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CS-W001157 4
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2-Methoxycyclohexa-2,5-diene-1,4-dione

  • CAS No. 2880-58-2

  • Cat. No. CS-W016513
  • Molecule weight138.12
  • Purity≥97%
  • MDL No.MFCD00144755

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

2-Methoxycyclohexa-2,5-diene-1,4-dione|CS-W016513

Structure of 2880-58-2

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General Information

  • CAS No. 2880-58-2
  • Cat. No. CS-W016513
  • Purity ≥97%
  • MDL No. MFCD00144755
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₆O₃
  • Molecular Weight 138.12
  • Synonym(s) Methoxy-p-quinone
  • SMILES COC1=CC(=O)C=CC1=O

Description

2-Methoxycyclohexa-2,5-diene-1,4-dione features a conjugated diketone core with a methoxy substituent that enhances solubility and modulates electronic properties. This electron-deficient dienone serves as a key building block in synthetic organic chemistry, particularly for Diels-Alder reactions and heterocycle synthesis under standard conditions.

Application

2-Methoxycyclohexa-2,5-diene-1,4-dione serves as a stable, bench-accessible dienone building block for Diels-Alder reactions and heterocycle synthesis. Its conjugated enone system enables predictable cycloaddition with dienophiles, while the methoxy group enhances solubility and modulates reactivity. The compound exhibits excellent functional group tolerance and facilitates straightforward purification, making it a reliable intermediate in synthetic routes to complex carbocyclic and heterocyclic frameworks.

Synthesis

  • Route1

    References

    • Iwasa, Seiji; Fakhruddin, Ahmad; Widagdo, Herman Setyo; Nishiyama, Hisao Advanced Synthesis and Catalysis, 2005 , vol. 347, # 4 p. 517 - 520
  • Route2
    • Guaiacol Guaifenesin Impurity|CS-0229801
      90-05-1
    • ~92%
    • In-stock
      2-Methoxycyclohexa-2,5-diene-1,4-dione|CS-W016513
      2880-58-2

    References

    • Gaudemer, A.; Nguyen-Van-Duong, K.; Shahkarami, N.; Achi, S. S.; Frostin-Rio, M.; Pujol, D. Tetrahedron, 1985 , vol. 41, # 19 p. 4095 - 4106
  • Route3

    References

    • Deya, Pedro M.; Dopico, Mercedes; Raso, Angel Garcia; Morey, Jeronimo; Saa, Jose M. Tetrahedron, 1987 , vol. 43, # 15 p. 3523 - 3532

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-H335
Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P362-P501

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Computational Chemistry Data

  • TPSA   43.37
  • LogP   0.2247
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   1

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