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CS-W001157 4
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2-Methoxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one

  • CAS No. 6500-65-8

  • Cat. No. CS-0069817
  • Purity≥97%
  • MDL No.MFCD07369971

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

2-Methoxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one|CS-0069817

Structure of 6500-65-8

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General Information

  • CAS No. 6500-65-8
  • Cat. No. CS-0069817
  • Purity ≥97%
  • MDL No. MFCD07369971
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₄O₂
  • Molecular Weight 190.24
  • Synonym(s) 2-Methoxy-6,7,8,9-tetrahydro-benzocyclohepten-5-one
  • SMILES O=C1CCCCC2=CC(OC)=CC=C21

Description

2-Methoxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one is a fused polycyclic ketone featuring a tetrahydrobenzannulene core with a methoxy-substituted aromatic ring. This electron-rich scaffold enables direct functionalization at the benzo annulene junction and exhibits enhanced solubility compared to related systems. The carbonyl group serves as a key handle for nucleophilic additions and reductive transformations under mild conditions.

Application

2-Methoxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one serves as a versatile building block for complex polycyclic architectures, enabling efficient access to fused heterocyclic systems via controlled ring closure and functional group manipulation. Its methoxy-substituted ketone functionality offers predictable reactivity in nucleophilic additions and reductions, while the saturated benzoannulene core provides structural rigidity beneficial for scaffold diversification in medicinal chemistry applications. Bench-stable and compatible with standard purification protocols, it functions effectively in multi-step synthesis workflows requiring robust intermediates.

Synthesis

  • Route1
    • 5-(3-Methoxyphenyl)pentanoic acid|CS-0454560
      6500-64-7
    • ~99%
    • In-stock
      2-Methoxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one|CS-0069817
      6500-65-8

    References

    • WO2012/50848 A1, ; Page/Page column 115-116 ;
  • Route2
    • null|null
      21336-18-5
    • ~24%
    • In-stock
      2-Methoxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one|CS-0069817
      6500-65-8

    References

    • US2006/293394 A1, ; Page/Page column 25 ;
  • Route3
    • 2-Methoxy-6,7,8,9-tetrahydro-5h-benzo[7]annulen-5-amine|CS-0750316
      132555-99-8
    • ~78%
    • In-stock
      2-Methoxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one|CS-0069817
      6500-65-8

    References

    • Tetrahedron, , vol. 46, # 19 p. 6869 - 6878

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-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   26.3
  • LogP   2.6043
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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