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CS-W001157 4
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1,10-Phenanthroline-2-carbonitrile

  • CAS No. 1082-19-5

  • Cat. No. CS-0144693
  • Purity≥97%
  • MDL No.MFCD18431788

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

1,10-Phenanthroline-2-carbonitrile|CS-0144693

Structure of 1082-19-5

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General Information

  • CAS No. 1082-19-5
  • Cat. No. CS-0144693
  • Purity ≥97%
  • MDL No. MFCD18431788
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₇N₃
  • Molecular Weight 205.21
  • Synonym(s) 2-cyano-1,10-phenanthroline
  • SMILES N#CC1=NC2=C3N=CC=CC3=CC=C2C=C1

Description

1,10-Phenanthroline-2-carbonitrile features a rigid aromatic scaffold with a strategically positioned nitrile group at the 2-position, enhancing its electron-withdrawing character. This configuration supports strong chelation in transition metal complexes while improving solubility and stability under standard conditions. The compound serves as a tunable ligand for catalytic systems requiring controlled electronic properties.

Application

1,10-Phenanthroline-2-carbonitrile serves as a versatile ligand in transition metal catalysis, enabling efficient cross-coupling and C–H functionalization reactions. Its ortho-cyanopyridine moiety enhances electronic modulation and chelation strength, improving catalyst stability and turnover. The nitrile group provides a handle for further derivatization, while the rigid phenanthroline scaffold ensures robust coordination to metals such as palladium and copper. This compound exhibits excellent bench stability and is readily purified by recrystallization or column chromatography, making it well-suited for reproducible synthetic workflows in medicinal chemistry and materials science applications.

Synthesis

  • Route1
    • null|null
      1891-19-6
    • null|null
      151-50-8
    • ~92%
    • In-stock
      1,10-Phenanthroline-2-carbonitrile|CS-0144693
      1082-19-5

    References

    • Engbersen; Koudijs; Joosten; Van der Plas Journal of Heterocyclic Chemistry, 1986 , vol. 23, # 4 p. 989 - 900
  • Route2

    References

    • Akerboom, Sebastiaan; Van Den Elshout, Jos J. M. H.; Mutikainen, Ilpo; Siegler, Maxime A.; Fu, Wen Tian; Bouwman, Elisabeth European Journal of Inorganic Chemistry, 2013 , # 36 p. 6137 - 6146
  • Route3
    • null|null
      33730-04-0
    • ~55%
    • In-stock
      1,10-Phenanthroline-2-carbonitrile|CS-0144693
      1082-19-5

    References

    • Zhang, Min; Gao, Rong; Hao, Xiang; Sun, Wen-Hua Journal of Organometallic Chemistry, 2008 , vol. 693, # 26 p. 3867 - 3877

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05
Signal Word : Danger
UN#: 1759
Class : 8
Packing Group : Ⅲ
Hazard Statements : H302-H318
Precautionary Statements : P260-P264-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P363-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   49.57
  • LogP   2.65468
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   0

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