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CS-W001157 4
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3-(4-Bromophenyl)cyclobutan-1-one

  • CAS No. 254892-91-6

  • Cat. No. CS-0053973
  • Purity≥97%
  • MDL No.MFCD04038979

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

3-(4-Bromophenyl)cyclobutan-1-one|CS-0053973

Structure of 254892-91-6

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General Information

  • CAS No. 254892-91-6
  • Cat. No. CS-0053973
  • Purity ≥97%
  • MDL No. MFCD04038979
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₉BrO
  • Molecular Weight 225.08
  • Synonym(s) 3-(4-Bromophenyl)cyclobutanone
  • SMILES O=C1CC(C2=CC=C(Br)C=C2)C1

Description

3-(4-Bromophenyl)cyclobutan-1-one features a brominated phenyl group attached to a strained cyclobutanone ring, enabling efficient C–C bond formation in transition-metal-catalyzed cross-coupling reactions. The electron-deficient carbonyl and aryl halide functionalities facilitate sequential functionalization, delivering complex architectures with high regiocontrol under standard conditions.

Application

3-(4-Bromophenyl)cyclobutan-1-one serves as a versatile building block for the synthesis of biaryl-containing cyclobutane scaffolds. Its brominated aryl group enables palladium-catalyzed cross-coupling reactions, while the ketone functionality supports nucleophilic additions and condensation processes. The compound exhibits good bench stability and facilitates straightforward purification, making it well-suited for iterative synthetic sequences in medicinal chemistry and process development.

Synthesis

  • Route1
    • null|null
      254892-87-0
    • ~52%
    • In-stock
      3-(4-Bromophenyl)cyclobutan-1-one|CS-0053973
      254892-91-6

    References

    • Malkov, Andrei V.; Friscourt, Frederic; Bell, Mark; Swarbrick, Martin E.; Kocovsky, Pavel Journal of Organic Chemistry, 2008 , vol. 73, # 11 p. 3996 - 4003
  • Route2

    References

    • PFIZER INC.; ASPNES, Gary, Erik; DOW, Robert, Lee; MUNCHHOF, Michael, John Patent: WO2010/86820 A1, 2010 ; Location in patent: Page/Page column 43 ; WO 2010/086820 A1
  • Route3

    References

    • Xu, Hua-Jian; Zhu, Feng-Fei; Shen, Yong-Ya; Wan, Xin; Feng, Yi-Si Tetrahedron, 2012 , vol. 68, # 22 p. 4145 - 4151

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

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Computational Chemistry Data

  • TPSA   17.07
  • LogP   2.8956
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   1

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