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CS-W001157 4
Total: USD 88.00

2-Propenoic acid, 3-cyclohexyl-, (2E)-

  • CAS No. 56453-86-2

  • Cat. No. CS-0031387
  • Purity≥96%
  • MDL No.MFCD03002774

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

2-Propenoic acid, 3-cyclohexyl-, (2E)-|CS-0031387

Structure of 56453-86-2

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General Information

  • CAS No. 56453-86-2
  • Cat. No. CS-0031387
  • Purity ≥96%
  • MDL No. MFCD03002774
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₄O₂
  • Molecular Weight 154.21
  • Synonym(s) NSC 147133; (2E)-3-CYCLOHEXYLPROP-2-ENOIC ACID
  • SMILES O=C(/C=C/C1CCCCC1)O

Description

(E)-3-Cyclohexylacrylic acid is a sterically defined, bench-stable α,β-unsaturated carboxylic acid featuring a conjugated trans double bond. This configuration enhances its utility in Michael additions and Diels-Alder reactions, where geometric control is critical. The cyclohexyl group imparts hydrophobic character and conformational rigidity, enabling precise spatial positioning in synthetic intermediates. Its moisture-tolerant stability simplifies handling under standard laboratory conditions.

Application

(E)-3-Cyclohexylacrylic acid serves as a versatile building block for synthesizing α,β-unsaturated carboxylic acids and their derivatives. Its conjugated double bond enables reliable Michael additions, Diels–Alder reactions, and palladium-catalyzed couplings. The cyclohexyl group imparts steric bulk and lipophilicity, enhancing metabolic stability in bioactive molecule design. Bench-stable and readily purified by recrystallization, it functions effectively in standard organic transformations.

Synthesis

  • Route1
    • (E)-Ethyl 3-cyclohexylacrylate|CS-0733187
      17343-88-3
    • ~91%
    • In-stock
      2-Propenoic acid, 3-cyclohexyl-, (2E)-|CS-0031387
      56453-86-2

    References

    • Alhamadsheh, Mamoun M.; Palaniappan, Nadaraj; DasChouduri, Suparna; Reynolds, Kevin A. Journal of the American Chemical Society, 2007 , vol. 129, # 7 p. 1910 - 1911
  • Route2
    • null|null
      141-82-2
    • null|null
      2043-61-0
    • ~77%
    • In-stock
      2-Propenoic acid, 3-cyclohexyl-, (2E)-|CS-0031387
      56453-86-2

    References

    • Smejkal, Tomas; Breit, Bernhard Angewandte Chemie - International Edition, 2008 , vol. 47, # 21 p. 3946 - 3949
  • Route3
    • In-stock
      Dibromoacetic acid|CS-0094762
      631-64-1
    • null|null
      2043-61-0
    • ~74%
    • In-stock
      2-Propenoic acid, 3-cyclohexyl-, (2E)-|CS-0031387
      56453-86-2

    References

    • Concellon, Jose M.; Concellon, Carmen Journal of Organic Chemistry, 2006 , vol. 71, # 4 p. 1728 - 1731

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   2.2075
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   2

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