vol. 31, # 5 p. 775 - 776

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS02
Signal Word : Danger
UN#: 1993
Class : 3
Packing Group : Ⅲ
Hazard Statements : H226-H315-H319-H335
Precautionary Statements : P210-P233-P240-P241-P242-P243-P280-P303+P361+P353-P370+P378-P403+P235-P501

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Computational Chemistry Data

  • TPSA   22.12
  • LogP   2.2589
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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