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CS-W001157 4
Total: USD 88.00

5-Bromo-2-ethylpyridine

  • CAS No. 38749-90-5

  • Cat. No. CS-W019941
  • Purity≥97%
  • MDL No.MFCD11226235

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

5-Bromo-2-ethylpyridine|CS-W019941

Structure of 38749-90-5

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General Information

  • CAS No. 38749-90-5
  • Cat. No. CS-W019941
  • Purity ≥97%
  • MDL No. MFCD11226235
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₈BrN
  • Molecular Weight 186.05
  • Synonym(s) 2-Ethyl-5-bromopyridine; Pyridine, 5-bromo-2-ethyl- (9CI)
  • SMILES CCC1=NC=C(Br)C=C1

Description

5-Bromo-2-ethylpyridine features a pyridine core bearing bromine at the 5-position and an ethyl group at the 2-position, creating a sterically accessible site for palladium-catalyzed cross-coupling reactions. The electron-deficient ring enhances reactivity in C–H functionalization, while the bench-stable nature allows handling under standard conditions. This dual-functionalized scaffold integrates readily into complex heterocyclic architectures.

Application

5-Bromo-2-ethylpyridine serves as a versatile building block in medicinal chemistry and catalytic synthesis, enabling palladium-catalyzed cross-coupling reactions due to its well-defined halogen functionality. The ethyl group at the 2-position provides steric and electronic modulation, enhancing regioselectivity in downstream transformations. Its bench-stable nature and compatibility with diverse reaction conditions make it a practical choice for constructing complex heterocyclic scaffolds and API intermediates.

Synthesis

  • Route1

    References

    • Tilley, Jefferson W.; Zawoiski, Sonja Journal of Organic Chemistry, 1988 , vol. 53, # 2 p. 386 - 390
  • Route2
    • In-stock
      5-Bromo-2-iodopyridine|CS-W002668
      223463-13-6
    • null|null
      557-20-0
    • ~%
    • In-stock
      5-Bromo-2-ethylpyridine|CS-W019941
      38749-90-5

    References

    • BOEHRINGER INGELHEIM INTERNATIONAL GMBH; STURINO, Claudio; BEAULIEU, Pierre; DEROY, Patrick; DUPLESSIS, Martin; JAMES, Clint; LACOSTE, Jean-Eric; MINVILLE, Joannie; MORENCY, Louis; MORIN, Sébastien; SIMONEAU, Bruno; TREMBLAY, Martin Patent: WO2013/91096 A1, 2013 ; Location in patent: Page/Page column 93 ;
  • Route3
    • In-stock
      5-Bromo-2-chloropyridine|CS-W002767
      53939-30-3
    • null|null
      557-20-0
    • ~42%
    • In-stock
      5-Bromo-2-ethylpyridine|CS-W019941
      38749-90-5

    References

    • Nara, Susheel J.; Jha, Mukund; Brinkhorst, Johan; Zemanek, Tony J.; Pratt, Derek A. Journal of Organic Chemistry, 2008 , vol. 73, # 23 p. 9326 - 9333

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-H335
Precautionary Statements : P260-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   12.89
  • LogP   2.4065
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   1

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