Ethyl 2-hydroxy-2-(oxolan-3-yl)acetate - ≥95% , CAS No.221546-88-9

CAS: 221546-88-9 Cat. No.: E946604 Summenformel: C₈H₁₄O₄ Molekulargewicht: 174.190 EG-Nummer: 829-727-9

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Spezifikationen & Reinheit

≥95%

Storage

Room temperature

Reinheit

≥95%

Namen und Kennungen

• Kanonisches Lächeln: CCOC(=O)C(C1CCOC1)O
• IUPAC Name: ethyl 2-hydroxy-2-(oxolan-3-yl)acetate
• InChIKey: ZLHNHDYYRVHBSP-UHFFFAOYSA-N
• INCHI: 1S/C8H14O4/c1-2-12-8(10)7(9)6-3-4-11-5-6/h6-7,9H,2-5H2,1H3
• Molekulargewicht: 174.190

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Klasse Oxolanes

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Klasse: Oxolanes
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Oxolanes
• Alternative Parents: Secondary alcohols Carboxylic acid esters Oxacyclic compounds Monocarboxylic acids and derivatives Dialkyl ethers Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Oxolane - Secondary alcohol - Carboxylic acid ester - Oxacycle - Monocarboxylic acid or derivatives - Ether - Dialkyl ether - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Alcohol - Aliphatic heteromonocyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as oxolanes. These are organic compounds containing an oxolane (tetrahydrofuran) ring, which is a saturated aliphatic five-member ring containing one oxygen and five carbon atoms.
• 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

Chemische und physikalische Eigenschaften

• Molekulargewicht: 174.190 g/mol
• XLogP3: 0.100
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 174.089 Da
• Monoisotopic Mass: 174.089 Da
• Topological Polar Surface Area: 55.800 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 157.000
• 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 immunoassay or bioanalytical application protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule reagent. Users should develop synthetic or analytical procedures appropriate to their research goals.

Biological Roles

This product is a small-molecule synthetic building block and is not intended for biological function studies as supplied.

General context (literature, not product-specific):

• α‑Hydroxy esters occur widely in metabolism (e.g., glycolate derivatives), but the presence of a tetrahydrofuran ring here makes this compound non-natural.
• Such motifs can be used to construct oxygen-rich frameworks found in natural products for SAR or probe development in research settings.

No biological activity, targets, or pathways are specified for this item. Any use in biochemical assays should be validated by the end user. For research use only (per Product Data).

Buffer Applications

Not typically applicable. Ethyl 2-hydroxy-2-(oxolan-3-yl)acetate is not a buffering agent and lacks a suitable conjugate acid/base pair in the physiological pH range. For aqueous work, focus on its solubility and stability in the chosen buffer rather than using it to prepare a buffer system.

Green Alternatives

While Ethyl 2-hydroxy-2-(oxolan-3-yl)acetate is itself a building block rather than a process solvent, greener choices can be made in its use and transformations.

Greener solvent choices for typical operations (literature/guidance):

• Replace DCM/CHCl3 with ethyl acetate, 2‑MeTHF, or CPME for extractions and reactions when compatible with the chemistry.
• Use MeOH/EtOH or IPA in place of acetonitrile where solubility allows.
• Employ water-lean biphasic systems (EtOAc/water) for workups to reduce halogenated waste.

Comparison snapshot (informational):

• DCM vs EtOAc
  • Hazard: chlorinated solvent, higher toxicity vs low-toxicity bio-based option.
  • Performance: DCM offers higher density and volatility; EtOAc often adequate for acylations and chromatographic elution with minor adjustments.
• THF vs 2‑MeTHF/CPME
  • 2‑MeTHF and CPME exhibit improved peroxide stability profiles and better sustainability metrics; they can often substitute THF in protection, acylation, and coupling steps.

Operational suggestions:

• Opt for catalytic, atom-economical transformations (e.g., catalytic oxidations with O2 or H2O2 under appropriate conditions) when converting the α‑OH to carbonyl.
• Minimize protecting-group steps by leveraging chemoselective reagents; if protection is required, choose easily cleavable, low-toxicity silyl or carbonate groups.

Pharmaceutical Uses

No pharmacopeial grade or excipient role is specified for this item. This compound is offered for research use as a synthetic intermediate.

