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CS-W001157 4
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5-Bromoacenaphthenequinone

  • CAS No. 26254-35-3

  • Cat. No. CS-0187764
  • Purity≥95%
  • MDL No.MFCD18448738

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

5-Bromoacenaphthenequinone|CS-0187764

Structure of 26254-35-3

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General Information

  • CAS No. 26254-35-3
  • Cat. No. CS-0187764
  • Purity ≥95%
  • MDL No. MFCD18448738
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₅BrO₂
  • Molecular Weight 261.07
  • Synonym(s) 1,2-Acenaphthylenedione, 5-bromo-
  • SMILES O=C1C(C2=C3C1=CC=CC3=C(Br)C=C2)=O

Description

5-Bromoacenaphthenequinone features a bromine substituent at the 5-position of the acenaphthenequinone scaffold, enhancing its reactivity in cross-coupling processes. This electron-deficient quinone integrates readily into synthetic pathways requiring halogenated aromatic intermediates. The molecule exhibits bench-stable handling characteristics and maintains structural integrity under standard reaction conditions.

Application

5-Bromoacenaphthenequinone serves as a versatile building block in synthetic organic chemistry, enabling palladium-catalyzed cross-coupling reactions due to its well-defined bromine functionality. The acenaphthenequinone core provides a rigid, electron-deficient aromatic system that facilitates Diels-Alder cycloadditions and nucleophilic substitutions. Its bench-stable crystalline form simplifies handling and purification, making it suitable for iterative synthesis of complex polycyclic scaffolds and functionalized heterocycles in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • Zhang, Hua; Fan, Jiangli; Wang, Jingyun; Dou, Bairui; Zhou, Fan; Cao, Jianfang; Qu, Junle; Cao, Zhi; Zhao, Weijie; Peng, Xiaojun Journal of the American Chemical Society, 2013 , vol. 135, # 46 p. 17469 - 17475
  • Route2

    References

    • Patel, Vijay H.; Patel, Manish P.; Patel, Ranjan G. Heterocyclic Communications, 2001 , vol. 7, # 6 p. 599 - 606
  • Route3
    • 5-Bromoacenaphthylen-1(2H)-one|CS-0652543
      34825-01-9
    • ~91%
    • In-stock
      5-Bromoacenaphthenequinone|CS-0187764
      26254-35-3

    References

    • Tatsugi, Jiro; Okumura, Shigeo; Izawa, Yasuji Bulletin of the Chemical Society of Japan, 1986 , vol. 59, p. 3311 - 3313

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-P280-P302+P352

Quality Control

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Computational Chemistry Data

  • TPSA   34.14
  • LogP   2.9813
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   0

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