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CS-W001157 4
Total: USD 88.00

5-Bromo-2-phenylpyridine

  • CAS No. 27012-25-5

  • Cat. No. CS-W014673
  • Purity≥98%
  • MDL No.MFCD04114181

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

5-Bromo-2-phenylpyridine|CS-W014673

Structure of 27012-25-5

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General Information

  • CAS No. 27012-25-5
  • Cat. No. CS-W014673
  • Purity ≥98%
  • MDL No. MFCD04114181
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₈BrN
  • Molecular Weight 234.10
  • Synonym(s) 2-Phenyl-5-bromopyridine
  • SMILES BrC1=CN=C(C=C1)C2=CC=CC=C2

Description

5-Bromo-2-phenylpyridine is a bench-stable, electron-deficient heterocycle featuring a bromine substituent at the 5-position and a phenyl group at the 2-position. This structural motif enables direct coupling in palladium-catalyzed cross-coupling reactions, serving as a key scaffold for constructing biaryl architectures in medicinal chemistry and materials science applications.

Application

5-Bromo-2-phenylpyridine serves as a versatile building block in transition-metal-catalyzed cross-coupling reactions, enabling efficient construction of biaryl and heteroaryl architectures. Its bromine substituent facilitates palladium-catalyzed coupling with boronic acids, amines, and organometallic reagents under standard conditions. The phenylpyridine core provides structural rigidity and enhanced electronic properties, making it suitable for applications in pharmaceutical synthesis and materials science. Bench-stable and readily purified by recrystallization, it functions reliably in multi-step synthetic sequences.

Synthesis

  • Route1

    References

    • Beijing Visionox Technology Co., Ltd.; Kunshan Visionox Display Co., Ltd.; Tsinghua University Patent: EP2500343 A1, 2012 ; Location in patent: Page/Page column 11 ;
  • Route2

    References

    • Zhou, Qizhong; Zhang, Bin; Su, Liangjun; Jiang, Tiansheng; Chen, Rener; Du, Tieqi; Ye, Yuyuan; Shen, Jianfen; Dai, Guoliang; Han, Deman; Jiang, Huajiang Tetrahedron, 2013 , vol. 69, # 51 p. 10996 - 11003
  • Route3

    References

    • Rieke, Reuben D.; Kim, Seung-Hoi Tetrahedron Letters, 2011 , vol. 52, # 2 p. 244 - 247

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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