Ethyl 2-fluoro-3-hydroxybutanoate - ≥95% , CAS No.37032-41-0

CAS: 37032-41-0 Cat. No.: E973290 Fórmula: C₆H₁₁FO₃ Peso molecular: 150.150 Número EC: 863-592-7

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Especificaciones y pureza

≥95%

Condiciones de almacenamiento de almacenamiento

Room temperature

Pureza

≥95%

Nombres e identificadores

• Sonrisas canónicas: CCOC(=O)C(C(C)O)F
• IUPAC Name: ethyl 2-fluoro-3-hydroxybutanoate
• InChIKey: GQURZXWOXDVWTD-UHFFFAOYSA-N
• INCHI: 1S/C6H11FO3/c1-3-10-6(9)5(7)4(2)8/h4-5,8H,3H2,1-2H3
• Peso molecular: 150.150

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Clase Hydroxy acids and derivatives
      • Subclass Beta hydroxy acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Clase: Hydroxy acids and derivatives
• Subclass: Beta hydroxy acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Beta hydroxy acids and derivatives
• Alternative Parents: Fatty acid esters Alpha-halocarboxylic acid derivatives Secondary alcohols Fluorohydrins Carboxylic acid esters Monocarboxylic acids and derivatives Organofluorides Organic oxides Hydrocarbon derivatives Carbonyl compounds Alkyl fluorides
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Beta-hydroxy acid - Fatty acid ester - Fatty acyl - Alpha-halocarboxylic acid derivative - Alpha-halocarboxylic acid or derivatives - Carboxylic acid ester - Secondary alcohol - Fluorohydrin - Halohydrin - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Alkyl halide - Alkyl fluoride - Alcohol - Carbonyl group - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Organohalogen compound - Organofluoride - Organooxygen compound - Aliphatic acyclic compound
• Descripción: This compound belongs to the class of organic compounds known as beta hydroxy acids and derivatives. These are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Propiedades químicas y físicas

• Peso molecular: 150.150 g/mol
• XLogP3: 0.600
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 150.069 Da
• Monoisotopic Mass: 150.069 Da
• Topological Polar Surface Area: 46.500 Ų
• Heavy Atom Count: 10
• Formal Charge: 0
• Complexity: 116.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 2
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Application Protocols

Not applicable. No biological assay protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule reagent. For synthetic usage, see Reaction Conditions and Application notes in other sections.

Biological Roles

This compound is a synthetic, small organofluorine β-hydroxy ester and does not have an established role in natural biochemistry.

• General context (literature):
  • Organofluorine motifs are rare in nature; introduction of fluorine adjacent to carbonyls modulates acidity, conformation, and metabolic stability when embedded in larger molecules.
  • β-Hydroxy esters can participate in enzyme-catalyzed acylations/oxidations in model systems, but Ethyl 2-fluoro-3-hydroxybutanoate itself is not a known metabolite or cofactor.
• Utility in chemical biology (research-only):
  • Serves as a building block to prepare probe molecules where α-F substitution tunes binding or reactivity, facilitating SAR investigations.

No biological activity or clinical claims are made. For research use only.

Buffer Applications

Not typically applicable. Ethyl 2-fluoro-3-hydroxybutanoate is not a buffering agent and lacks a conjugate acid–base pair with a useful aqueous pKa in the physiological range. For aqueous manipulations, select an external buffer system (e.g., phosphate, HEPES) compatible with esters, and see Reaction & Applications/Solvent Selection for guidance on handling and extraction.

Green Alternatives

Greener choices can be implemented primarily in solvent selection and oxidation/protection strategies rather than in the substrate itself.

• Solvent alternatives:
  • Replace dichloromethane with ethyl acetate or 2-MeTHF where feasible (workups, extractions, and some oxidations/protections).
  • Use ethanol or isopropanol as reaction media for transesterification/hydrolysis when compatible, minimizing VOC impact.
• Oxidation choices:
  • Favor catalytic TEMPO/NaOCl in aqueous biphasic systems or Oxone®-mediated protocols over chromium(VI) reagents for β-OH to keto conversions.
• Protection strategies:
  • Prefer carbonate protections (e.g., vinyl/allyl carbonates removable under Pd catalysis) over persistent silyl groups when lifecycle impact matters.

Comparison (general):

• DCM vs EtOAc
  • Environmental: DCM (halogenated, higher EHS concerns) vs EtOAc (biobased potential, readily biodegradable).
  • Performance: Both dissolve this ester well; EtOAc may be less optimal for strong Lewis-acidic conditions but often adequate.
• THF vs 2-MeTHF
  • Environmental: 2-MeTHF is biorenewable, higher boiling, reduced peroxide issues; THF forms peroxides and is fossil-derived.
  • Performance: 2-MeTHF offers similar solvation; water content and phase behavior can aid extractions.

