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CS-W001157 4
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1-((tert-Butyldimethylsilyl)oxy)propan-2-one

  • CAS No. 74685-00-0

  • Cat. No. CS-0112903
  • Purity≥96%
  • MDL No.MFCD01321330

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

1-((tert-Butyldimethylsilyl)oxy)propan-2-one|CS-0112903

Structure of 74685-00-0

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General Information

  • CAS No. 74685-00-0
  • Cat. No. CS-0112903
  • Purity ≥96%
  • MDL No. MFCD01321330
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₂₀O₂Si
  • Molecular Weight 188.34
  • Synonym(s) 1-{[tert-butyl(dimethyl)silyl]oxy}propan-2-one
  • SMILES CC(CO[Si](C)(C(C)(C)C)C)=O

Description

This silyl ether derivative features a protected tertiary alcohol moiety, enabling stable storage and selective deprotection under mild conditions. The tert-butyldimethylsilyl group enhances solubility in organic media while shielding the hydroxyl function during synthetic manipulations. Ideal for use in complex molecule assembly where orthogonal protection is required.

Application

1-((tert-Butyldimethylsilyl)oxy)propan-2-one serves as a stable, bench-friendly silyl ether protecting group for diol and polyol intermediates in complex molecule synthesis. Its robustness under a wide range of reaction conditions enables selective protection of hydroxyl functionalities, particularly in carbohydrate chemistry and natural product derivatization. The silyl group facilitates clean deprotection with fluoride sources, offering high chemoselectivity and ease of purification in multi-step sequences.

Synthesis

  • Route1
    • null|null
      18162-48-6
    • In-stock
      Hydroxyacetone|CS-0017823
      116-09-6
    • ~96%
    • In-stock
      1-((tert-Butyldimethylsilyl)oxy)propan-2-one|CS-0112903
      74685-00-0

    References

    • Baldwin, Ian R.; Whitby, Richard J. Chemical Communications, 2003 , # 22 p. 2786 - 2787
  • Route2
    • null|null
      96042-30-7
    • In-stock
      Hydroxyacetone|CS-0017823
      116-09-6
    • ~76%
    • In-stock
      1-((tert-Butyldimethylsilyl)oxy)propan-2-one|CS-0112903
      74685-00-0

    References

    • Caldwell, Richard D.; GUCKIAN, Kevin M.; KUMARA VEL, Gnanasambandam; LEE, Wen-Cherng; LIN, Edward Yin-Shiang; LlU, Xiaogao; MA, Bin; SCOTT, Daniel M.; SHl, Zhan; THOMAS, Jermaine; TAVERAS, Arthur G.; ZHENG, Guo Zhu Patent: US2014/100195 A1, 2014 ; Location in patent: Page/Page column ;
  • Route3
    • null|null
      111160-83-9
    • ~76%
    • In-stock
      1-((tert-Butyldimethylsilyl)oxy)propan-2-one|CS-0112903
      74685-00-0

    References

    • O'Brien, Matthew; Baxendale, Ian R.; Ley, Steven V. Organic Letters, 2010 , vol. 12, # 7 p. 1596 - 1598

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   26.3
  • LogP   2.5972
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   3

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