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CS-W001157 4
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3-Bromocyclobutanone

  • CAS No. 23761-24-2

  • Cat. No. CS-0040508
  • Purity≥95%
  • MDL No.MFCD20622640

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

3-Bromocyclobutanone|CS-0040508

Structure of 23761-24-2

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General Information

  • CAS No. 23761-24-2
  • Cat. No. CS-0040508
  • Purity ≥95%
  • MDL No. MFCD20622640
  • Storage -20°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₄H₅BrO
  • Molecular Weight 148.99
  • Synonym(s) 3-bromocyclobutan-1-one
  • SMILES O=C1CC(Br)C1

Description

3-Bromocyclobutanone is a strained, reactive ketone featuring a bromine substituent on the cyclobutane ring. This electrophilic functionality enables direct incorporation into C–C bond-forming reactions and facilitates downstream functionalization via nucleophilic displacement or transition-metal-catalyzed coupling. The molecule exhibits enhanced reactivity due to ring strain and adjacent carbonyl polarization.

Application

3-Bromocyclobutanone serves as a versatile synthetic building block for cyclobutane-based scaffolds, enabling direct functionalization at the C3 position. Its electrophilic bromine facilitates nucleophilic substitution and metal-catalyzed coupling reactions, while the ketone group supports enolization, aldol chemistry, and reductive amination. The compound exhibits good bench stability and is compatible with common protecting group strategies, facilitating its use in iterative synthesis of complex cyclic architectures.

Synthesis

  • Route1

    References

    • OSI PHARMACEUTICALS, INC.; APPARI, Rama, Devi; CHEN, Xin; CHILUKURI, Ramesh; CREW, Andrew, P.; DONG, Hanqing; FERRARO, Caterina; FOREMAN, Kenneth; GUPTA, Ramesh, C.; LI, An-hu; SHERMAN, Dan; STOLZ, Kathryn, M.; VOLK, Brian; ZAHLER, Robert Patent: WO2010/141406 A2, 2010 ; Location in patent: Page/Page column 91 ; WO 2010/141406 A2

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
Precautionary Statements : P264-P270-P330-P501

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Computational Chemistry Data

  • TPSA   17.07
  • LogP   1.1128
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   0

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