Trade-offs: Greener alternatives may alter rates/selectivities (e.g., in Mitsunobu or Swern-type oxidations). Validate on small scale before scale-up.

Pharmaceutical Uses

• Formulation/excipient role: None specified. This compound is not a standard excipient.
• Research/manufacturing context (literature):
  • Employed as a synthetic intermediate for medicinal chemistry programs seeking α-fluorinated carbonyl motifs to modulate physicochemical properties (pKa, lipophilicity, conformation) of candidate molecules.
  • The β-hydroxy handle enables rapid access to analog series via oxidation, substitution, or protection–deprotection sequences under GMP-like development workflows.
• Regulatory status: Not a pharmacopeial article to our knowledge; no compendial monograph indicated in the Product Data.

Note: No therapeutic or clinical claims are implied. For research and process development use only.

Physical Properties

Item-specific values are not provided in the Product Data; consult the CoA/SDS for specifications.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Density, refractive index, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
• Melting/boiling point: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility profile (general guidance, literature):
  • Expected to be miscible or highly soluble in common organic solvents such as dichloromethane, ethyl acetate, THF, acetone, acetonitrile, and lower alcohols (MeOH, EtOH), owing to the ester and hydroxyl functionalities.
  • Limited solubility anticipated in nonpolar alkanes; moderate in toluene/Et2O.
  • Very low solubility in water, though the free OH may permit slight partitioning to aqueous phases at higher pH due to hydrogen bonding.
• Acid–base properties (literature expectations): secondary alcohol pKa typically ~16–18 in DMSO; ester is not basic; overall neutral at ambient pH.
• Partitioning (literature expectations): logP likely in the low-to-moderate range for small oxygenated esters with one F; exact value not specified.

Practical note: The β-hydroxy ester motif can form intra-/intermolecular hydrogen bonds; viscosity and polarity are higher than for the corresponding deoxy analog. Handle as a typical low-molecular-weight oxygenated liquid/low-melting solid unless otherwise specified on the CoA.

Quality and Grades

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

Interpretation and implications:

• In the absence of a declared grade (e.g., Analytical Reagent, Synthesis, HPLC, or GMP-related grades), this item should be treated as a research-grade reagent for laboratory use only (per Research Use Note).
• Purity reporting: The CoA will typically include assay purity (e.g., GC/HPLC area %), and may include residual solvent levels and water (Karl Fischer). When these are critical to your application (e.g., enantioselective catalysis or polymerizations), request the current CoA/Spec Sheet.
• Stabilizers/inhibitors: None are specified. If your transformation is sensitive to acids/bases, you may wish to pre-wash, distill (if feasible), or pass through basic alumina to remove trace acidic impurities; verify compatibility to avoid promoting ester hydrolysis or β-hydroxy dehydration.
• Optical purity: Stereochemistry is not specified. If enantio- or diastereopurity is important, confirm by chiral HPLC/GC or NMR with chiral shift reagents.
• Batch-to-batch consistency: For building-block applications, track impurity profiles (e.g., dehydrated α,β-unsaturated ester or oxidized β-keto ester byproducts) as part of your quality acceptance criteria.

Reaction and Applications

Ethyl 2-fluoro-3-hydroxybutanoate is a versatile α-fluoro-β-hydroxy ester that serves as a handle for constructing fluorinated motifs with control over oxidation state and stereochemistry.

• Transformations centered on the β-hydroxy group:
  • Oxidation to the β-keto ester (ethyl 2-fluoro-3-oxobutanoate) using DMP, PCC, or Swern (0–25 °C), enabling further enolate chemistry and cross-couplings via enol derivatives.
  • Activation/inversion: Convert OH to mesylate/tosylate or use Mitsunobu conditions to access inverted ethers, azides, or other C–O/N–C substitution products.
  • Protection strategies: Silyl ethers (TBS/TBDPS) or acylation (Ac2O) to mask the OH during base- or acid-sensitive steps.
• Chemistry at the α-fluoro center:
  • The α-F inductively activates the carbonyl, influencing enolate geometry and acidity; consider this in aldol/alkylation planning. Direct displacement of F is generally unfavorable; instead, leverage enolate or elimination pathways.
  • Dehydration of the β-hydroxy ester affords an α,β-unsaturated α-fluoro enoate, useful in conjugate additions and as a handle for further elaboration.
• Ester modifications:
  • Saponification to the corresponding acid, followed by coupling (amide formation/ester exchange).
  • Reduction (LiAlH4, DIBAL-H conditions tuned) to furnish diols or lactol-like intermediates; control chemoselectivity to preserve the C–F bond.
• Stereochemical considerations:
  • The β-OH center is settable/enantioconvertible via Mitsunobu; kinetic resolution and enzymatic acylations are also viable.

