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CS-W001157 4
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2-Nitrobenzonitrile

  • CAS No. 612-24-8

  • Cat. No. CS-W016340
  • Purity≥98%
  • MDL No.MFCD00007044

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

2-Nitrobenzonitrile|CS-W016340

Structure of 612-24-8

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General Information

  • CAS No. 612-24-8
  • Cat. No. CS-W016340
  • Purity ≥98%
  • MDL No. MFCD00007044
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₄N₂O₂
  • Molecular Weight 148.12
  • Synonym(s) o-Nitrobenzonitrile; 2-Nitrobenzonitrile
  • SMILES N#CC1=CC=CC=C1[N+]([O-])=O

Description

2-Nitrobenzonitrile features a dual functional group array with a nitro group ortho to a nitrile moiety, enabling strategic integration into cross-coupling and electrophilic substitution cascades. This electron-deficient aromatic scaffold supports efficient derivatization under mild conditions, delivering high-yielding access to complex heterocyclic systems in synthetic methodology development.

Application

2-Nitrobenzonitrile serves as a versatile building block in synthetic organic chemistry, enabling efficient access to substituted benzimidazoles and other heterocyclic scaffolds via cyclization protocols. Its dual electron-withdrawing functionality—nitro and cyano groups—facilitates nucleophilic aromatic substitution and directs regioselective functionalization. The compound exhibits excellent bench stability and is readily purified by recrystallization, making it well-suited for large-scale synthesis and process development in medicinal chemistry workflows.

Synthesis

  • Route1
    • null|null
      3717-25-7
    • ~99%
    • In-stock
      2-Nitrobenzonitrile|CS-W016340
      612-24-8

    References

    • Coskun, Necdet Synthetic Communications, 2004 , vol. 34, # 9 p. 1625 - 1630
  • Route2

    References

    • Dornan, Laura M.; Cao, Qun; Flanagan, James C.A.; Crawford, James J.; Cook, Matthew J.; Muldoon, Mark J. Chemical Communications, 2013 , vol. 49, # 54 p. 6030 - 6032
  • Route3

    References

    • McKillop, Alexander; Tarbin, Jonathan A. Tetrahedron, 1987 , vol. 43, # 8 p. 1753 - 1758

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+H332
Precautionary Statements : P261-P264-P270-P271-P304+P340-P330-P501

Quality Control

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Computational Chemistry Data

  • TPSA   66.93
  • LogP   1.46648
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   1

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