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CS-W001157 4
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2-Bromo-2'-nitroacetophenone

  • CAS No. 6851-99-6

  • Cat. No. CS-W002055
  • Molecule weight244.04
  • Purity≥97%
  • MDL No.MFCD00010294

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

2-Bromo-2'-nitroacetophenone|CS-W002055

Structure of 6851-99-6

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General Information

  • CAS No. 6851-99-6
  • Cat. No. CS-W002055
  • Purity ≥97%
  • MDL No. MFCD00010294
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₆BrNO₃
  • Molecular Weight 244.04
  • Synonym(s) 2-bromo-1-(2-nitrophenyl)ethanone
  • SMILES BrCC(=O)c1ccccc1[N+](=O)[O-]

Description

2-Bromo-2'-nitroacetophenone features a bromine atom at the alpha position and a nitro group at the para position relative to the carbonyl, enabling efficient conjugation and electrophilic reactivity. This bench-stable compound integrates readily into C–C bond-forming processes, particularly in cross-coupling and heterocycle synthesis.

Application

2-Bromo-2'-nitroacetophenone serves as a versatile building block in heterocyclic synthesis, enabling efficient access to substituted quinolines and benzimidazoles via cyclization cascades. Its bromo and nitro functionalities provide orthogonal reactivity for palladium-catalyzed coupling and selective reduction, respectively. The compound exhibits good bench stability and facilitates straightforward purification, making it well-suited for iterative synthetic sequences in medicinal chemistry and process development.

Synthesis

  • Route1

    References

    • Wierenga, Wendell; Harrison, Allen W.; Evans, Bruce R.; Chidester, Connie G. Journal of Organic Chemistry, 1984 , vol. 49, # 3 p. 438 - 442
  • Route2
    • In-stock
      1-(2-Nitrophenyl)ethanone|CS-W017892
      577-59-3
    • ~65%
    • null|null
      35928-59-7
    • In-stock
      2-Bromo-2'-nitroacetophenone|CS-W002055
      6851-99-6

    References

    • Canadian Journal of Chemistry, , vol. 61, p. 400 - 410
  • Route3

    References

    • Canadian Journal of Chemistry, , vol. 61, p. 400 - 410

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05
Signal Word : Danger
UN#: 3261
Class : 8
Packing Group : Ⅱ
Hazard Statements : H314
Precautionary Statements : P260-P264-P280-P301+P330+P331-P304+P340-P363-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   60.21
  • LogP   2.1724
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   3

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