General context (not a claim for this item):

• α‑Hydroxy esters and THF-containing fragments are common motifs in medicinal chemistry libraries and may be incorporated during lead optimization.
• Any use in cGMP or clinical manufacturing would require appropriate qualification, impurity profiling, and change control—outside the scope of this research product.

Physical Properties

Item-specific specifications (BP/MP, density, UV cutoff, elemental limits) are not provided in the Product Data for SKU E946604. Consult the CoA/Spec Sheet for definitive values.

General/literature expectations for Ethyl 2-hydroxy-2-(oxolan-3-yl)acetate (informational, not item specifications):

• Molecular formula (computed from structure): ~C8H14O4
• Molecular weight: ~174.19 g/mol
• Phase/appearance: Not specified for this item; refer to CoA/Spec Sheet. α-Hydroxy ethyl esters of this size are often low-melting solids or colorless liquids (literature, varies by sample and enantiomeric composition).
• Solubility profile (literature/generic):
  • Miscible with many organic solvents of intermediate polarity (e.g., EtOAc, CH2Cl2, MeOH, THF).
  • Limited solubility expected in very nonpolar alkanes; slightly water-soluble due to the α-OH and ester groups.
• Hydrogen-bonding: donor (1× OH) and acceptor (ester carbonyl and THF oxygen), enabling strong intermolecular interactions and potential for chelation to metals in solution.
• pKa: α-hydroxyl pKa for related secondary alcohols typically ~15–17 in DMSO (literature); not typically titratable in water.
• LogP: α-hydroxy esters with a THF ring generally exhibit moderate polarity (estimated cLogP in the ~0.5–1.5 range; literature estimates vary). Not specified for this item.
• Refractive index, density, BP/MP: Not specified for this item; refer to CoA/Spec Sheet.

Quality and Grades

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

Guidance on grades (general information for chemists evaluating fit-for-use):

• Research/technical grade α-hydroxy esters are typically suitable for synthetic applications, asymmetric catalysis screening, and building-block use. If low UV background is needed (e.g., LC or photochemical studies), request HPLC/LCMS grade or a UV-profiled lot.
• Stabilizers: None are indicated in the Product Data. If a stabilizer is used in any lot, it will be declared on the CoA/Spec Sheet. α-Hydroxy esters are generally stable without inhibitors but can slowly undergo transesterification or hydrolysis if contaminated with strong acid/base or moisture under heat.
• Typical QC for this class (informational):
  • Identity by 1H/13C NMR and MS; purity by GC or HPLC; water by Karl Fischer when relevant to the application.
  • Chiral information (ee/er) only applies if an enantioenriched lot is offered; none is specified for this item.

Reaction and Applications

Ethyl 2-hydroxy-2-(oxolan-3-yl)acetate is a versatile α-hydroxy ester integrating a THF ring. It serves as a chiral pool precursor (when resolved) or as a racemic building block for constructing oxygen-rich scaffolds.

Representative application areas (literature/generic):

• Protection/derivatization of the α‑OH:
  • Formation of O-acyl, O‑silyl (TBS/TIPS/ TBDMS), or cyclic carbonate derivatives to modulate reactivity and control downstream chemoselectivity.
• α‑Functionalization strategies:
  • Mitsunobu inversion at the α‑carbon (via OH activation) to access the inverted ester or to form C–O/C–N bonds with nucleophiles.
  • Conversion to the α‑halo ester (e.g., via SOCl2/PPh3-CCl4 or Appel-type protocols) for subsequent SN1/SN2 substitutions or reductive couplings.
  • Oxidation of the secondary alcohol to the corresponding α‑keto ester (Dess–Martin, Swern) enabling enolate chemistry, aldol additions, and Strecker-type transformations.
• Carbon–carbon bond construction:
  • Reformatsky-type additions using the α‑halo derivative to add across carbonyls.
  • Decarboxylative couplings after hydrolysis to the acid and conversion to NHP or redox-active esters (Ni/photoredox, literature).
• THF ring as a masked 1,4-diol synthon:
  • Ring opening (acidic conditions or nucleophiles) to furnish ω‑hydroxy substituted chains; useful in polyol synthesis.
• Asymmetric synthesis context:
  • If enantioenriched, serves as a handle for stereocontrolled elaborations; neighboring-group participation from the α‑oxygen can direct outcomes in acylations or substitutions.

Practical tips:

• Maintain anhydrous conditions for base- or acid-sensitive steps (the α‑OH and ester are prone to transesterification/hydrolysis under harsh conditions).
• For selective O‑ vs C‑acylation, tune base (e.g., pyridine vs tertiary amines) and temperature; monitor closely by TLC/LCMS.

