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CS-W001157 4
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2-Bromo-6-(tert-Butoxy)pyridine

  • CAS No. 949160-14-9

  • Cat. No. CS-0171830
  • Molecule weight230.10
  • Purity≥95%
  • MDL No.None

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

2-Bromo-6-(tert-Butoxy)pyridine|CS-0171830

Structure of 949160-14-9

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General Information

  • CAS No. 949160-14-9
  • Cat. No. CS-0171830
  • Purity ≥95%
  • MDL No. None
  • Storage -20°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₂BrNO
  • Molecular Weight 230.10
  • Synonym(s) 2-Bromo-6-tert-butoxypyridine
  • SMILES CC(C)(C)OC1=CC=CC(=N1)Br

Description

2-Bromo-6-(tert-butoxy)pyridine features a sterically hindered tert-butoxy group that enhances stability and solubility in organic media. This electron-deficient pyridine derivative enables selective coupling reactions under mild conditions, facilitating efficient access to functionalized heterocycles in medicinal chemistry and materials synthesis.

Application

2-Bromo-6-(tert-butoxy)pyridine serves as a versatile building block in heterocyclic synthesis, enabling palladium-catalyzed cross-coupling reactions due to its well-defined reactivity at the bromine site. The tert-butoxy group provides steric protection and enhances solubility, while maintaining compatibility with standard deprotection protocols. Its bench-stable nature and predictable regioselectivity facilitate efficient construction of complex pyridine derivatives in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • Gellrich, Urs; Huang, Jing; Seiche, Wolfgang; Keller, Manfred; Meuwly, Markus; Breit, Bernhard Journal of the American Chemical Society, 2011 , vol. 133, # 4 p. 964 - 975
  • Route2
    • In-stock
      2,6-Dibromopyridine|CS-W008833
      626-05-1
    • null|null
      865-48-5
    • ~98%
    • In-stock
      2-Bromo-6-(tert-Butoxy)pyridine|CS-0171830
      949160-14-9

    References

    • Averin, Alexei D.; Ulanovskaya, Olesya A.; Pleshkova, Nataliya A.; Borisenko, Anatolii A.; Beletskaya, Irina P. Collection of Czechoslovak Chemical Communications, 2007 , vol. 72, # 5-6 p. 785 - 819
  • Route3

    References

    • Curran, Dennis P.; Liu, Hui; Josien, Hubert; Ko, Sung-Bo Tetrahedron, 1996 , vol. 52, # 35 p. 11385 - 11404

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-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   22.12
  • LogP   3.0214
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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