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CS-W001157 4
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2-Cyclohexyl-2-hydroxyacetic acid

  • CAS No. 4442-94-8

  • Cat. No. CS-0465551
  • Purity≥95%
  • MDL No.MFCD00068380

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

2-Cyclohexyl-2-hydroxyacetic acid|CS-0465551

Structure of 4442-94-8

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General Information

  • CAS No. 4442-94-8
  • Cat. No. CS-0465551
  • Purity ≥95%
  • MDL No. MFCD00068380
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₁₄O₃
  • Molecular Weight None
  • Synonym(s) Cyclohexyl(hydroxy)acetic acid
  • SMILES C1CCC(CC1)C(C(=O)O)O

Description

2-Cyclohexyl-2-hydroxyacetic acid features a cyclohexyl group flanking a hydroxylated acetic acid core, delivering enhanced lipophilicity and metabolic stability. This structural motif enables direct integration into bioactive scaffolds, serving as a robust building block for pharmaceutical intermediates and functionalized polymers under standard conditions.

Application

2-Cyclohexyl-2-hydroxyacetic acid serves as a versatile chiral building block in synthetic organic chemistry, enabling the construction of biologically relevant heterocyclic scaffolds and functionalized alcohols. Its α-hydroxy acid functionality facilitates stereoselective transformations, including esterification, amidation, and cyclization reactions. The cyclohexyl group provides enhanced lipophilicity and conformational rigidity, improving metabolic stability in downstream applications. Bench-stable and readily purified by recrystallization, it functions effectively in both laboratory-scale synthesis and process development workflows.

Synthesis

  • Route1
    • (R)-2-Hydroxy-2-phenylacetic acid  Pregabalin Impurity|CS-0167074
      611-71-2
    • ~82%
    • In-stock
      2-Cyclohexyl-2-hydroxyacetic acid|CS-0465551
      4442-94-8

    References

    • Board of Trustees of Michigan State University Patent: US2007/142461 A1, 2007 ; Location in patent: Page/Page column 6 ;
  • Route2
    • Methyl 2-cyclohexyl-2-hydroxyacetate|CS-0587127
      99183-16-1
    • ~75%
    • In-stock
      2-Cyclohexyl-2-hydroxyacetic acid|CS-0465551
      4442-94-8

    References

    • ARETE THERAPEUTICS, INC. Patent: WO2008/73623 A2, 2008 ; Location in patent: Page/Page column 114; 115 ;
  • Route3
    • (R)-2-Cyclohexyl-2-hydroxyacetonitrile|CS-0617518
      100007-62-3
    • ~81%
    • In-stock
      2-Cyclohexyl-2-hydroxyacetic acid|CS-0465551
      4442-94-8

    References

    • Roxburgh, Craig J.; Ganellin, C. Robin; Thorpe, Andrew J. Synlett, 2007 , # 8 p. 1211 - 1214

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 : P260-P264-P270-P271-P280-P301+P310-P302+P352-P304+P340-P305+P351+P338-P312-P330-P332+P313-P337+P313-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   57.53
  • LogP   1.0122
  • H_Acceptors   2
  • H_Donors   2
  • Rotatable_Bonds   2

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