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CS-W001157 4
Total: USD 88.00

2,4-Dibromo-1-nitrobenzene

  • CAS No. 51686-78-3

  • Cat. No. CS-W002943
  • Purity≥98%
  • MDL No.MFCD02660416

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

2,4-Dibromo-1-nitrobenzene|CS-W002943

Structure of 51686-78-3

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General Information

  • CAS No. 51686-78-3
  • Cat. No. CS-W002943
  • Purity ≥98%
  • MDL No. MFCD02660416
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₃Br₂NO₂
  • Molecular Weight 280.90
  • Synonym(s) 2,4-Dibromo-1-nitro-benzene
  • SMILES O=[N+](C1=CC=C(Br)C=C1Br)[O-]

Description

2,4-Dibromo-1-nitrobenzene features a nitro group at the para position relative to one bromine, with the second bromine at the meta position, creating a highly functionalized aromatic scaffold. This electron-deficient system enables direct coupling in palladium-catalyzed cross-coupling reactions. The molecule exhibits excellent stability under standard conditions and serves as a key intermediate for synthesizing complex heterocycles and advanced materials.

Application

2,4-Dibromo-1-nitrobenzene serves as a versatile building block in cross-coupling chemistry and heterocycle synthesis. The nitro group enables subsequent reduction and functionalization, while the dibromo substitution pattern facilitates sequential Pd-catalyzed coupling reactions. Its bench-stable nature and compatibility with standard reaction conditions make it well-suited for constructing complex aromatic scaffolds in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • ELI LILLY AND COMPANY Patent: WO2004/14900 A1, 2004 ; Location in patent: Page 24; 57-58 ; WO 2004/014900 A1
  • Route2

    References

    • Aridoss, Gopalakrishnan; Laali, Kenneth K. Journal of Organic Chemistry, 2011 , vol. 76, # 19 p. 8088 - 8094
  • Route3

    References

    • Holleman Recueil des Travaux Chimiques des Pays-Bas, 1906 , vol. 25, p. 202 Recueil des Travaux Chimiques des Pays-Bas, 1908 , vol. 27, p. 151,159

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-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   43.14
  • LogP   3.1198
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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