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1,3-Dibromo-2-nitrobenzene

  • CAS No. 13402-32-9

  • Cat. No. CS-0097947
  • Molecule weight280.90
  • Purity≥98%
  • MDL No.MFCD09998726

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

1,3-Dibromo-2-nitrobenzene|CS-0097947

Structure of 13402-32-9

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General Information

  • CAS No. 13402-32-9
  • Cat. No. CS-0097947
  • Purity ≥98%
  • MDL No. MFCD09998726
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₃Br₂NO₂
  • Molecular Weight 280.90
  • Synonym(s) 2,6-Dibromonitrobenzene
  • SMILES O=[N+]([O-])C1=C(C=CC=C1Br)Br

Description

1,3-Dibromo-2-nitrobenzene is a bifunctional aromatic compound featuring bromine substituents at the 1 and 3 positions flanking a nitro group at the 2 position. This electron-deficient scaffold enables direct coupling in palladium-catalyzed cross-coupling reactions, offering high regiochemical control. The molecule exhibits excellent stability under standard bench conditions and serves as a key building block for complex heterocyclic systems and functionalized aryl materials.

Application

1,3-Dibromo-2-nitrobenzene serves as a versatile building block in synthetic organic chemistry, enabling regioselective functionalization via palladium-catalyzed cross-coupling reactions. The ortho-dibromo substitution pattern facilitates sequential coupling processes, while the nitro group provides a robust handle for further transformation, including reduction to an amine or use in nitro-Mannich reactions. Its bench-stable crystalline form and compatibility with standard reaction conditions make it ideal for constructing complex aromatic scaffolds in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • Morrison, Matthew D.; Hanthorn, Jason J.; Pratt, Derek A. Organic Letters, 2009 , vol. 11, # 5 p. 1051 - 1054
  • Route2
    • null|null
      45739-16-0
    • ~85%
    • In-stock
      1,3-Dibromo-2-nitrobenzene|CS-0097947
      13402-32-9

    References

    • Shen, Dong; Diele, Siegmar; Pelzl, Gerhard; Wirth, Ina; Tschierske, Carsten Journal of Materials Chemistry, 1999 , vol. 9, # 3 p. 661 - 672
  • Route3

    References

    • Gazzetta Chimica Italiana, , vol. 4, p. 341 Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften, , p. 317 Recueil des Travaux Chimiques des Pays-Bas, , vol. 25, p. 202 Recueil des Travaux Chimiques des Pays-Bas, , 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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