Ethyl 4-ethoxybutyrate - ≥97% , CAS No.26448-91-9

CAS: 26448-91-9 Cat. No.: E341712 Fórmula: C₂H₅O(CH₂)₃CO₂C₂H₅ Peso molecular: 160.21

GRADE & PURITY ≥97%

Synonyms

Ethyl 4-ethoxybutyrate | DTXSID10403149 | AKOS015894336 | J-016430 | Ethyl 4-ethoxybutyrate, 98% | 4-ethoxy-butyric acid ethyl ester | Ethyl 4-ethoxybutanoate | SCHEMBL2943131 | NQYKGEPHDRUFJL-UHFFFAOYSA-N | starbld0032795

Storage

Room temperature

Shipped In

Normal

Descripción general

Product Describtion:

Ethyl 4-ethoxybutyrate, also known as ethyl 4-ethoxybutanoate, is an aliphatic ester. Its enthalpy of vaporization at boiling point (457.65K) has been reported to be 39.830kjoule/mol.

Specifications

Sinónimos

Ethyl 4-ethoxybutyrate | DTXSID10403149 | AKOS015894336 | J-016430 | Ethyl 4-ethoxybutyrate, 98% | 4-ethoxy-butyric acid ethyl ester | Ethyl 4-ethoxybutanoate | SCHEMBL2943131 | NQYKGEPHDRUFJL-UHFFFAOYSA-N | starbld0032795

Especificaciones y pureza

≥97%

Condiciones de almacenamiento de almacenamiento

Room temperature

Enviado en

Normal

Pureza

≥97%

Nombres e identificadores

• Pubchem Sid: 504763016
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504763016
• Sonrisas canónicas: CCOCCCC(=O)OCC
• IUPAC Name: ethyl 4-ethoxybutanoate
• InChIKey: NQYKGEPHDRUFJL-UHFFFAOYSA-N
• INCHI: 1S/C8H16O3/c1-3-10-7-5-6-8(9)11-4-2/h3-7H2,1-2H3
• Isómeros SMILES: CCOCCCC(=O)OCC
• WGK Alemania: 3
• Peso molecular: 160.21
• Reaxy-Rn: 1756824
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1756824&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Clase Fatty Acyls
      • Subclass Fatty acid esters

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Clase: Fatty Acyls
• Subclass: Fatty acid esters
• Intermediate Tree Nodes: Not available
• Direct Parent: Fatty acid esters
• Alternative Parents: Carboxylic acid esters Monocarboxylic acids and derivatives Dialkyl ethers Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Fatty acid ester - Carboxylic acid ester - Monocarboxylic acid or derivatives - Ether - Dialkyl ether - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aliphatic acyclic compound
• Descripción: This compound belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
• 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

• Índice de refracción: 1.413
• Punto de ebullición (°C): 183-186° C at 1013 hPa (Predicted)
• Peso molecular: 160.210 g/mol
• XLogP3: 1.000
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 160.11 Da
• Monoisotopic Mass: 160.11 Da
• Topological Polar Surface Area: 35.500 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 102.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• 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

No assay/application protocols are specified for this item. As a general-purpose organic reagent:

• For hydrolysis or transesterification, see Reaction Conditions for starting parameters and adjust based on your substrate and scale.
• For reductions or couplings, run small-scale scouting experiments first (0.1–1.0 mmol) and monitor by GC/MS or LC–MS.

There are no validated dilutions or controls as would apply to biological reagents.

Biological Roles

This product is a small-molecule ether–ester intended for laboratory chemical synthesis and process research. It is not a biological reagent and does not have defined endogenous roles.

• No known physiological role is associated with Ethyl 4-ethoxybutyrate as such. Any biological interactions would be nonspecific solvent-like effects typical of small, hydrophobic organic esters and ethers.
• If used as a matrix or vehicle in biochemical assays, consider:
  • Solvent tolerance of enzymes or cells (many ester/ether solvents can denature proteins or disrupt membranes above low percentages).
  • Hydrolysis under biological conditions, potentially yielding ethanol and 4-ethoxybutyric acid—rates depend strongly on pH and esterases.

All uses are for research only. Avoid extrapolating any in vitro behavior to physiological or clinical contexts.

