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CS-W001157 4
Total: USD 88.00

2-Amino-6-methoxybenzonitrile

  • CAS No. 1591-37-3

  • Cat. No. CS-W006615
  • Purity≥97%
  • MDL No.MFCD09745275

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

2-Amino-6-methoxybenzonitrile|CS-W006615

Structure of 1591-37-3

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General Information

  • CAS No. 1591-37-3
  • Cat. No. CS-W006615
  • Purity ≥97%
  • MDL No. MFCD09745275
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₈N₂O
  • Molecular Weight 148.16
  • Synonym(s) 2-AMINO-6-METHOXY BENZONITRILE
  • SMILES COC1=CC=CC(N)=C1C#N

Description

2-Amino-6-methoxybenzonitrile features a strategically positioned amino group and methoxy substituent that enhance electron density and solubility, enabling efficient coupling in transition-metal-catalyzed transformations. The nitrile moiety provides a robust handle for downstream functionalization, while the ortho-amino and para-methoxy arrangement ensures stability under standard bench conditions.

Application

2-Amino-6-methoxybenzonitrile serves as a versatile building block in medicinal chemistry, enabling the synthesis of heterocyclic scaffolds via cyclization reactions. Its ortho-directed reactivity facilitates efficient functionalization, while the amino and nitrile groups offer complementary handles for derivatization. The methoxy substituent enhances solubility and modulates electronic properties, contributing to favorable handling and purification characteristics in multi-step syntheses.

Synthesis

  • Route1
    • 2-Methoxy-6-nitrobenzonitrile|CS-0465390
      38469-85-1
    • ~78%
    • In-stock
      2-Amino-6-methoxybenzonitrile|CS-W006615
      1591-37-3

    References

    • Klaubert, Dieter H.; Sellstedt, John H.; Guinosso, Charles J.; Capetola, Robert J.; Bell, Stanley C. Journal of Medicinal Chemistry, 1981 , vol. 24, # 6 p. 742 - 748
  • Route2
    • In-stock
      2-Amino-6-fluorobenzonitrile|CS-W001178
      77326-36-4
    • null|null
      124-41-4
    • ~61%
    • In-stock
      2-Amino-6-methoxybenzonitrile|CS-W006615
      1591-37-3

    References

    • BASF Aktiengesellschaft Patent: WO2006/56433 A2, 2006 ; Location in patent: Page/Page column 31-32 ;
  • Route3
    • 2,6-Dinitrobenzonitrile|CS-0132605
      35213-00-4
    • ~%
    • In-stock
      2-Amino-6-methoxybenzonitrile|CS-W006615
      1591-37-3

    References

    • Journal of Medicinal Chemistry, , vol. 33, # 1 p. 434 - 444

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

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Computational Chemistry Data

  • TPSA   59.04
  • LogP   1.14908
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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