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CS-W001157 4
Total: USD 88.00

cis-Diethyl cyclopropane-1,2-dicarboxylate

  • CAS No. 710-43-0

  • Cat. No. CS-0151916
  • Purity≥95%
  • MDL No.MFCD14525685

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

cis-Diethyl cyclopropane-1,2-dicarboxylate|CS-0151916

Structure of 710-43-0

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General Information

  • CAS No. 710-43-0
  • Cat. No. CS-0151916
  • Purity ≥95%
  • MDL No. MFCD14525685
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₄O₄
  • Molecular Weight None
  • Synonym(s) Diethyl cis-cyclopropane-1,2-dicarboxylate
  • SMILES CCOC(=O)[C@H]1C[C@H]1C(=O)OCC

Description

cis-Diethyl cyclopropane-1,2-dicarboxylate features a rigid, strained cyclopropane ring with adjacent ester groups, enabling precise stereochemical control in cycloaddition reactions. The cis configuration imparts defined spatial orientation, facilitating its use in asymmetric synthesis and natural product derivatization. This bench-stable compound integrates readily into complex molecular architectures under standard conditions.

Application

cis-Diethyl cyclopropane-1,2-dicarboxylate serves as a versatile chiral building block in synthetic organic chemistry, enabling stereoselective transformations via its strained cyclopropyl ring. The molecule facilitates efficient ring-opening reactions and functions as a key intermediate in the synthesis of bioactive heterocycles and natural product analogs. Its bench-stable nature and compatibility with common functional groups support reliable handling and purification in multi-step sequences.

Synthesis

  • Route1
    • null|null
      105-39-5
    • null|null
      140-88-5
    • ~4%
    • In-stock
      cis-Diethyl cyclopropane-1,2-dicarboxylate|CS-0151916
      710-43-0
    • In-stock
      trans-Diethyl cyclopropane-1,2-dicarboxylate|CS-W016909
      3999-55-1

    References

    • Tetrahedron, , vol. 50, # 35 p. 10431 - 10442
  • Route2
    • null|null
      623-73-4
    • null|null
      140-88-5
    • ~%
    • Diethyl (1S,2S)-cyclopropane-1,2-dicarboxylate|CS-0319208
      889461-57-8
    • In-stock
      cis-Diethyl cyclopropane-1,2-dicarboxylate|CS-0151916
      710-43-0
    • null|null
      889461-58-9

    References

    • Journal of the American Chemical Society, , vol. 129, # 40 p. 12074 - 12075
  • Route3
    • null|null
      105-39-5
    • null|null
      140-88-5
    • ~%
    • In-stock
      cis-Diethyl cyclopropane-1,2-dicarboxylate|CS-0151916
      710-43-0

    References

    • Journal of Organic Chemistry, , vol. 32, p. 3351 - 3355

Safety Information

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GHS Pictogram : N/A
GHS No : N/A
Signal Word : N/A
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : N/A
Precautionary Statements : N/A

Quality Control

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Computational Chemistry Data

  • TPSA   52.6
  • LogP   0.7487
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   4

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