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CS-W001157 4
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Diethyl 3-oxohexanedioate

  • CAS No. 7149-59-9

  • Cat. No. CS-0331260
  • Purity≥95%
  • MDL No.MFCD00056286

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

Diethyl 3-oxohexanedioate|CS-0331260

Structure of 7149-59-9

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General Information

  • CAS No. 7149-59-9
  • Cat. No. CS-0331260
  • Purity ≥95%
  • MDL No. MFCD00056286
  • Storage RT, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₁₆O₅
  • Molecular Weight 216.23
  • Synonym(s) β-ketoadipic acid diethyl ester
  • SMILES CCOC(=O)CCC(=O)CC(=O)OCC

Description

Diethyl 3-oxohexanedioate features a β-keto ester moiety flanked by two ester groups, enabling facile enolization and nucleophilic participation. This structural motif supports efficient carbon-carbon bond formation in Claisen condensations and Michael additions, making it a key building block for complex heterocycles and polyfunctional intermediates under standard conditions.

Application

Diethyl 3-oxohexanedioate serves as a versatile synthon in carbonyl-based synthesis, enabling efficient construction of substituted cyclohexanones and heterocyclic scaffolds via Claisen condensation and related transformations. Its α,β-unsaturated ketone functionality supports robust Michael additions and aldol reactions, while the diester moiety facilitates sequential functionalization under mild conditions. Bench-stable and readily purified by distillation or chromatography, it functions reliably in multi-step sequences for natural product and pharmaceutical intermediate synthesis.

Synthesis

  • Route1

    References

    • Takeda Pharmaceutical Company Limited Patent: EP1650201 A1, 2006 ; Location in patent: Page/Page column 26-27 ; EP 1650201 A1
  • Route2
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    • ~%
    • In-stock
      Diethyl 3-oxohexanedioate|CS-0331260
      7149-59-9

    References

    • Canadian Journal of Chemistry, , vol. 33, p. 458,463
  • Route3
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      61975-86-8
    • ~%
    • In-stock
      Diethyl 3-oxohexanedioate|CS-0331260
      7149-59-9

    References

    • Journal of Chemical Research, Miniprint, , # 2 p. 324 - 346

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   69.67
  • LogP   0.852
  • H_Acceptors   5
  • H_Donors   0
  • Rotatable_Bonds   7

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