Applications include medicinal chemistry lead modification (introducing α-F effects on pKa, lipophilicity), synthesis of fluorinated building blocks, and study of neighboring group participation in fluorinated carbonyl systems. Always verify compatibility of reagents with ester functionality to avoid undesired hydrolysis.

Reaction Conditions

General literature guidance for common manipulations of α-fluoro-β-hydroxy esters. Optimize for your substrate and scale.

• Oxidation (β-OH → β-keto ester):
  • Dess–Martin periodinane (1.2–1.5 equiv) in DCM, 0–25 °C, 0.5–2 h; quench with Na2S2O3/NaHCO3. Typical good to excellent yields for secondary alcohol oxidations.
  • TEMPO (2–5 mol%), NaOCl (1.5–2.0 equiv active chlorine), KBr (catalytic), pH 8–9, biphasic EtOAc/H2O, 0–5 °C to room temp.
• Dehydration (to α,β-unsaturated α-fluoro enoate):
  • MsCl (1.2–1.5 equiv), Et3N (2–3 equiv) in DCM, 0 °C → rt, followed by base-promoted E2; or POCl3/pyridine (Vilsmeier-type) at 0–25 °C.
• Mitsunobu substitution at C3:
  • Alcohol (1.0 equiv), nucleophile (1.2–2.0 equiv), PPh3 (1.2 equiv), DEAD/DIAD (1.2 equiv) in THF or toluene, 0 °C → rt. Strictly anhydrous.
• Protection (TBS ether):
  • TBS-Cl (1.2–1.5 equiv), imidazole (2.0 equiv) in DMF or DCM, rt, 2–4 h. Acidic or fluoride workups remove the silyl group.
• Saponification/transesterification:
  • NaOH or K2CO3 in MeOH/H2O (1–2 M), 0–25 °C, 0.5–4 h to acid (then acidify). Acidic methanol (cat. H2SO4) for Fischer transesterification.
• Reductions (exercise caution to avoid overreduction):
  • DIBAL-H (1.0–1.5 equiv) in toluene at −78 to −40 °C toward aldehyde equivalents; quench carefully.

Notes:

• Maintain neutral-to-mildly basic conditions to avoid undesired ester cleavage when not intended.
• The α-F group can influence rates/selectivities; monitor by TLC/GC/LC–MS and adjust equivalents/temperature accordingly.
• All conditions above are general literature guidance for this functional class; verify on small scale.

Safety and Handling

• GHS classification, signal word, pictograms, and H-statements: Not specified for this item; refer to the SDS for authoritative hazard information.
• General hazards (literature-based for small β-hydroxy esters): May cause skin/eye irritation and respiratory tract irritation. Avoid inhalation of vapors/mists and avoid contact with skin and eyes.
• Personal protective equipment (PPE):
  • Wear lab coat, safety glasses or face shield, and appropriate chemical-resistant gloves (e.g., nitrile). Use in a fume hood to minimize inhalation exposure.
• Handling guidance:
  • Keep containers tightly closed. Minimize exposure to moisture and strong acids/bases which can promote ester hydrolysis and/or dehydration of the β-hydroxy group.
  • Avoid strong oxidizers and strong reducing agents. Secondary alcohol may be oxidized by strong oxidants; ester can be saponified under basic conditions.
• Storage conditions: Room temperature (per Product Data). Store in a cool, dry, well-ventilated area away from incompatible reagents. For long-term integrity, consider storing under inert gas to limit moisture uptake.
• First-aid overview (general):
  • Skin/eye contact: Rinse with plenty of water for at least 15 minutes; remove contaminated clothing; seek medical attention if irritation persists.
  • Inhalation: Move to fresh air; provide oxygen if needed; seek medical attention if symptoms occur.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.

Always consult the product-specific SDS for definitive safety, environmental, and regulatory guidance. Research use only.

Solvent Selection

This product is typically used as a substrate or intermediate rather than as a solvent. Choose solvents that solubilize both the ester and the reagents while preserving the β-hydroxy functionality.

