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CS-W001157 4
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4,9-Dibromo-2,7-bis(2-octyldodecyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone

  • CAS No. 1100243-35-3

  • Cat. No. CS-0098911
  • Purity≥95%
  • MDL No.MFCD27923035

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

4,9-Dibromo-2,7-bis(2-octyldodecyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone|CS-0098911

Structure of 1100243-35-3

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General Information

  • CAS No. 1100243-35-3
  • Cat. No. CS-0098911
  • Purity ≥95%
  • MDL No. MFCD27923035
  • Storage RT, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅₄H₈₄Br₂N₂O₄
  • Molecular Weight 985.06
  • Synonym(s) 4,9-Dibromo-2,7-bis(2-octyldodecyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone
  • SMILES O=C(N(CC(CCCCCCCC)CCCCCCCCCC)C(C1=C2C3=C(C(N4CC(CCCCCCCC)CCCCCCCCCC)=O)C=C1Br)=O)C2=CC(Br)=C3C4=O

Description

4,9-Dibromo-2,7-bis(2-octyldodecyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone features a rigid, electron-deficient phenanthroline core functionalized with bromine atoms and long alkyl chains. This combination enables robust metal coordination while enhancing solubility in nonpolar media. The molecule serves as a tailored ligand for transition metal complexes in catalytic and materials applications.

Application

4,9-Dibromo-2,7-bis(2-octyldodecyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone serves as a modular ligand scaffold for transition metal-catalyzed cross-coupling reactions, enabling the construction of extended π-conjugated systems. Its brominated positions facilitate Suzuki-Miyaura and Stille coupling, while the bulky 2-octyldodecyl substituents enhance solubility and prevent aggregation in solution-phase synthesis. The tetrone core provides strong electron-withdrawing character and structural rigidity, making it suitable for applications in organic electronics and coordination chemistry.

Synthesis

  • Route1

    References

    • Chen, Zhihua; Zheng, Yan; Yan, He; Facchetti, Antonio Journal of the American Chemical Society, 2009 , vol. 131, p. 8 - 9

Safety Information

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GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H332-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   78.14
  • LogP   16.3858
  • H_Acceptors   6
  • H_Donors   0
  • Rotatable_Bonds   36

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