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CS-W001157 4
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(R)-Methyl 2-hydroxy-3-phenylpropanoate

  • CAS No. 27000-00-6

  • Cat. No. CS-W019028
  • Purity≥98%
  • MDL No.None

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

(R)-Methyl 2-hydroxy-3-phenylpropanoate|CS-W019028

Structure of 27000-00-6

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General Information

  • CAS No. 27000-00-6
  • Cat. No. CS-W019028
  • Purity ≥98%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₁₂O₃
  • Molecular Weight 180.20
  • Synonym(s) Methyl (R)-2-Hydroxy-3-phenylpropionate
  • SMILES O=C(OC)[C@H](O)CC1=CC=CC=C1

Description

(R)-Methyl 2-hydroxy-3-phenylpropanoate is a chiral ester featuring a stereogenic center at the 2-position, bearing a hydroxyl group and a phenyl-substituted propionate backbone. This configuration imparts distinct stereochemical control in asymmetric synthesis, enabling selective transformations in pharmaceutical intermediates and natural product derivatization. The molecule exhibits enhanced stability under standard bench conditions, facilitating reliable handling in synthetic workflows.

Application

(R)-Methyl 2-hydroxy-3-phenylpropanoate serves as a versatile chiral building block for the synthesis of β-hydroxy esters and related pharmaceutical intermediates. Its well-defined stereochemistry enables reliable asymmetric transformations, while the pendant hydroxyl and phenyl groups offer orthogonal handles for further functionalization. The compound exhibits excellent bench stability and is readily purified by standard chromatographic methods, making it ideal for iterative synthesis workflows in medicinal chemistry and process development.

Synthesis

  • Route1
    • null|null
      100-39-0
    • ~%
    • In-stock
      (R)-Methyl 2-hydroxy-3-phenylpropanoate|CS-W019028
      27000-00-6

    References

    • Ley, Steven V.; Diez, Elena; Dixon, Darren J.; Guy, Richard T.; Michel, Patrick; Nattrass, Gillian L.; Sheppard, Tom D. Organic and Biomolecular Chemistry, 2004 , vol. 2, # 24 p. 3608 - 3617
  • Route2

    References

    • Storz, Thomas; Dittmar, Peter; Fauquex, Pierre Francois; Marschal, Philippe; Lottenbach, Willy Urs; Steiner, Heinz Organic Process Research and Development, 2003 , vol. 7, # 4 p. 559 - 570
  • Route3
    • In-stock
      DL-3-Phenyllactic acid|CS-W017878
      828-01-3
    • null|null
      74-88-4
    • ~%
    • In-stock
      (R)-Methyl 2-hydroxy-3-phenylpropanoate|CS-W019028
      27000-00-6

    References

    • Hoffman, Robert V.; Tao, Junhua Journal of Organic Chemistry, 1997 , vol. 62, # 7 p. 2292 - 2297

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   46.53
  • LogP   0.763
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   3

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