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3-(3-Bromophenyl)pyridine

  • CAS No. 4422-32-6

  • Cat. No. CS-0168405
  • Purity≥98%
  • MDL No.MFCD16658917

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

3-(3-Bromophenyl)pyridine|CS-0168405

Structure of 4422-32-6

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General Information

  • CAS No. 4422-32-6
  • Cat. No. CS-0168405
  • Purity ≥98%
  • MDL No. MFCD16658917
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₈BrN
  • Molecular Weight 234.09
  • Synonym(s) 3-(m-Bromophenyl)pyridine
  • SMILES BrC1=CC(C2=CC=CN=C2)=CC=C1

Description

3-(3-Bromophenyl)pyridine features a brominated phenyl group attached to a pyridine core, enabling direct functionalization in cross-coupling reactions. This electron-deficient heteroaryl scaffold integrates readily into pharmaceutical intermediates and advanced materials. The bromine moiety offers high reactivity under palladium catalysis, while the pyridine nitrogen provides coordination versatility for metal complexation. Bench-stable and compatible with standard synthetic protocols.

Application

3-(3-Bromophenyl)pyridine serves as a versatile building block in cross-coupling chemistry, enabling efficient construction of biaryl scaffolds via palladium-catalyzed reactions. The bromo group exhibits high reactivity in Suzuki, Stille, and Negishi couplings, while the pyridine nitrogen provides coordination sites for metal catalysts and enhances solubility in organic media. Bench-stable and readily purified by flash chromatography, it functions effectively in the synthesis of pharmaceutical intermediates and functional materials.

Synthesis

  • Route1

    References

    • General Electric Company Patent: US2010/331547 A1, 2010 ; Location in patent: Page/Page column 13 ;
  • Route2

    References

    • Trokowski, Robert; Akine, Shigehisa; Nabeshima, Tatsuya Chemical Communications, 2008 , # 7 p. 889 - 890
  • Route3

    References

    • Blackaby, Wesley Peter; Goodacre, Simon Charles; Hallett, David James; Jennings, Andrew; Lewis, Richard Thomas; Moore, Kevin William; Street, Leslie Joseph Patent: US2003/176449 A1, 2003 ;

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

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Computational Chemistry Data

  • TPSA   12.89
  • LogP   3.5111
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   1

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