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CS-W001157 4
Total: USD 88.00

2-(Diphenylphosphino)aniline

  • CAS No. 65423-44-1

  • Cat. No. CS-0199200
  • Molecule weight277.30
  • Purity≥95%
  • MDL No.None

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

2-(Diphenylphosphino)aniline|CS-0199200

Structure of 65423-44-1

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General Information

  • CAS No. 65423-44-1
  • Cat. No. CS-0199200
  • Purity ≥95%
  • MDL No. None
  • Storage 4°C, protect from light, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₈H₁₆NP
  • Molecular Weight 277.30
  • Synonym(s) o-(Diphenylphosphino)aniline
  • SMILES C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3N

Description

2-(Diphenylphosphino)aniline features a diphenylphosphino group directly attached to an aniline scaffold, delivering a robust, electron-rich phosphine ligand. This structure enables efficient coordination in palladium-catalyzed cross-coupling reactions. The ortho-amine functionality enhances metal binding and offers potential for modular derivatization. Bench-stable under standard conditions, it serves as a reliable building block in catalytic system design.

Application

2-(Diphenylphosphino)aniline serves as a versatile phosphine ligand in transition metal catalysis, enabling efficient cross-coupling reactions such as Suzuki-Miyaura and Heck transformations. Its ortho-phosphinoaniline structure provides strong coordination to palladium and nickel centers, enhancing catalyst stability and turnover. The molecule exhibits good bench stability and facilitates purification via standard chromatographic methods, making it well-suited for scalable synthetic applications in medicinal chemistry and materials science.

Synthesis

  • Route1
    • In-stock
      2-Iodoaniline|CS-W007318
      615-43-0
    • null|null
      829-85-6
    • ~86%
    • In-stock
      2-(Diphenylphosphino)aniline|CS-0199200
      65423-44-1

    References

    • Xue, Mei; Li, Jiayun; Peng, Jiajian; Bai, Ying; Zhang, Guodong; Xiao, Wenjun; Lai, Guoqiao Applied Organometallic Chemistry, 2014 , vol. 28, # 2 p. 120 - 126
  • Route2
    • null|null
      124843-09-0
    • ~78%
    • In-stock
      2-(Diphenylphosphino)aniline|CS-0199200
      65423-44-1

    References

    • Dai, Xuedong; Wong, Audrey; Virgil, Scott C. Journal of Organic Chemistry, 1998 , vol. 63, # 8 p. 2597 - 2600
  • Route3
    • null|null
      348-54-9
    • null|null
      15475-27-1
    • ~79%
    • In-stock
      2-(Diphenylphosphino)aniline|CS-0199200
      65423-44-1

    References

    • Seipel, Kelsey R.; Platt, Zed H.; Nguyen, Minh; Holland, Andrew W. Journal of Organic Chemistry, 2008 , vol. 73, # 11 p. 4291 - 4294

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-H312-H332
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P501

Quality Control

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Computational Chemistry Data

  • TPSA   26.02
  • LogP   3.027
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   3

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