Reaction Conditions

General literature guidance for transformations of α-hydroxy ethyl esters (not item specifications):

• Protection of the α‑OH:
  • Silylation: TBSCl (1.2–1.5 equiv), imidazole or Et3N, DMF or DCM, 0–25 °C, 1–4 h. Typical isolated yields: 80–95% (literature for analogous substrates).
  • Acylation: Ac2O or benzoyl chloride (1.1–1.5 equiv), pyridine or DMAP catalysis, DCM, 0–25 °C.
• Oxidation to α‑keto ester:
  • Dess–Martin periodinane (1.3 equiv), DCM, 0–25 °C, 0.5–2 h; or Swern oxidation (DMSO, oxalyl chloride, −78 to 0 °C) followed by Et3N. Typical yields 70–90% on related substrates.
• Activation/substitution at α‑carbon:
  • Mitsunobu: DEAD/DIAD (1.2–1.5 equiv), PPh3 (1.2–1.5 equiv), nucleophile ROH/RNH2, THF or toluene, 0–25 °C; inversion at Cα expected.
  • Halogenation: SOCl2 or PPh3/CBr4 to form α‑halo esters under cold conditions; subsequent SN reactions in polar aprotic solvents (DMF, MeCN) with appropriate nucleophiles.
• Hydrolysis/transesterification:
  • Base-catalyzed saponification (NaOH/MeOH–H2O, 0–25 °C) to the acid; or acid-catalyzed exchange (ROH, catalytic TsOH), reflux.
• Ring opening of THF (when desired):
  • Strong Brønsted acids (e.g., H2SO4) or Lewis acids (BF3·Et2O) at 0–25 °C to promote regioselective opening, followed by trapping with nucleophiles.

Always adapt solvent and temperature to the specific substrate and scale; monitor by TLC/LCMS and quench cautiously to avoid ester hydrolysis.

Safety and Handling

Hazard classification details are not provided in the Product Data for this item. Always consult the product SDS for authoritative, up-to-date hazard, toxicological, and ecological information.

• GHS information (from Product Data):
  • Signal Word: Not specified for this item; refer to SDS.
  • H-Statements: Not specified for this item; refer to SDS.
  • GHS Classification/Pictograms: Not specified for this item; refer to SDS.
• Likely hazards (general guidance for α-hydroxy esters and cyclic ethers; not product-specific):
  • May cause skin/eye irritation and respiratory tract irritation upon exposure to vapors or aerosols.
  • Combustible organic; keep away from ignition sources.
• PPE and engineering controls:
  • Wear lab coat, safety glasses, and appropriate chemical-resistant gloves (e.g., nitrile). Work in a fume hood to control vapors and avoid inhalation of mists.
• Incompatibilities and reactivity (general):
  • Avoid strong oxidizers and strong bases (base-catalyzed transesterification/saponification possible).
  • Reactive with strong dehydrating agents/acyl activators (may form esters/ethers).
• First-aid overview (general):
  • Skin/eye contact: Rinse with water for ≥15 minutes; remove contaminated clothing; seek medical attention if irritation persists.
  • Inhalation: Move to fresh air; seek medical attention if symptoms occur.
  • Ingestion: Rinse mouth; do not induce vomiting; obtain medical attention.
• Additional notes:
  • Unlike acyclic dialkyl ethers, the tetrahydrofuran ring can form peroxides over time when present as a bulk solvent; however, in this compound it is a structural moiety, not a solvent. Peroxide testing is generally unnecessary for the neat reagent, but good storage practices still apply.

Solvent Selection

This compound is a polar, protic-capable organic building block (secondary alcohol + ester + cyclic ether). It dissolves well in many mid-polarity organic solvents.

• Polarity/miscibility (general guidance):
  • Good: ethyl acetate, dichloromethane, chloroform, acetone, acetonitrile, methanol, ethanol, THF.
  • Moderate: toluene, MTBE, CPME.
  • Limited: aliphatic hydrocarbons (hexanes/heptane) unless co-solvent is used.
• Selection by task:
  • NMR: CDCl3 typically affords sharp signals; DMSO‑d6 useful when hydrogen-bonding broadens OH.
  • Chromatography: Normal-phase silica with EtOAc/hexanes or DCM/MeOH gradients is typical; the α‑OH may cause tailing—add 0.1–1% Et3N to the eluent if needed.
  • Reactions: For acylations/protections, use DCM, EtOAc, or MeCN. For metal-catalyzed steps, dry Et2O/THF/CPME may be chosen depending on catalyst compatibility.
• Comparison note (general):
  • Relative to less polar esters, the α‑OH increases polarity and hydrogen bonding; choose slightly more polar eluents/solvents to maintain solubility and manageable viscosity.

