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CS-W001157 4
Total: USD 88.00

4-Bromo-2-nitrobenzaldehyde

  • CAS No. 5551-12-2

  • Cat. No. CS-W007379
  • Purity≥96%
  • MDL No.MFCD00463687

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

4-Bromo-2-nitrobenzaldehyde|CS-W007379

Structure of 5551-12-2

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General Information

  • CAS No. 5551-12-2
  • Cat. No. CS-W007379
  • Purity ≥96%
  • MDL No. MFCD00463687
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₄BrNO₃
  • Molecular Weight 230.02
  • Synonym(s) Nifedipine Impurity 20
  • SMILES O=CC1=CC=C(Br)C=C1[N+]([O-])=O

Description

4-Bromo-2-nitrobenzaldehyde features a bromine atom at the para position relative to an electron-deficient aldehyde group, flanked by a nitro group at the ortho position. This combination enhances electrophilicity and enables selective coupling in cross-coupling reactions. The molecule exhibits high stability under standard conditions and integrates readily into complex heterocyclic architectures.

Application

4-Bromo-2-nitrobenzaldehyde serves as a versatile building block in synthetic organic chemistry, enabling the construction of substituted heterocycles and functionalized aromatic systems. Its ortho-nitro and para-bromo substituents provide complementary reactivity for palladium-catalyzed cross-coupling and nitro group reduction, facilitating downstream transformations. The aldehyde functionality supports nucleophilic addition and condensation reactions, while the molecule exhibits good bench stability and ease of purification—making it a practical choice for medicinal chemistry and process development workflows.

Synthesis

  • Route1

    References

    • NOVARTIS VACCINES and DIAGNOSTICS, INC. Patent: WO2007/117607 A2, 2007 ; Location in patent: Page/Page column 333 ;
  • Route2
    • null|null
      135308-80-4
    • ~91%
    • In-stock
      4-Bromo-2-nitrobenzaldehyde|CS-W007379
      5551-12-2

    References

    • Imming; Imhof; Zentgraf Synthetic Communications, 2001 , vol. 31, # 23 p. 3721 - 3727
  • Route3
    • In-stock
      1,4-Dibromo-2-nitrobenzene|CS-W002018
      3460-18-2
    • null|null
      68-12-2
    • ~%
    • In-stock
      4-Bromo-2-nitrobenzaldehyde|CS-W007379
      5551-12-2

    References

    • Chemische Berichte, , vol. 122, p. 1199 - 1202

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07,GHS09
Signal Word : Warning
UN#: 3077
Class : 9
Packing Group : Ⅲ
Hazard Statements : H302-H315-H317-H319-H335-H410
Precautionary Statements : P260-P261-P264-P270-P271-P272-P273-P280-P301+P310-P302+P352-P304+P340-P305+P351+P338-P312-P330-P332+P313-P333+P317-P337+P313-P362+P364-P391-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   60.21
  • LogP   2.1698
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   2

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