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CS-W001157 4
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3-(1-Pyrazolyl)aniline

  • CAS No. 184097-88-9

  • Cat. No. CS-0156890
  • Purity≥98%
  • MDL No.MFCD08059554

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

3-(1-Pyrazolyl)aniline|CS-0156890

Structure of 184097-88-9

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General Information

  • CAS No. 184097-88-9
  • Cat. No. CS-0156890
  • Purity ≥98%
  • MDL No. MFCD08059554
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₉N₃
  • Molecular Weight 159.19
  • Synonym(s) 3-(1H-pyrazol-1-yl)aniline
  • SMILES C1=CC(=CC(=C1)N2C=CC=N2)N

Description

3-(1-Pyrazolyl)aniline features a pyrazole ring directly fused to an aniline scaffold, delivering enhanced electronic coupling and directional reactivity. This heteroaromatic amine integrates readily into C–N coupling reactions and serves as a key building block in the synthesis of bioactive molecules and functional materials.

Application

3-(1-Pyrazolyl)aniline serves as a versatile building block in medicinal chemistry, enabling the construction of biologically active heterocyclic scaffolds. Its pyrazole and aniline moieties offer orthogonal reactivity for late-stage functionalization, while the molecule exhibits good bench stability and facilitates straightforward purification. The compound functions effectively in Pd-catalyzed coupling reactions and serves as a key intermediate in the synthesis of kinase inhibitors and other targeted therapeutics.

Synthesis

  • Route1
    • 1-(3-Nitrophenyl)-1H-pyrazole|CS-0450420
      25688-18-0
    • ~92%
    • In-stock
      3-(1-Pyrazolyl)aniline|CS-0156890
      184097-88-9

    References

    • BRISTOL-MYERS SQUIBB COMPANY Patent: WO2003/90912 A1, 2003 ; Location in patent: Page/Page column 86 ; WO 03/090912 A1
  • Route2

    References

    • Bioorganic and Medicinal Chemistry Letters, , vol. 18, # 2 p. 576 - 585
  • Route3

    References

    • Tetrahedron, , vol. 57, # 20 p. 4397 - 4403

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS08
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H304
Precautionary Statements : P331-P405-P501

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Computational Chemistry Data

  • TPSA   43.84
  • LogP   1.4545
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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