Storage and Reconstitution

• Storage conditions (from Product Data): Room temperature.
• Shipped in: Not specified for this item.
• Physical form/appearance: Not specified for this item; refer to CoA/Spec Sheet.

General guidance for α-hydroxy esters (informational):

• Store tightly capped under inert atmosphere if long-term storage is anticipated, especially for moisture- and air-sensitive transformations downstream.
• Avoid prolonged exposure to strong light and heat. Keep container dry to minimize slow hydrolysis or transesterification.
• If solid at room temperature, warm gently to redissolve before use; if liquid, use dry syringes/pipettes to avoid introducing moisture.
• Reconstitution: Not applicable; use as supplied. If dilution is needed, choose a dry, compatible solvent (e.g., DCM, EtOAc, MeOH, THF) based on your intended application.
• Stability: No specific shelf-life data are provided for this item; refer to CoA/Spec Sheet and SDS. Inspect periodically by NMR/GC/HPLC if stored for extended periods.

Structure and Identity

Ethyl 2-hydroxy-2-(oxolan-3-yl)acetate is an α-hydroxy ester bearing a tetrahydrofuran (oxolane) ring at the α-carbon of an ethyl glycolate framework.

• Product identifiers (from Product Data)
  • CAS: 221546-88-9
  • CID: 15415399
  • InChIKey: 460082 (as provided)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Structure description (general/literature):
  • Core motif: α-hydroxy acetate (glycolate) ethyl ester.
  • Substituent: oxolan-3-yl (tetrahydrofuran-3-yl) bound to the α-carbon (C-2) that also bears the hydroxyl group.
  • Functional groups: secondary alcohol (α-OH), ethyl ester (–CO2Et), cyclic ether (tetrahydrofuran).
  • Stereochemistry: the α-carbon is a stereogenic center when unsubstituted by symmetry; material may be racemic unless specified (no stereochemical information provided for this item).
• Empirical composition (literature/computed, not item-specific):
  • Typical molecular formula: ~C8H14O4 (literature/computed from name)
  • Approximate molecular weight: ~174.19 g/mol (literature/computed)
• 2D structural narrative: an ethyl ester carbonyl (–C(=O)OCH2CH3) is α-substituted by a carbon bearing a hydroxyl (–OH) and a 3-substituted tetrahydrofuran ring; the THF ring contributes a cyclic ether oxygen within a five-membered ring.

Synthetic Utility

Key functional elements and reactivity handles:

• Secondary alcohol (α‑OH):
  • Selective protection (silyl, carbonate, acyl) to control reactivity.
  • Activation (e.g., as mesylate/tosylate or via Mitsunobu) for substitution, enabling C–N, C–O, or C–S bond formation with inversion when applicable.
  • Oxidation to α‑keto ester to unlock enolate chemistry and nucleophilic additions.
• Ester (–CO2Et):
  • Amenable to saponification (to acid), transesterification (ROH/H+ or base-catalyzed), and reduction to the corresponding diol/aldehyde (DIBAL-H, LiAlH4—choose conditions to tune chemoselectivity).
• THF ring:
  • Stable cyclic ether that can undergo regioselective ring-opening under strong acid or with nucleophiles, providing ω‑hydroxy derivatives.
  • Serves as an embedded protecting group for a 1,4-diol equivalent in synthetic sequences.

Retrosynthetic value:

• Disconnection through the Cα–THF bond suggests alkylation of a glycolate equivalent with a 3‑substituted THF electrophile or radical coupling using a THF-derived radical with a glycolate acceptor (photoredox literature).
• Alternatively, assemble by nucleophilic addition of a THF-3-yl organometallic (carefully chosen to avoid ester reduction) to a glyoxylate derivative, followed by quench to furnish the α‑OH stereocenter.

Target Specificity

Not applicable. This product is a small-molecule chemical reagent and does not have biological target specificity, epitopes, or isotypes. No antibody or bioreagent attributes are associated with this item.