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CS-W001157 4
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S-tert-Butyl 3-oxothiobutyrate

  • CAS No. 15925-47-0

  • Cat. No. CS-B0729
  • Molecule weight174.26
  • Purity≥97%
  • MDL No.None

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

S-tert-Butyl 3-oxothiobutyrate|CS-B0729

Structure of 15925-47-0

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General Information

  • CAS No. 15925-47-0
  • Cat. No. CS-B0729
  • Purity ≥97%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₁₄O₂S
  • Molecular Weight 174.26
  • Synonym(s) S-TERT-BUTYL ACETOTHIOACETATE
  • SMILES CC(CC(SC(C)(C)C)=O)=O

Description

S-tert-Butyl 3-oxothiobutyrate features a sterically shielded thioester group flanked by a ketone, enabling stable incorporation into complex molecular architectures. This bench-stable reagent facilitates efficient C–S bond formation under mild conditions, particularly valuable in synthetic routes requiring robust, moisture-tolerant thiocarbonyl equivalents.

Application

S-tert-Butyl 3-oxothiobutyrate serves as a versatile building block in synthetic organic chemistry, enabling efficient access to thioester-functionalized intermediates. Its α-keto thioester motif facilitates nucleophilic additions and participates reliably in Michael reactions and Claisen-type condensations. The tert-butyl thioether group enhances stability and simplifies purification, making it well-suited for bench-scale synthesis and downstream functionalization in complex molecule assembly.

Synthesis

  • Route1
    • null|null
      999-90-6
    • ~%
    • In-stock
      S-tert-Butyl 3-oxothiobutyrate|CS-B0729
      15925-47-0

    References

    • Wilson, G. Edwin; Hess, Arye Journal of Organic Chemistry, 1980 , vol. 45, # 14 p. 2766 - 2772
  • Route2
    • null|null
      674-82-8
    • null|null
      75-66-1
    • ~64%
    • In-stock
      S-tert-Butyl 3-oxothiobutyrate|CS-B0729
      15925-47-0

    References

    • Booth, Paul M.; Fox, Christina, M. J.; Ley, Steve V. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1987 , p. 121 - 130
  • Route3
    • In-stock
      2,2,6-Trimethyl-4H-1,3-dioxin-4-one|CS-W016430
      5394-63-8
    • null|null
      75-66-1
    • ~90%
    • In-stock
      S-tert-Butyl 3-oxothiobutyrate|CS-B0729
      15925-47-0

    References

    • Lopez-Alvarado; Avendano; Menendez Synthetic Communications, 1992 , vol. 22, # 16 p. 2329 - 2333

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-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   34.14
  • LogP   2.0238
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   2

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