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CS-W001157 4
Total: USD 88.00

2-Hydroxycyclopent-2-en-1-one

  • CAS No. 10493-98-8

  • Cat. No. CS-W019237
  • Purity≥95%
  • MDL No.MFCD16251523

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

2-Hydroxycyclopent-2-en-1-one|CS-W019237

Structure of 10493-98-8

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General Information

  • CAS No. 10493-98-8
  • Cat. No. CS-W019237
  • Purity ≥95%
  • MDL No. MFCD16251523
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₆O₂
  • Molecular Weight 98.10
  • Synonym(s) None
  • SMILES O=C1C(O)=CCC1

Description

2-Hydroxycyclopent-2-en-1-one is a reactive enol tautomer featuring a conjugated carbonyl and hydroxyl group within a strained five-membered ring. This structural motif enables direct participation in electrophilic additions and facilitates rapid cyclization under mild conditions. The compound's inherent instability drives dynamic reactivity, making it valuable for constructing complex heterocycles and natural product intermediates in synthetic organic chemistry workflows.

Application

2-Hydroxycyclopent-2-en-1-one serves as a versatile synthon in organic synthesis, enabling efficient access to substituted cyclopentane derivatives through facile Michael additions and aldol-type condensations. Its enolizable carbonyl and conjugated alkene functionality facilitate diverse transformations under mild conditions, with demonstrated utility in constructing biologically relevant heterocyclic scaffolds. Bench-stable and amenable to straightforward purification, it functions reliably in multi-step sequences requiring functional group tolerance and predictable reactivity.

Synthesis

  • Route1

    References

    • Reile, Indrek; Kalle, Sigrid; Werner, Franz; Jaerving, Ivar; Kudrjashova, Marina; Paju, Anne; Lopp, Margus Tetrahedron, 2014 , vol. 70, # 22 p. 3608 - 3613
  • Route2
    • 6-Bromo-1,4-dioxaspiro[4.4]Nonane|CS-0455907
      82235-82-3
    • ~86%
    • In-stock
      2-Hydroxycyclopent-2-en-1-one|CS-W019237
      10493-98-8

    References

    • Fadel, Antoine; Yefsah, Ramdane; Salauen, Jacques Synthesis, 1987 , # 1 p. 37 - 40
  • Route3
    • null|null
      1056246-36-6
    • ~55%
    • In-stock
      2-Hydroxycyclopent-2-en-1-one|CS-W019237
      10493-98-8

    References

    • Xu, Hanhui; Wolf, Christian Angewandte Chemie - International Edition, 2011 , vol. 50, # 51 p. 12249 - 12252

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   37.3
  • LogP   0.7912
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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