• Polarity and miscibility (general expectations):
  • High solubility in polar aprotic media (DCM, THF, EtOAc, MeCN, acetone) and lower alcohols (MeOH, EtOH).
  • Moderate solubility in aromatic/aprotic media (toluene, diethyl ether). Limited in alkanes (hexanes/heptane).
• Selection guidance by operation:
  • Oxidations of the secondary alcohol: DCM or EtOAc are common for DMP/PCC; MeCN for TEMPO/BAIB; avoid aqueous base during oxidation to prevent saponification.
  • Protection as silyl ether: DMF or DCM with imidazole or pyridine base; THF with TBDMS-Cl/Et3N.
  • Mitsunobu or substitution chemistry at C3–OH: THF, toluene, or DCM; strictly anhydrous conditions.
  • Hydrolysis/transesterification: MeOH/EtOH with catalytic acid/base; aqueous MeOH for saponification.
  • Dehydration to α,β-unsaturated fluoroester: Pyridine or toluene with reagents such as POCl3 or MsCl/Et3N.
• Comparison notes:
  • THF vs DCM: THF offers better solubility for bases/nucleophiles, but can participate in side reactions under strong Lewis acidity; DCM often cleaner for electrophilic oxidations.
  • EtOAc is a greener alternative to DCM for many operations with comparable solubility for this substrate.

Storage and Reconstitution

• Storage conditions (per Product Data): Room temperature.
• Container and atmosphere: Store tightly closed in glass with PTFE-lined cap. For extended storage, consider an inert atmosphere (N2/Ar) and desiccation to limit moisture-driven hydrolysis or β-hydroxy dehydration.
• Light sensitivity: Not specifically indicated; as good practice for organofluorine esters, protect from prolonged light exposure.
• Reconstitution: Supplied neat; no reconstitution required. To prepare solutions, use dry, oxygen-free solvents when moisture-sensitive transformations are planned.
• Stability considerations (general):
  • Avoid strong acids/bases that promote ester hydrolysis or dehydration of the β-hydroxy group.
  • Avoid strong oxidants/reductants unless those transformations are intended.
• Shipping: Not specified for this item; refer to CoA/Spec Sheet.
• Usage note: For research use only (as stated in Product Data).

Structure and Identity

Ethyl 2-fluoro-3-hydroxybutanoate is an organofluorine β-hydroxy ester useful as a chiral or racemic building block in synthesis.

• Item-specific identifiers (from Product Data):
  • CAS: 37032-41-0
  • CID: 71360732
  • InChIKey: 109136 (as provided)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Computed/literature structural data (for reference; not item-specific specifications):
  • Molecular formula (derived from name): C6H11FO3 (literature/computed)
  • Molecular weight: ~150.15 g/mol (literature/computed)
  • Core functional groups: ethyl ester (–C(=O)OEt), secondary alcohol (–CHOH–), and an α-fluoro substituent adjacent to the carbonyl.
  • Stereochemistry: The 3-hydroxy center is stereogenic; product may be racemic unless specified. The α-carbon (C-2) bearing F is also stereogenic if fully substituted; the common naming here implies 2-substitution on the butanoate chain with F and 3-substitution with OH.
• 2D structure (verbal description): An ethyl ester of a substituted butanoate in which the carbonyl carbon (C1) is bound to an α-carbon (C2) carrying fluorine, the β-carbon (C3) carries a hydroxyl group, and the terminal (C4) is a methyl; the ester oxygen bears an ethyl group.
• Structural class and features: small, polar, H-bond donor/acceptor; α-fluoro-β-hydroxy ester motif often used in stereocontrolled elaborations.

Note: Exact line notations (SMILES/InChI) and definitive stereochemistry are not specified for this item; refer to CoA/Spec Sheet for authoritative identifiers.

Synthetic Utility

Key functional handles and their exploitation:

• β-Hydroxy (secondary alcohol):
  • Oxidation to β-keto ester unlocks enolate chemistry (Claisen-type condensations, Michael additions via enolates or silyl enol ethers).
  • Activation (MsCl/TsCl) enables SN2 substitutions (inversion) with O-, N-, S-nucleophiles; Mitsunobu provides a complementary route with inversion.
  • Protection as TBS/TBDPS ethers preserves the α-F stereocenter during basic steps.
• α-Fluoro center:
  • Strong −I effect stabilizes the conjugate base and biases enolate geometry; leverage for diastereoselective alkylations.
  • Dehydration of the β-hydroxy ester forms α-fluoro-enoates suitable for conjugate additions (e.g., cuprates, organozincs) or cycloadditions.
• Ester functionality:
  • Transesterification to tailor leaving groups; saponification → acid → amide couplings (EDC/HATU) to embed the motif in peptidomimetics.
  • Selective reductions (DIBAL-H to aldehyde equivalents at low temperature; LiAlH4 to diols) with attention to C–F retention.

Retrosynthetic value:

• Serves as a masked 1,3-difunctional synthon (C–OH/C=O), enabling convergent assembly of fluorinated polyketide fragments or as a platform for β-substituted α-fluoro acids/esters via substitution–elaboration at C3.

Target Specificity

Not applicable. This product is a small-molecule chemical building block and is not an affinity reagent, antibody, or biologic. No target, epitope, clone, or species reactivity applies.