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CS-W001157 4
Total: USD 88.00

5-Bromo-2-cyclopropylpyridine

  • CAS No. 579475-29-9

  • Cat. No. CS-W022305
  • Purity≥98%
  • MDL No.MFCD12033369

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

5-Bromo-2-cyclopropylpyridine|CS-W022305

Structure of 579475-29-9

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General Information

  • CAS No. 579475-29-9
  • Cat. No. CS-W022305
  • Purity ≥98%
  • MDL No. MFCD12033369
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₈BrN
  • Molecular Weight 198.06
  • Synonym(s) 3-Bromo-6-(cyclopropyl)pyridine
  • SMILES BrC1=CN=C(C2CC2)C=C1

Description

5-Bromo-2-cyclopropylpyridine features a cyclopropyl group at the 2-position and a bromine atom at the 5-position of the pyridine ring, creating a sterically constrained, electron-deficient heteroaryl scaffold. This configuration enables direct coupling in palladium-catalyzed cross-coupling reactions, delivering complex substituted pyridines with high regiocontrol. The molecule exhibits excellent bench stability and compatibility with standard reaction conditions.

Application

5-Bromo-2-cyclopropylpyridine serves as a versatile building block in medicinal chemistry and catalytic cross-coupling reactions. The bromine substituent enables reliable Suzuki, Stille, and Negishi couplings, while the cyclopropyl group imparts metabolic stability and modulates electronic properties. Its bench-stable nature and compatibility with diverse reaction conditions make it well-suited for constructing complex heterocyclic scaffolds in API development.

Synthesis

  • Route1
    • In-stock
      2,5-Dibromopyridine|CS-W001991
      624-28-2
    • null|null
      23719-80-4
    • ~50%
    • In-stock
      5-Bromo-2-cyclopropylpyridine|CS-W022305
      579475-29-9

    References

    • ASTRAZENECA AB Patent: WO2006/65215 A1, 2006 ; Location in patent: Page/Page column 28 ; WO 2006/065215 A1
  • Route2
    • In-stock
      2,5-Dibromopyridine|CS-W001991
      624-28-2
    • null|null
      203861-73-8
    • ~99%
    • In-stock
      5-Bromo-2-cyclopropylpyridine|CS-W022305
      579475-29-9

    References

    • McArthur, Silvia Gatti; Goetschi, Erwin; Palmer, Wylie Solang; Wichmann, Juergen; Woltering, Thomas Johannes Patent: US2006/217387 A1, 2006 ; Location in patent: Page/Page column 27 ; US 20060217387 A1

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-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   12.89
  • LogP   2.7215
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   1

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