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Cyclohex-3-en-1-ol

  • CAS No. 822-66-2

  • Cat. No. CS-0161778
  • Purity≥95%
  • MDL No.MFCD00040176

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

Cyclohex-3-en-1-ol|CS-0161778

Structure of 822-66-2

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General Information

  • CAS No. 822-66-2
  • Cat. No. CS-0161778
  • Purity ≥95%
  • MDL No. MFCD00040176
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₁₀O
  • Molecular Weight 98.14
  • Synonym(s) 3-Cyclohexen-1-ol
  • SMILES OC1CC=CCC1

Description

Cyclohex-3-en-1-ol is a conjugated enol featuring a hydroxyl group at C1 and a double bond between C3 and C4, enabling facile tautomerization to the corresponding carbonyl. This structure supports direct participation in Diels-Alder reactions and electrophilic functionalizations. The compound exhibits enhanced stability under standard conditions due to extended π-conjugation and is compatible with common synthetic workflows.

Application

Cyclohex-3-en-1-ol serves as a versatile intermediate in synthetic organic chemistry, enabling efficient access to functionalized cyclohexane derivatives. Its conjugated enol functionality facilitates electrophilic additions, oxidation reactions, and transition-metal-catalyzed transformations. The molecule exhibits good bench stability and can be readily purified by distillation or chromatography, making it well-suited for scale-up applications in medicinal chemistry and natural product synthesis.

Synthesis

  • Route1
    • Bicyclo[3.1.0]hexane|CS-0876443
      285-58-5
    • ~4%
    • Cyclopent-2-enyl-methanol|CS-0341069
      13668-59-2
    • (1α,2β,5α)-Bicyclo[3.1.0]hexan-2-ol|CS-0927371
      822-58-2
    • (1α,2β,5α)-Bicyclo[3.1.0]hexan-2-ol|CS-0927371
      822-58-2
    • In-stock
      Cyclohex-3-en-1-ol|CS-0161778
      822-66-2

    References

    • Journal of the American Chemical Society, , vol. 129, # 12 p. 3514 - 3515
  • Route2
    • null|null
      1165952-92-0
    • ~81%
    • In-stock
      Cyclohex-3-en-1-ol|CS-0161778
      822-66-2

    References

    • Donohoe, Timothy J.; Mitchell, Lee; Waring, Michael J.; Helliwell, Madeleine; Bell, Andrew; Newcombe, Nicholas J. Organic and Biomolecular Chemistry, 2003 , vol. 1, # 12 p. 2173 - 2186
  • Route3

    References

    • Journal of Organic Chemistry, , vol. 66, # 13 p. 4710 - 4712

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H227-H302-H319-H332-H335
Precautionary Statements : P210-P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362-P370+P378-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   20.23
  • LogP   1.0874
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   0

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