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CS-W001157 4
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N-Methyl-[1,1'-biphenyl]-2-amine

  • CAS No. 14925-09-8

  • Cat. No. CS-W019420
  • Molecule weight183.25
  • Purity≥96%
  • MDL No.MFCD00179576

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

N-Methyl-[1,1'-biphenyl]-2-amine|CS-W019420

Structure of 14925-09-8

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General Information

  • CAS No. 14925-09-8
  • Cat. No. CS-W019420
  • Purity ≥96%
  • MDL No. MFCD00179576
  • Storage 4°C, protect from light, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₃N
  • Molecular Weight 183.25
  • Synonym(s) o-(N-Methylamino)biphenyl
  • SMILES CNC1=C(C2=CC=CC=C2)C=CC=C1

Description

N-Methyl-[1,1'-biphenyl]-2-amine features a sterically accessible aniline nitrogen bearing a methyl substituent, enhancing electron density at the ortho position. This configuration supports efficient coupling in transition-metal-catalyzed reactions and provides improved solubility in organic media compared to unsubstituted analogs. The biphenyl scaffold imparts stability and facilitates π-stacking interactions in coordination environments.

Application

N-Methyl-[1,1'-biphenyl]-2-amine serves as a versatile building block in medicinal chemistry and catalytic synthesis, offering enhanced solubility and metabolic stability over parent aniline derivatives. Its ortho-methylated biphenyl core enables efficient transition-metal-catalyzed coupling reactions, while the N-methyl group provides steric and electronic modulation. The compound exhibits good bench stability, facilitates purification via standard chromatographic methods, and functions effectively in the construction of biologically active heterocyclic scaffolds and functionalized arylamines.

Synthesis

  • Route1
    • null|null
      50-00-0
    • null|null
      90-41-5
    • ~44%
    • In-stock
      N-Methyl-[1,1'-biphenyl]-2-amine|CS-W019420
      14925-09-8

    References

    • Sozio, Piera; Marinelli, Lisa; Cacciatore, Ivana; Fontana, Antonella; Tuerkez, Hasan; Giorgioni, Gianfabio; Ambrosini, Dario; Barbato, Francesco; Grumetto, Lucia; Pacella, Stephanie; Cataldi, Amelia; Di Stefano, Antonio Molecules, 2013 , vol. 18, # 9 p. 10747 - 10767
  • Route2
    • Ethyl [1,1'-biphenyl]-2-ylcarbamate|CS-0668840
      6301-18-4
    • ~89%
    • In-stock
      N-Methyl-[1,1'-biphenyl]-2-amine|CS-W019420
      14925-09-8

    References

    • Peters, Jens-Uwe; Galley, Guido; Jacobsen, Helmut; Czech, Christian; David-Pierson, Pascale; Kitas, Eric A.; Ozmen, Laurence Bioorganic and Medicinal Chemistry Letters, 2007 , vol. 17, # 21 p. 5918 - 5923
  • Route3
    • null|null
      108-90-7
    • null|null
      100-61-8
    • ~63%
    • In-stock
      N-Methyl-N-phenylaniline|CS-W017040
      552-82-9
    • In-stock
      N-Methyl-[1,1'-biphenyl]-2-amine|CS-W019420
      14925-09-8

    References

    • Organic Letters, , vol. 14, # 23 p. 5964 - 5967

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

Quality Control

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Computational Chemistry Data

  • TPSA   12.03
  • LogP   3.3953
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   2

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