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CS-W001157 4
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6,7-Dichloro-3,4-dihydronaphthalen-1(2H)-one

  • CAS No. 25095-57-2

  • Cat. No. CS-0137709
  • Purity≥98%
  • MDL No.MFCD08234367

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

6,7-Dichloro-3,4-dihydronaphthalen-1(2H)-one|CS-0137709

Structure of 25095-57-2

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General Information

  • CAS No. 25095-57-2
  • Cat. No. CS-0137709
  • Purity ≥98%
  • MDL No. MFCD08234367
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₈Cl₂O
  • Molecular Weight 215.08
  • Synonym(s) 6,7-Dichloro-1-tetralone
  • SMILES O=C1CCCC2=C1C=C(Cl)C(Cl)=C2

Description

6,7-Dichloro-3,4-dihydronaphthalen-1(2H)-one is a chlorinated dihydronaphthalenone scaffold featuring two chlorine substituents at the 6 and 7 positions. This electron-deficient ring system offers enhanced stability and reactivity for use in transition-metal-catalyzed coupling reactions. The carbonyl group at position 1 enables direct functionalization, while the fused bicyclic core provides rigidity ideal for molecular scaffold design in medicinal chemistry and synthetic intermediates.

Application

6,7-Dichloro-3,4-dihydronaphthalen-1(2H)-one serves as a versatile building block in medicinal chemistry, enabling the synthesis of polycyclic scaffolds through standard electrophilic substitution and transition-metal-catalyzed coupling reactions. Its fused ring system offers enhanced metabolic stability and defined spatial orientation, while the ketone functionality facilitates downstream functionalization via nucleophilic addition or enolization. Bench-stable and compatible with common protecting group strategies, it functions effectively in multi-step syntheses requiring structural rigidity and predictable reactivity.

Synthesis

  • Route1
    • 4-(3,4-Dichlorophenyl)butanoic acid|CS-0250020
      25157-66-8
    • ~35%
    • In-stock
      6,7-Dichloro-3,4-dihydronaphthalen-1(2H)-one|CS-0137709
      25095-57-2

    References

    • Owton; Brunavs Synthetic Communications, 1991 , vol. 21, # 8-9 p. 981 - 987
  • Route2
    • 4-(3,4-Dichlorophenyl)-4-oxobutanoic acid|CS-0157139
      50597-19-8
    • ~%
    • In-stock
      6,7-Dichloro-3,4-dihydronaphthalen-1(2H)-one|CS-0137709
      25095-57-2

    References

    • PRESIDENT AND FELLOWS OF HARVARD COLLEGE; CHOREV, Michael; AKTAS, Bertal Huseyin; HALPERIN, Jose A.; WAGNER, Gerhard Patent: WO2012/6068 A2, 2012 ;
  • Route3
    • null|null
      95-50-1
    • ~%
    • In-stock
      6,7-Dichloro-3,4-dihydronaphthalen-1(2H)-one|CS-0137709
      25095-57-2

    References

    • PRESIDENT AND FELLOWS OF HARVARD COLLEGE; CHOREV, Michael; AKTAS, Bertal Huseyin; HALPERIN, Jose A.; WAGNER, Gerhard Patent: WO2012/6068 A2, 2012 ;

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-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   17.07
  • LogP   3.5124
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   0

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