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CS-W001157 4
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2-Methoxy-4-nitrobenzonitrile

  • CAS No. 101084-96-2

  • Cat. No. CS-0138989
  • Purity≥95%
  • MDL No.MFCD02093781

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

2-Methoxy-4-nitrobenzonitrile|CS-0138989

Structure of 101084-96-2

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General Information

  • CAS No. 101084-96-2
  • Cat. No. CS-0138989
  • Purity ≥95%
  • MDL No. MFCD02093781
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₆N₂O₃
  • Molecular Weight 178.14
  • Synonym(s) 2-CYANO-5-NITROANISOLE
  • SMILES N#CC1=CC=C([N+]([O-])=O)C=C1OC

Description

2-Methoxy-4-nitrobenzonitrile features a conjugated triad of electron-withdrawing nitrile and nitro groups flanking a methoxy substituent, enabling robust participation in cross-coupling reactions. This ortho-directing motif delivers high regioselectivity in Pd-catalyzed transformations, while the benzonitrile scaffold supports efficient derivatization under standard conditions.

Application

2-Methoxy-4-nitrobenzonitrile serves as a versatile building block in medicinal chemistry and agrochemical synthesis, enabling efficient access to substituted heterocycles via cyclization reactions. Its orthogonal functionality—combining a nitrile, nitro, and methoxy group—permits selective transformations under standard conditions. The compound exhibits good bench stability and facilitates straightforward purification, making it well-suited for multi-step synthetic sequences requiring precise functional group control.

Synthesis

  • Route1

    References

    • Bristol-Myers Squibb Company Patent: US6596747 B2, 2003 ;
  • Route2
    • In-stock
      2-Hydroxy-4-nitrobenzonitrile|CS-0099377
      39835-14-8
    • null|null
      74-88-4
    • ~89%
    • In-stock
      2-Methoxy-4-nitrobenzonitrile|CS-0138989
      101084-96-2

    References

    • Mackman; Katz; Breitenbucher; Hui; Verner; Luong; Liu; Sprengeler Journal of Medicinal Chemistry, 2001 , vol. 44, # 23 p. 3856 - 3871
  • Route3
    • Methyl 6-nitrobenzo[d]isoxazole-3-carboxylate|CS-0103847
      5453-86-1
    • ~%
    • In-stock
      2-Methoxy-4-nitrobenzonitrile|CS-0138989
      101084-96-2

    References

    • Journal of the American Chemical Society, , vol. 74, p. 2226,2235

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-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   76.16
  • LogP   1.47508
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   2

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