Cas no 133665-55-1 (sodium (2R)-2-fluoropropanoate)

Sodium (2R)-2-fluoropropanoate is a chiral fluorinated carboxylate salt with applications in pharmaceutical synthesis and organic chemistry. Its key advantages include its role as a versatile building block for introducing fluorine into target molecules, enhancing metabolic stability and bioavailability in drug development. The (2R)-stereochemistry provides selectivity in asymmetric synthesis, making it valuable for producing enantiomerically pure compounds. The sodium salt form ensures improved solubility in aqueous and polar solvents, facilitating handling and reactivity in various reaction conditions. Its stability under standard storage conditions and compatibility with common synthetic methodologies further contribute to its utility in research and industrial processes.
sodium (2R)-2-fluoropropanoate structure
133665-55-1 structure
Product Name:sodium (2R)-2-fluoropropanoate
CAS No:133665-55-1
MF:C3H4FNaO2
MW:114.050835609436
CID:6323106
PubChem ID:23681804
Update Time:2025-10-18

sodium (2R)-2-fluoropropanoate Chemical and Physical Properties

Names and Identifiers

    • 133665-55-1
    • sodium (2R)-2-fluoropropanoate
    • EN300-39852067
    • sodium;(2R)-2-fluoropropanoate
    • Inchi: 1S/C3H5FO2.Na/c1-2(4)3(5)6;/h2H,1H3,(H,5,6);/q;+1/p-1/t2-;/m1./s1
    • InChI Key: WDYHENABJMJFTR-HSHFZTNMSA-M
    • SMILES: [Na+].F[C@@H](C(=O)[O-])C

Computed Properties

  • Exact Mass: 114.00930181g/mol
  • Monoisotopic Mass: 114.00930181g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 7
  • Rotatable Bond Count: 1
  • Complexity: 66
  • Covalently-Bonded Unit Count: 2
  • Defined Atom Stereocenter Count: 1
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 40.1?2

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Additional information on sodium (2R)-2-fluoropropanoate

Recent Advances in the Application of Sodium (2R)-2-fluoropropanoate (CAS: 133665-55-1) in Chemical Biology and Pharmaceutical Research

Sodium (2R)-2-fluoropropanoate (CAS: 133665-55-1) has emerged as a compound of significant interest in the field of chemical biology and pharmaceutical research. This fluorinated derivative of propanoic acid is increasingly being utilized in the synthesis of novel bioactive molecules, particularly in the development of enzyme inhibitors and prodrugs. Recent studies have highlighted its potential as a key building block in medicinal chemistry due to its unique physicochemical properties and metabolic stability.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated the effectiveness of sodium (2R)-2-fluoropropanoate as a precursor in the synthesis of fluorinated analogs of clinically relevant drugs. The research team successfully incorporated this compound into the structure of several kinase inhibitors, resulting in improved target selectivity and reduced off-target effects. The fluorination at the 2-position was found to significantly enhance the metabolic stability of the resulting compounds while maintaining their biological activity.

In the area of positron emission tomography (PET) tracer development, sodium (2R)-2-fluoropropanoate has shown promise as a labeling precursor. A recent Nature Communications article (2024) described its use in the synthesis of fluorine-18 labeled tracers for imaging studies. The compound's stereochemical purity (R-configuration) was crucial for achieving high target specificity in these imaging agents, particularly for neurological targets where chirality plays a critical role in receptor binding.

Metabolic studies have revealed interesting aspects of sodium (2R)-2-fluoropropanoate's behavior in biological systems. Research published in Drug Metabolism and Disposition (2023) demonstrated that the compound undergoes selective metabolism, with the fluorine atom significantly altering its metabolic pathways compared to the non-fluorinated counterpart. This property is being exploited in the design of prodrugs that require controlled activation in specific tissues or cellular compartments.

The pharmaceutical industry has taken notice of sodium (2R)-2-fluoropropanoate's potential, with several companies including it in their synthetic routes for investigational new drugs. Patent filings from 2023-2024 show its application in antiviral compounds, particularly in the development of nucleotide analogs targeting RNA viruses. The fluorine substitution has been shown to improve membrane permeability and intracellular retention of these therapeutic candidates.

Ongoing research is exploring the use of sodium (2R)-2-fluoropropanoate in targeted protein degradation strategies. Preliminary results presented at the 2024 American Chemical Society meeting suggest that fluorinated compounds derived from this building block can enhance the formation and stability of ternary complexes in PROTAC (Proteolysis Targeting Chimera) systems, potentially opening new avenues for drug discovery in challenging target classes.

As the field of fluorinated pharmaceuticals continues to expand, sodium (2R)-2-fluoropropanoate (CAS: 133665-55-1) is positioned to play an increasingly important role. Its combination of synthetic accessibility, stereochemical purity, and favorable biological properties make it a versatile tool for medicinal chemists working across multiple therapeutic areas. Future research directions likely include further optimization of synthetic methodologies and expanded applications in biologics conjugation and radiopharmaceutical development.

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