Description

(S)-4-fluoromethyl-dihydro-furan-2-one (CAS No. 916069-80-2) is a high-purity chiral lactone derivative with the molecular formula C₅H₇FO₂. This compound, also known by its IUPAC name (4S)-4-(fluoromethyl)oxolan-2-one, is a valuable fluorinated building block for pharmaceutical and agrochemical research. The (S)-enantiomer exhibits distinct stereochemical properties critical for asymmetric synthesis. Supplied as a clear to pale-yellow liquid (or low-melting solid depending on storage conditions), it is characterized by its lactone ring and reactive fluoromethyl group. Typical purity levels exceed 97% by GC analysis, with chiral purity >99% ee. This air-sensitive compound should be stored under inert atmosphere at 2-8°C. Offered in research quantities from 100mg to 10g with Certificate of Analysis, it’s particularly useful for developing fluorinated analogs of bioactive molecules.

Properties

• CAS Number: 916069-80-2
• Complexity: 103
• IUPAC Name: (4S)-4-(fluoromethyl)tetrahydrofuran-2-one
• InChI: InChI=1S/C5H7FO2/c6-2-4-1-5(7)8-3-4/h4H,1-3H2/t4-/m1/s1
• InChI Key: SNOBQHSFTVYKRO-SCSAIBSYSA-N
• Exact Mass: 118.04300762
• Molecular Formula: C5H7FO2
• Molecular Weight: 118.11
• SMILES: C1[C@@H](COC1=O)CF
• Topological: 26.3
• Monoisotopic Mass: 118.04300762
• Synonyms: (S)-4-fluoromethyl-dihydro-furan-2-one, DTXSID20475337, 813452-00-5, DTXCID20426147, (S)-4-(Fluoromethyl)dihydrofuran-2(3H)-one, 916069-80-2, 2(3H)-Furanone, 4-(fluoromethyl)dihydro-, (4S)-, SCHEMBL421883, SNOBQHSFTVYKRO-SCSAIBSYSA-N, AKOS015904516, (s)-3-fluoromethyl-gamma-butyrolactone, AC-30716, DB-328111

Application

This chiral fluorinated lactone serves as a key intermediate in the synthesis of biologically active compounds, particularly in CNS drug development. The fluoromethyl group enhances metabolic stability and membrane permeability in candidate molecules. Researchers utilize it for constructing fluorinated analogs of GABAergic compounds and other heterocyclic pharmacophores. Its stereospecificity makes it valuable for studying structure-activity relationships in medicinal chemistry programs.

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