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CS-W001157 4
Total: USD 88.00

1-Nitro-3-vinylbenzene

  • CAS No. 586-39-0

  • Cat. No. CS-0158026
  • Purity≥98%
  • MDL No.MFCD00007276

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

1-Nitro-3-vinylbenzene|CS-0158026

Structure of 586-39-0

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General Information

  • CAS No. 586-39-0
  • Cat. No. CS-0158026
  • Purity ≥98%
  • MDL No. MFCD00007276
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₇NO₂
  • Molecular Weight 149.15
  • Synonym(s) 3-Nitrostyrene
  • SMILES C=CC1=CC(=CC=C1)[N+](=O)[O-]

Description

1-Nitro-3-vinylbenzene features a conjugated vinyl group adjacent to a nitro substituent, enabling efficient copolymerization and incorporation into functional polymer backbones. The electron-deficient vinyl moiety facilitates controlled radical polymerization, while the para-nitro group enhances reactivity in cross-coupling transformations. This bifunctional architecture supports precise molecular design in advanced materials synthesis.

Application

1-Nitro-3-vinylbenzene serves as a versatile building block in synthetic organic chemistry, enabling efficient access to substituted aromatic systems via palladium-catalyzed cross-coupling reactions. The vinyl group facilitates conjugation and participates in Diels-Alder cycloadditions, while the nitro functionality offers robust electrophilic character for subsequent transformations. Its bench-stable nature and compatibility with diverse reaction conditions make it well-suited for the construction of functionalized heterocycles and pharmaceutical scaffolds.

Synthesis

  • Route1
    • null|null
      1779-49-3
    • 3-Nitrobenzaldehyde Erlotinib Impurity|CS-0204123
      99-61-6
    • ~88%
    • In-stock
      1-Nitro-3-vinylbenzene|CS-0158026
      586-39-0

    References

    • EP2505198 A1, ; Page/Page column 47 ;
  • Route2
    • null|null
      645-00-1
    • null|null
      2627-95-4
    • ~74%
    • In-stock
      1-Nitro-3-vinylbenzene|CS-0158026
      586-39-0

    References

    • Journal of the American Chemical Society, , vol. 130, # 11 p. 3690 - 3704
  • Route3
    • null|null
      108-05-4
    • 3-Nitrophenyl trifluoromethanesulfonate|CS-0876208
      32578-25-9
    • ~80%
    • In-stock
      1-Nitro-3-vinylbenzene|CS-0158026
      586-39-0

    References

    • Journal of Organic Chemistry, , vol. 57, # 13 p. 3558 - 3563

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

Quality Control

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Computational Chemistry Data

  • TPSA   43.14
  • LogP   2.2378
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   2

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