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CS-W001157 4
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Dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate

  • CAS No. 6289-46-9

  • Cat. No. CS-W012999
  • Purity≥98%
  • MDL No.MFCD00001607

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

Dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate|CS-W012999

Structure of 6289-46-9

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General Information

  • CAS No. 6289-46-9
  • Cat. No. CS-W012999
  • Purity ≥98%
  • MDL No. MFCD00001607
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₁₂O₆
  • Molecular Weight 228.20
  • Synonym(s) Succinylosuccinic Acid Dimethyl Ester; Dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate
  • SMILES COC(=O)C1CC(=O)C(CC1=O)C(=O)OC

Description

Dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate features a rigid cyclohexanedione scaffold with ester-functionalized carbonyl groups, enabling efficient participation in Diels-Alder reactions and serving as a key synthon for bridged heterocycles. This bench-stable reagent integrates readily into complex molecular architectures under mild conditions.

Application

Dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate serves as a versatile diester building block in synthetic organic chemistry, enabling efficient construction of functionalized cyclohexane scaffolds. Its diketone functionality facilitates aldol-type condensations and enolate-based transformations, while the ester groups support standard hydrolysis and derivatization protocols. The compound exhibits good bench stability and is compatible with a range of reaction conditions, making it a practical choice for modular synthesis of complex cyclic architectures.

Synthesis

  • Route1

    References

    • Seebach, Dieter; Hoffmann, Torsten; Kuehnle, Florian N. M.; Kinkel, Joachim N.; Schulte, Michael Helvetica Chimica Acta, 1995 , vol. 78, # 6 p. 1525 - 1540
  • Route2

    References

    • Asian Journal of Chemistry, , vol. 25, # 3 p. 1349 - 1352
  • Route3
    • Methyl 2-bromo-3-oxobutanoate|CS-0199106
      3600-18-8
    • ~%
    • In-stock
      Dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate|CS-W012999
      6289-46-9

    References

    • Asian Journal of Chemistry, , vol. 25, # 3 p. 1349 - 1352

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

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Computational Chemistry Data

  • TPSA   86.74
  • LogP   -0.5032
  • H_Acceptors   6
  • H_Donors   0
  • Rotatable_Bonds   2

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