Buffer Applications

Not typically applicable. Ethyl 4-ethoxybutyrate is a neutral, non-buffering organic liquid and does not form acid/base buffer systems in water. If used in aqueous workflows, it would serve only as an organic cosolvent at low percentages, which can affect buffer pH and ionic strength indirectly. For true buffering needs, select established systems (e.g., phosphate, HEPES, Tris) appropriate to your target pH and ionic environment.

Green Alternatives

Because Ethyl 4-ethoxybutyrate is often used as a functional reagent rather than a bulk solvent, “greener alternative” discussions should consider the role it plays in your process (medium vs. substrate). If you are using it mainly as a medium/cosolvent, these options may be preferable.

Comparison (general; not product specifications):

• Ethyl acetate

  • Pros: Widely accepted green solvent, low toxicity profile, readily biodegradable, easy recovery due to volatility.
  • Cons: Lacks ether functionality; can participate in base-catalyzed transesterification; lower boiling point can be a drawback for higher-temperature steps.

• 2-Methyltetrahydrofuran (2-MeTHF)

  • Pros: Biomass-derived, good performance in organometallic chemistry, better water tolerance than THF, recyclable.
  • Cons: Ether peroxide risk exists (lower than diethyl ether); different polarity than ester media; may swell certain elastomers.

• Cyclopentyl methyl ether (CPME)

  • Pros: Good hydrophobicity, lower peroxide formation tendency than many ethers, wide liquid range, easy phase separation from water.
  • Cons: Limited availability/price; aromatic impurity control can be necessary for sensitive applications.

• Dimethyl carbonate (DMC) / Ethyl methyl carbonate

  • Pros: Green carbonate esters, good solvency, participate in benign methyl/ethylation and transesterifications.
  • Cons: Different reactivity; may not mimic ether–ester behavior.

Guidance

• If Ethyl 4-ethoxybutyrate is the reaction substrate, a “greener alternative” would be a different synthesis route or protecting-group strategy rather than a solvent swap.
• Evaluate PMI, solvent recyclability, and EHS metrics alongside yield/selectivity when choosing alternatives.

Pharmaceutical Uses

No pharmacopeial grade or excipient designation is provided for this item. This product is offered for research use only.

General formulation context (non-clinical, for process R&D discussions):

• Ether–esters can function as specialty solvents or flavor/aroma components in non-pharmaceutical industries; however, suitability for GMP or human exposure contexts requires rigorous tox/EHS evaluation and compendial compliance that are not established here.
• If exploring as a processing aid in preclinical chemistry:
  • Confirm extractables/leachables with contact materials.
  • Define residual solvent limits per ICH Q3C for any analogous solvent; note that Ethyl 4-ethoxybutyrate is not listed and would require internal safety assessments.

No therapeutic or clinical claims are made or implied.

Physical Properties

Item-specific physicochemical specifications (bp, mp, density, refractive index, water/peroxide/metal limits, UV cutoff) are not provided for this SKU. Always consult the CoA/Spec Sheet for lot-specific values.

Literature/general properties for the neat compound (for planning; not product specifications):

• Phase at ambient conditions: clear, colorless liquid (typical for short-chain, non-branched ether–esters).
• Volatility: moderate; contains a low–moderate boiling ester with an additional ether, suggesting appreciable vapor pressure at room temperature. Use closed systems to minimize loss.
• Solubility profile (qualitative, literature):
  • Miscible with many common organic solvents (e.g., ethers, esters, hydrocarbons, chlorinated solvents, alcohols).
  • Limited solubility in water is expected due to the predominance of hydrophobic alkyl content despite two heteroatoms.
• Polarity: low-to-moderate (ether–ester); suitable as a weakly polar, aprotic medium.
• Hydrogen-bonding: H-bond acceptor (carbonyl and ether O), non-donor.

Practical notes (general):

• Expected to have a refractive index higher than alkanes of similar carbon count (ether/ester increase polarizability), and a density slightly below or near that of water; verify against literature before use in calibrated work.
• Viscosity should be low, enabling easy handling and pipetting.

If precise numeric values are required (bp, density, nD, logP, pKa, dielectric constant), obtain them from authoritative databases or measure under your conditions; do not infer from the above qualitative guidance.

