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CS-W001157 4
Total: USD 88.00

2-(Tert-butyl)pyridine

  • CAS No. 5944-41-2

  • Cat. No. CS-0358901
  • Purity≥97%
  • MDL No.None

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

2-(Tert-butyl)pyridine|CS-0358901

Structure of 5944-41-2

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General Information

  • CAS No. 5944-41-2
  • Cat. No. CS-0358901
  • Purity ≥97%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₃N
  • Molecular Weight 135.21
  • Synonym(s) 2-tert-Butylpyridine
  • SMILES CC(C)(C)C1=CC=CC=N1

Description

2-(Tert-butyl)pyridine features a sterically hindered tert-butyl group at the pyridine ring's 2-position, enhancing its stability and modulating electronic properties. This substitution imparts enhanced solubility in organic media and reduces basicity compared to unsubstituted pyridine. The molecule serves as a valuable ligand in transition metal catalysis, particularly in palladium-catalyzed cross-coupling reactions where steric bulk prevents catalyst deactivation. Its bench-stable nature facilitates handling under standard laboratory conditions.

Application

2-(Tert-butyl)pyridine serves as a versatile building block in synthetic organic chemistry, offering enhanced steric shielding and improved stability due to the bulky tert-butyl group. It functions as a directing group in transition-metal-catalyzed C–H functionalization and enables selective substitution at the ortho position. The compound exhibits excellent bench stability, facilitates straightforward purification, and demonstrates broad compatibility with common reaction conditions, making it a practical choice for constructing complex heterocyclic scaffolds and pharmaceutical intermediates.

Synthesis

  • Route1
    • In-stock
      2-Isopropylpyridine|CS-W019396
      644-98-4
    • null|null
      74-88-4
    • ~87%
    • In-stock
      2-(Tert-butyl)pyridine|CS-0358901
      5944-41-2

    References

    • Pasquinet, Eric; Rocca, Patrick; Marsais, Francis; Godard, Alain; Queguiner, Guy Tetrahedron, 1998 , vol. 54, # 30 p. 8771 - 8782
  • Route2
    • null|null
      38442-51-2
    • null|null
      22581-65-3
    • ~22%
    • In-stock
      4-(tert-Butyl)pyridine|CS-W002002
      3978-81-2
    • In-stock
      2-(Tert-butyl)pyridine|CS-0358901
      5944-41-2
    • 2,4-Di-tert-butylpyridine|CS-0517263
      29939-31-9

    References

    • Russell, Glen A.; Wang, Lijuan; Yao, Ching-Fa Journal of Organic Chemistry, 1995 , vol. 60, # 17 p. 5390 - 5395
  • Route3
    • null|null
      109-04-6
    • null|null
      677-22-5
    • ~66%
    • In-stock
      2-(Tert-butyl)pyridine|CS-0358901
      5944-41-2

    References

    • Bell, Thomas W.; Hu, Lain-Yen; Patel, Sanjay V. Journal of Organic Chemistry, 1987 , vol. 52, # 17 p. 3847 - 3850

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   12.89
  • LogP   2.3791
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   0

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