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CS-W001157 4
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5-Methyl-2-phenylpyridine

  • CAS No. 27012-22-2

  • Cat. No. CS-0085797
  • Purity≥98%
  • MDL No.None

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

5-Methyl-2-phenylpyridine|CS-0085797

Structure of 27012-22-2

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General Information

  • CAS No. 27012-22-2
  • Cat. No. CS-0085797
  • Purity ≥98%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₁N
  • Molecular Weight 169.22
  • Synonym(s) 6-Phenyl-3-picoline
  • SMILES CC1=CN=C(C2=CC=CC=C2)C=C1

Description

5-Methyl-2-phenylpyridine is a bench-stable, electron-rich heterocycle featuring a para-substituted phenyl group and a methyl moiety at the 5-position. This configuration enhances π-conjugation and stabilizes coordination to transition metals, enabling its use in catalytic systems requiring robust ligand frameworks.

Application

5-Methyl-2-phenylpyridine serves as a versatile building block in transition-metal-catalyzed cross-coupling reactions, enabling the efficient construction of biaryl and heteroaryl scaffolds. Its electron-rich pyridine core facilitates palladium- and nickel-catalyzed coupling with aryl halides and pseudohalides, while the methyl and phenyl substituents provide steric and electronic modulation. The compound exhibits excellent bench stability, simplifies purification, and functions effectively in both small-molecule synthesis and medicinal chemistry campaigns requiring modular heterocyclic frameworks.

Synthesis

  • Route1

    References

    • Liu, Chun; Han, Na; Song, Xiaoxiao; Qiu, Jieshan European Journal of Organic Chemistry, 2010 , # 29 p. 5548 - 5551
  • Route2
    • null|null
      880353-91-3
    • In-stock
      Iodobenzene|CS-W008603
      591-50-4
    • ~82%
    • In-stock
      5-Methyl-2-phenylpyridine|CS-0085797
      27012-22-2

    References

    • Nokami, Toshiki; Tomida, Yutaka; Kamei, Toshiyuki; Itami, Kenichiro; Yoshida, Jun-Ichi Organic Letters, 2006 , vol. 8, # 4 p. 729 - 731
  • Route3

    References

    • Moriuchi, Toshiyuki; Mao, Lisheng; Wu, Hsyueh-Liang; Ohmura, Satoshi D.; Watanabe, Masami; Hirao, Toshikazu Dalton Transactions, 2012 , vol. 41, # 31 p. 9519 - 9525

Safety Information

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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   3.05702
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   1

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