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.

Guidance on common grades you may encounter for ether–ester liquids (general information):

• Technical/industrial grade: Suitable for process development where trace impurities and higher moisture are acceptable. Verify suitability if the compound participates in sensitive steps (e.g., base-catalyzed transesterifications).
• AR/ACS grade: Tighter control of common impurities. Useful for analytical sample prep and general synthesis where batch-to-batch consistency is needed.
• HPLC/GC grade solvents: Defined by low UV absorptivity, low non-volatile residue, and minimal particulates. While Ethyl 4-ethoxybutyrate is primarily a reagent, solvent-grade criteria may be relevant if used as a chromatography mobile-phase modifier or matrix; confirm UV cutoff from literature if critical.
• Water and peroxide limits: Not specified for this item; consult CoA or test in-house where peroxide content or water is critical (e.g., for base-sensitive reactions or distillations).

Stabilizers/inhibitors:

• This product listing does not indicate added stabilizers. If low-peroxide material is required, consider testing/remediation (e.g., alumina/peroxide scavengers) under validated procedures.

Fit-for-purpose tips:

• For nucleophile/base-catalyzed chemistry (transesterification, amidation), ensure acid number and water content meet your process window.
• For kinetic studies or spectroscopic work, request/verify UV-vis background and purity profile (GC/FID, GC–MS, or 1H/13C NMR).

Reaction and Applications

This compound combines an ethyl ester and a terminal ethoxy substituent, offering both reactivity (at the ester) and relative inertness (at the ether) under many conditions. Representative application spaces (literature/general):

• Ester transformations

  • Hydrolysis: Acid- or base-catalyzed hydrolysis to 4-ethoxybutyric acid. Base saponification is fast in MeOH/H2O; acid hydrolysis avoids transesterification.
  • Transesterification: Alcoholysis under acid (e.g., catalytic TsOH) or base (alkoxide) to give alternative alkyl esters of 4-ethoxybutyric acid. Remove ethanol by azeotropic distillation to drive equilibrium.
  • Amidation: Activation (e.g., mixed anhydride, CDI) or direct aminolysis under forcing conditions to access 4-ethoxybutyramides.
  • Reduction: LiAlH4, DIBAL-H, or catalytic hydrogenation (with appropriate catalysts) can reduce the ester to 4-ethoxybutanol; partial reduction to the aldehyde may be achieved with DIBAL-H at low temperature.

• Ether considerations

  • The terminal ethoxy is generally robust to bases and many nucleophiles but can be cleaved by strong acids (HI, HBr) or Lewis acids (e.g., BBr3 for aryl ethers; aliphatic ether cleavage requires harsher HX).
  • Oxidative stability: Ethers can form peroxides on storage; employ peroxide testing for long-held stocks and avoid concentrating to dryness.

• Strategic use

  • As a masked 4-hydroxybutyl synthon: Post-cleavage of the ethoxy (via acidic conditions) yields a 4-hydroxyl functionality distal to the ester, enabling intramolecular cyclizations or further derivatization.
  • Spacer chemistry: The three-methylene tether between carbonyl and ether offers conformational flexibility for linking strategies in small-molecule probe synthesis.

Practical tips

• Drying: If water-sensitive steps are planned, dry over MgSO4 or molecular sieves; verify water by Karl Fischer when critical.
• Catalyst compatibility: Avoid strong Bronsted acids if ether integrity must be retained; choose milder acid catalysts for transesterification.

Reaction Conditions

General literature-style guidance for common transformations of Ethyl 4-ethoxybutyrate (plan experiments and validate locally; not product specifications):

• Saponification to 4-ethoxybutyric acid

  • Typical: 1–2 equiv NaOH or KOH in EtOH/H2O (1:1 to 4:1), 20–50 °C, 1–6 h. Workup by acidification and extraction. Near-quantitative conversions are common for simple ethyl esters.

• Acid-catalyzed transesterification

  • Catalyst: p-toluenesulfonic acid (1–5 mol%) or H2SO4 (0.5–2 mol%). Alcohol (5–10 equiv), reflux in Dean–Stark with toluene or neat at the alcohol bp. 2–12 h, monitor by GC.

