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CS-W001157 4
Total: USD 88.00

1-Chloro-4-(2-nitrovinyl)benzene

  • CAS No. 706-07-0

  • Cat. No. CS-W017034
  • Purity≥97%
  • MDL No.None

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

1-Chloro-4-(2-nitrovinyl)benzene|CS-W017034

Structure of 706-07-0

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General Information

  • CAS No. 706-07-0
  • Cat. No. CS-W017034
  • Purity ≥97%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₆ClNO₂
  • Molecular Weight 183.59
  • Synonym(s) 1-(4-Chlorophenyl)-2-nitroethene
  • SMILES O=[N+](/C=C/C1=CC=C(Cl)C=C1)[O-]

Description

1-Chloro-4-(2-nitrovinyl)benzene features a conjugated nitrovinyl group attached to a chlorinated aromatic ring, enabling efficient coupling in cross-coupling reactions. The electron-deficient vinyl moiety enhances reactivity toward nucleophiles, while the ortho-chloro substituent provides a handle for further functionalization. This structure supports precise synthetic control in pharmaceutical and materials development.

Application

1-Chloro-4-(2-nitrovinyl)benzene serves as a versatile building block for the synthesis of substituted arylamines and heterocyclic systems. The chloro group enables palladium-catalyzed cross-coupling reactions, while the nitrovinyl moiety offers a platform for sequential reduction and cyclization to access functionalized benzimidazoles and related scaffolds. Its bench-stable nature and compatibility with diverse reaction conditions make it suitable for iterative synthesis in medicinal chemistry and materials science applications.

Synthesis

  • Route1
    • null|null
      75-52-5
    • In-stock
      4-Chlorobenzaldehyde|CS-W008778
      104-88-1
    • ~98%
    • In-stock
      1-Chloro-4-(2-nitrovinyl)benzene|CS-W017034
      706-07-0

    References

    • SUMITOMO CHEMICAL COMPANY, LIMITED Patent: US2011/152572 A1, 2011 ; Location in patent: Page/Page column 4-5 ;
  • Route2

    References

    • Kumar, M. Satish; Rajanna; Reddy, K. Rajendar; Venkateswarlu; Venkanna Synthetic Communications, 2013 , vol. 43, # 19 p. 2672 - 2677
  • Route3
    • null|null
      75-52-5
    • In-stock
      4-Chlorobenzaldehyde|CS-W008778
      104-88-1
    • ~%
    • In-stock
      1-Chloro-4-(2-nitrovinyl)benzene|CS-W017034
      706-07-0
    • null|null
      852159-30-9

    References

    • Journal of the American Chemical Society, , vol. 131, # 32 p. 11478 - 11484

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07,GHS08
Signal Word : Danger
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H334
Precautionary Statements : P261-P264-P270-P284-P304+P340-P330-P501

Quality Control

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Computational Chemistry Data

  • TPSA   43.14
  • LogP   2.5874
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   2

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