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CS-W001157 4
Total: USD 88.00

4,4-Dimethyloxazolidin-2-one

  • CAS No. 26654-39-7

  • Cat. No. CS-W011238
  • Purity≥97%
  • MDL No.MFCD04038702

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

4,4-Dimethyloxazolidin-2-one|CS-W011238

Structure of 26654-39-7

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General Information

  • CAS No. 26654-39-7
  • Cat. No. CS-W011238
  • Purity ≥97%
  • MDL No. MFCD04038702
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₉NO₂
  • Molecular Weight 115.13
  • Synonym(s) 4,4-Dimethyl-2-Oxazolidinone
  • SMILES O=C1OCC(C)(C)N1

Description

4,4-Dimethyloxazolidin-2-one is a bench-stable, moisture-tolerant heterocycle featuring a sterically hindered oxazolidinone core. This structure integrates a tertiary carbon adjacent to the carbonyl, enhancing resistance to nucleophilic attack. The compound serves as a robust chiral auxiliary in asymmetric synthesis and delivers high enantioselectivity in conjugate additions. Its stability under standard conditions simplifies handling in process development workflows.

Application

4,4-Dimethyloxazolidin-2-one serves as a robust chiral auxiliary in asymmetric synthesis, enabling high diastereoselective transformations through its stable enolizable carbonyl and defined stereogenic center. Its bench-stable nature and compatibility with common reagents facilitate straightforward functionalization, purification, and subsequent cleavage—making it a reliable choice for constructing complex stereocontrolled intermediates in medicinal chemistry and natural product synthesis.

Synthesis

  • Route1
    • null|null
      543-28-2
    • ~86%
    • In-stock
      4,4-Dimethyloxazolidin-2-one|CS-W011238
      26654-39-7

    References

    • Li, Zigang; Capretto; Rahaman; He, Chuan Angewandte Chemie - International Edition, 2007 , vol. 46, # 27 p. 5184 - 5186
  • Route2
    • null|null
      201230-82-2
    • In-stock
      2-Amino-2-methyl-1-propanol|CS-W013743
      124-68-5
    • ~92%
    • In-stock
      4,4-Dimethyloxazolidin-2-one|CS-W011238
      26654-39-7

    References

    • Li, Peng; Yuan, Xiaohua; Wang, Shudong; Lu, Shiwei Tetrahedron, 2007 , vol. 63, # 50 p. 12419 - 12423
  • Route3
    • In-stock
      2-Amino-2-methyl-1-propanol|CS-W013743
      124-68-5
    • null|null
      105-58-8
    • ~10%
    • In-stock
      4,4-Dimethyloxazolidin-2-one|CS-W011238
      26654-39-7

    References

    • Ito; Sasaki; Tamoto; Sunagawa; Terashima Tetrahedron, 1991 , vol. 47, # 16-17 p. 2801 - 2820

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   38.33
  • LogP   0.5048
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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