• Aminolysis to amide

  • Neat or in toluene/THF, primary amine (2–5 equiv), 80–120 °C; or activate as acid chloride (SOCl2, DMF cat.) then couple with amine base (Et3N, 0 °C→rt→reflux). Typical isolated yields for activated couplings: 70–95% (substrate-dependent).

• Reduction

  • DIBAL-H (1.1–1.5 equiv) in toluene or CH2Cl2 at –78 to –50 °C, 0.5–2 h to aldehyde; quench with MeOH then Rochelle’s salt. Over-reduction yields the alcohol.
  • LiAlH4 (1.5–2.5 equiv) in THF/Et2O, 0 °C→reflux, 1–3 h to 4-ethoxybutanol; careful quench.

• Ether cleavage (to unveil 4-hydroxybutyrate derivatives)

  • HI or HBr (48% aq or conc.), reflux hours; forms EtI/EtBr and corresponding alcohol. Competing ester hydrolysis possible—optimize acid strength/solvent.

• Drying/handling

  • Dry over molecular sieves (3A/4A) or MgSO4. Degas if using in moisture/oxygen-sensitive steps. Test for peroxides before distillation, discard residues.

All parameters above are generalized from analogous ester/ether literature and should be optimized for scale, equipment, and desired selectivity.

Safety and Handling

Item-specific GHS and hazard statements are not provided in the Product Data. Refer to the SDS for authoritative classification, first-aid, and regulatory information for this material and your jurisdiction.

General laboratory safety considerations for aliphatic ether–esters (non-binding guidance):

• Flammability: Treat as a combustible/flammable organic liquid. Keep away from ignition sources, hot surfaces, and sparks. Use only in well-ventilated areas or a fume hood.
• Peroxide formation: Ethers can slowly form peroxides upon prolonged exposure to air and light. While alkyl aryl/dialkyl ethers are most prone, even simple ethoxy motifs may oxidize over time. Store in tightly closed containers; consider periodic peroxide testing for long-stored material. Do not distill to dryness.
• Stability/incompatibilities: Avoid strong acids (acidic cleavage of ethers possible, especially HX), strong bases (saponification/transesterification), and strong oxidizers. Moisture can promote ester hydrolysis under acidic/basic conditions.
• PPE: Safety glasses, lab coat, and appropriate chemically resistant gloves (e.g., nitrile). Avoid skin/eye contact and inhalation of vapors or aerosols.
• Handling: Use secondary containment. Ground/bond during transfer if flammability is confirmed by SDS. Employ spill trays and absorbents suitable for organic liquids.
• First aid (overview; defer to SDS): Move to fresh air after inhalation; rinse skin with soap/water after contact; flush eyes with water for ≥15 min; seek medical attention if symptoms persist. Ingestion: rinse mouth; do not induce vomiting unless directed by medical personnel.

Storage and shipping (item-specific):

• Storage Conditions: Room temperature (per Product Data).
• Shipped in: Normal conditions (per Product Data).

Solvent Selection

Applicability note: Ethyl 4-ethoxybutyrate is primarily a functional reagent/building block (ester with an ether tail), not a commodity solvent. However, its low-to-moderate polarity and aprotic character can make it serviceable as a specialty medium or cosolvent in specific synthesis scenarios.

General solvent characteristics (literature/general; not item-specific specifications):

• Polarity: weakly to moderately polar aprotic; supports ionic bases/nucleophiles less effectively than dipolar aprotics (DMF/DMSO), but better than pure hydrocarbons.
• Miscibility: broadly miscible with common organic solvents (ethers, esters, aromatics, chlorinateds, many alcohols). Limited water miscibility is expected.
• Coordination: carbonyl oxygen offers weak Lewis basicity; ether oxygen adds modest donor capacity. Not a strong ligand compared with ethers like THF.

When to consider using it:

• As an in situ reagent–medium where the reagent function (ester) is later consumed (e.g., transesterification screens) while maintaining ether compatibility.
• As an organic phase for extractions when a slightly heavier-than-typical ester phase behavior is desired; verify density before process use.

Alternatives comparison (general):

• Ethyl acetate: greener, widely available, higher volatility, stronger ester character; no ether moiety.
• 2-MeTHF/CPME: greener ethers with low peroxide tendency (CPME) and good water tolerance (2-MeTHF); lack ester functionality that can complicate basic media.
• Toluene/Hexanes: less polar, inert; better for hydrophobic substrates where donor interactions are undesirable.

