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CS-W001157 4
Total: USD 88.00

(2S,6S)-2,6-Dimethylmorpholine

  • CAS No. 276252-73-4

  • Cat. No. CS-0102294
  • Molecule weight115.17
  • Purity≥97%
  • MDL No.MFCD18250271

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

(2S,6S)-2,6-Dimethylmorpholine|CS-0102294

Structure of 276252-73-4

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General Information

  • CAS No. 276252-73-4
  • Cat. No. CS-0102294
  • Purity ≥97%
  • MDL No. MFCD18250271
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₁₃NO
  • Molecular Weight 115.17
  • Synonym(s) (2S,6S)-2,6-Dimethyl-morpholine
  • SMILES C[C@@H]1O[C@@H](C)CNC1

Description

(2S,6S)-2,6-Dimethylmorpholine is a chiral, bench-stable heterocycle featuring two methyl groups at the 2- and 6-positions of the morpholine ring. This stereochemistry imparts distinct conformational rigidity and enhanced solubility in polar organic solvents. The molecule serves as a valuable scaffold in asymmetric synthesis, where its defined stereocenters enable predictable stereochemical outcomes in catalytic transformations.

Application

(2S,6S)-2,6-Dimethylmorpholine serves as a chiral, conformationally restricted heterocyclic scaffold widely employed in medicinal chemistry. Its stable, sterically defined structure facilitates predictable stereochemical control in synthetic transformations and functions as a versatile building block for bioactive molecule construction. The compound exhibits excellent bench stability, tolerates diverse functional groups, and enables efficient incorporation into complex molecular architectures through standard amine- and alcohol-directed reactions.

Synthesis

  • Route1
    • (2S,6S)-2,6-dimethylmorpholine (R)-2-hydroxy-2-phenylacetate|CS-0183876
      943344-44-3
    • ~88%
    • (R)-2-Hydroxy-2-phenylacetic acid  Pregabalin Impurity|CS-0167074
      611-71-2
    • In-stock
      (2S,6S)-2,6-Dimethylmorpholine|CS-0102294
      276252-73-4

    References

    • BASF SE Patent: US2009/12289 A1, 2009 ; Location in patent: Page/Page column 2 ;
  • Route2
    • (2s,6s)-4-Benzyl-2,6-dimethylmorpholine|CS-0661593
      276252-72-3
    • ~%
    • In-stock
      (2S,6S)-2,6-Dimethylmorpholine|CS-0102294
      276252-73-4

    References

    • Licandro, Emanuela; Maiorana, Stefano; Baldoli, Clara; Capella, Laura; Perdicchia, Dario Tetrahedron Asymmetry, 2000 , vol. 11, # 4 p. 975 - 980
  • Route3
    • null|null
      125948-52-9
    • ~%
    • In-stock
      (2S,6S)-2,6-Dimethylmorpholine|CS-0102294
      276252-73-4

    References

    • Licandro, Emanuela; Maiorana, Stefano; Baldoli, Clara; Capella, Laura; Perdicchia, Dario Tetrahedron Asymmetry, 2000 , vol. 11, # 4 p. 975 - 980

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   21.26
  • LogP   0.3832
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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