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2,6-Dibromonaphthalene-1,4,5,8-tetracarboxylic dianhydride

  • CAS No. 83204-68-6

  • Cat. No. CS-0110555
  • Purity≥95%
  • MDL No.MFCD00406909

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

2,6-Dibromonaphthalene-1,4,5,8-tetracarboxylic dianhydride|CS-0110555

Structure of 83204-68-6

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General Information

  • CAS No. 83204-68-6
  • Cat. No. CS-0110555
  • Purity ≥95%
  • MDL No. MFCD00406909
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₄H₂Br₂O₆
  • Molecular Weight 425.97
  • Synonym(s) 4,9-Dibromoisochromeno[6,5,4-def]isochromene-1,3,6,8-tetraone
  • SMILES O=C(OC1=O)C2=CC(Br)=C(C(OC3=O)=O)C4=C3C=C(Br)C1=C24

Description

2,6-Dibromonaphthalene-1,4,5,8-tetracarboxylic dianhydride features a rigid, electron-deficient naphthalene core bearing four anhydride groups and two bromine substituents at the 2,6-positions. This configuration enables high thermal stability and facilitates efficient coupling in polyimide synthesis, particularly for advanced materials requiring precise control over electronic properties and processability.

Application

2,6-Dibromonaphthalene-1,4,5,8-tetracarboxylic dianhydride serves as a versatile building block for the synthesis of functionalized polycyclic aromatic systems. Its four anhydride groups enable facile conjugation via amine or alcohol nucleophiles, while the bromine substituents provide orthogonal handles for palladium-catalyzed cross-coupling reactions. The molecule exhibits excellent bench stability and facilitates purification through crystallization, making it well-suited for iterative synthetic sequences in materials science and pharmaceutical intermediate development.

Synthesis

  • Route1

    References

    • Chaignon, Frederique; Falkenstroem, Magnus; Karlsson, Susanne; Blart, Errol; Odobel, Fabrice; Hammarstroem, Leif Chemical Communications, 2007 , # 1 p. 64 - 66
  • Route2

    References

    • NORTHWESTERN UNIVERSITY Patent: WO2007/146250 A2, 2007 ; Location in patent: Page/Page column 23-24 ;
  • Route3
    • In-stock
      Isochromeno[6,5,4-def]isochromene-1,3,6,8-tetraone|CS-W014044
      81-30-1
    • ~%
    • null|null
      943148-61-6
    • In-stock
      2,6-Dibromonaphthalene-1,4,5,8-tetracarboxylic dianhydride|CS-0110555
      83204-68-6

    References

    • BASF SE Patent: US2008/300405 A1, 2008 ; Location in patent: Page/Page column 17-18 ;

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
Precautionary Statements : P264-P280-P302+P352-P362+P364

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Computational Chemistry Data

  • TPSA   94.56
  • LogP   2.1736
  • H_Acceptors   6
  • H_Donors   0
  • Rotatable_Bonds   0

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