Storage and Reconstitution

• Storage (item-specific): Room temperature (per Product Data). Protect from moisture, light, and ignition sources. Store tightly closed under air or inert gas as appropriate for your workflow.
• Shipping (item-specific): Normal conditions (per Product Data).
• Container: Use amber glass where possible to limit photo-oxidation; employ PTFE-lined caps to reduce permeation.
• Shelf life: Not specified for this item; refer to CoA/Spec Sheet. For long-term storage, consider periodic GC check for purity and qualitative peroxide screening if stored for extended periods.
• Reconstitution: Not applicable—supplied as a neat liquid. If a solution is required, prepare fresh in a compatible dry solvent (e.g., toluene, THF, EtOAc) and label with concentration and date.
• Freeze–thaw: Not applicable.
• Disposal: Collect as halogen-free organic waste unless your process introduces halogenated contaminants. Follow institutional and local regulations.

Structure and Identity

Ethyl 4-ethoxybutyrate is an aliphatic mixed functional molecule featuring both an ester and an ether in a four-carbon backbone. This dual functionality makes it a useful, relatively inert organic medium or convertible building block under standard laboratory conditions.

• Item-specific identifiers (from Product Data)

  • CAS: 26448-91-9
  • CID: 4424983 (PubChem)
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/computed identifiers (for reference; not item specifications)

  • Preferred SMILES (literature): CCOC(=O)CCCOCC
  • Molecular formula (computed from structure): C8H16O3
  • Formula weight (computed): 160.21 g/mol

• Structural features (general chemistry description)

  • Functional groups: one terminal ethyl ester (–CO2Et) and one primary ethyl ether (–O–CH2CH3) at the ω-position (4-position) of the butyl chain.
  • Linear, flexible C4 polymethylene spacer between carbonyl and ether oxygen (–C(=O)–CH2–CH2–CH2–O–).
  • No rings, no stereocenters, no conjugation; a single degree of unsaturation from the ester carbonyl.

• 2D description in words

  • Ethyl ester of 4-ethoxybutyric acid: EtO–C(=O)–CH2–CH2–CH2–O–Et. The carbonyl carbon connects to an ethoxy leaving group; the distal terminus of the butyl chain is capped by an ethoxy substituent.

Synthetic Utility

Ethyl 4-ethoxybutyrate is a versatile bifunctional molecule enabling orthogonal manipulations at the ester and ether sites.

• Ester-centric chemistry

  • Nucleophilic substitutions via activation: Convert to acid chloride (SOCl2, oxalyl chloride) or mixed anhydrides to enable coupling with amines/alkoxides (amide/ester synthesis) while preserving the distal ether.
  • Reductive routes: DIBAL-H reduction to the corresponding aldehyde at low temperature (–78 to –40 °C, literature generality), enabling subsequent aldol/Grignard additions; full reduction to 4-ethoxybutanol with LiAlH4 or catalytic hydrogenation in the presence of alcohol-tolerant catalysts.
  • Enolate chemistry of related derivatives: The parent ester can be α-deprotonated (LDA, LHMDS) after appropriate protection of the ether (if needed) to introduce branching at the α-position.

• Ether-centric chemistry

  • Chemoselective cleavage of the terminal ethoxy under strong protic conditions (HI/HBr) to unmask a 4-hydroxyl butyl ester, providing a handle for intramolecular cyclizations (e.g., to tetrahydrofuran derivatives after subsequent transformations) or for further O-alkylation.
  • Oxidation at the terminal ethyl side chain is generally not favored; the ether is best considered a masked alcohol.

• Linker/scaffold use

  • The three-methylene spacer between carbonyl and oxygen provides a flexible handle in conjugation strategies where spacing from an acid-derived junction is desired.

Note: Choose conditions that preserve the non-target functionality (e.g., neutral or mildly basic media to protect the ether; non-nucleophilic bases to limit transesterification).

Target Specificity

Not applicable. This product is a small-molecule chemical reagent and does not possess biological target specificity (no antigen/epitope, clone, or isotype information).