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CS-W001157 4
Total: USD 88.00

4-Chloro-3-nitrobenzonitrile

  • CAS No. 939-80-0

  • Cat. No. CS-D1140
  • Purity≥98%
  • MDL No.MFCD00016987

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

4-Chloro-3-nitrobenzonitrile|CS-D1140

Structure of 939-80-0

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General Information

  • CAS No. 939-80-0
  • Cat. No. CS-D1140
  • Purity ≥98%
  • MDL No. MFCD00016987
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₃ClN₂O₂
  • Molecular Weight 182.56
  • Synonym(s) 4-chloro-3-nitro-benzonitril
  • SMILES N#CC1=CC=C(Cl)C([N+]([O-])=O)=C1

Description

4-Chloro-3-nitrobenzonitrile features a trifunctional aromatic core combining electron-withdrawing chlorine, nitro, and nitrile groups. This arrangement enhances reactivity in cross-coupling and nucleophilic substitution processes, enabling efficient access to complex heterocycles and functionalized intermediates under standard conditions.

Application

4-Chloro-3-nitrobenzonitrile serves as a versatile building block in medicinal chemistry and agrochemical synthesis, enabling efficient access to substituted benzimidazoles, quinolines, and other heterocyclic scaffolds. The molecule exhibits excellent bench stability and compatibility with standard coupling reactions, including Suzuki-Miyaura and Buchwald-Hartwig protocols. Its orthogonal functional groups—chloro, nitro, and nitrile—allow for sequential transformations with high chemoselectivity, facilitating rapid diversification of core structures in multi-step syntheses.

Synthesis

  • Route1

    References

    • Tidwell; Jones; Geratz; Ohemeng; Cory; Hall Journal of Medicinal Chemistry, 1990 , vol. 33, # 4 p. 1252 - 1257
  • Route2

    References

    • Rao, C. Someswara; Rambabu, M.; Srinivasan, P. S. Synthetic Communications, 1989 , vol. 19, # 7,8 p. 1431 - 1436
  • Route3
    • null|null
      59670-78-9
    • ~88%
    • In-stock
      4-Chloro-3-nitrobenzonitrile|CS-D1140
      939-80-0
    • N,N-Dimethyl-N'-phenylcarbamimidic chloride|CS-0300177
      7684-30-2

    References

    • Kokel, Bruno; Menichi, Gabriel; Hubert-Habart, Michel Synthesis, 1985 , # 2 p. 201 - 202

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   66.93
  • LogP   2.11988
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   1

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