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CS-W001157 4
Total: USD 88.00

5,12-Naphthacenequinone

  • CAS No. 1090-13-7

  • Cat. No. CS-0155661
  • Purity≥95%
  • MDL No.MFCD00003701

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

5,12-Naphthacenequinone|CS-0155661

Structure of 1090-13-7

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General Information

  • CAS No. 1090-13-7
  • Cat. No. CS-0155661
  • Purity ≥95%
  • MDL No. MFCD00003701
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₈H₁₀O₂
  • Molecular Weight 258.27
  • Synonym(s) Tetracenequinone
  • SMILES C1=CC2=CC3=C(C=C2C=C1)C(=O)C4=CC=CC=C4C3=O

Description

5,12-Naphthacenequinone is a polycyclic aromatic quinone featuring a rigid, planar core with two carbonyl groups positioned at the 5 and 12 ring junctions. This arrangement imparts strong electron-accepting character, enabling its use in organic semiconductors and redox-active materials. The extended π-system enhances charge delocalization, while the quinone functionality supports reversible reduction under ambient conditions.

Application

5,12-Naphthacenequinone serves as a versatile polycyclic quinone scaffold for organic synthesis, enabling access to extended π-conjugated systems through standard Diels-Alder and cycloaddition reactions. Its robust bench stability and defined regiochemistry facilitate reliable functionalization, making it a practical building block for advanced materials and heterocyclic compound development.

Synthesis

  • Route1
    • null|null
      13209-15-9
    • 1,4-Naphthoquinone Dapoxetine  Impurity|CS-0228897
      130-15-4
    • ~63%
    • In-stock
      5,12-Naphthacenequinone|CS-0155661
      1090-13-7

    References

    • Odom, Susan A.; Parkin, Sean R.; Anthony, John E. Organic Letters, 2003 , vol. 5, # 23 p. 4245 - 4248
  • Route2

    References

    • Nishina, Yuta; Kida, Tatsuya; Ureshino, Tomonari Organic Letters, 2011 , vol. 13, # 15 p. 3960 - 3963
  • Route3

    References

    • Reichwagen, Jens; Hopf, Henning; Del Guerzo, Andre; Desvergne, Jean-Pierre; Bouas-Laurent, Henri Organic Letters, 2004 , vol. 6, # 12 p. 1899 - 1902

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H317-H319
Precautionary Statements : P261-P264-P272-P280-P302+P352-P362+P364-P501

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Computational Chemistry Data

  • TPSA   34.14
  • LogP   3.6152
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   0

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