Ethyl acetate - UPSS grade,Single metal impurity ≤ 0.1ppb , CAS No.141-78-6

CAS: 141-78-6 Cat. No.: E1523832 Summenformel: C₄H₈O₂ Molekulargewicht: 88.11 Beilstein Registry Number: 506104 EG-Nummer: 205-500-4

QUALITÄT & REINHEIT UPSS grade, Single metal impurity ≤ 0.1ppb

Storage

Room temperature

Shipped In

FedEx DG Service

Spezifikationen

Spezifikationen & Reinheit

UPSS grade,Single metal impurity ≤ 0.1ppb

Storage

Room temperature

Verschickt in

FedEx DG Service

Note

UPSS-Klasse

Namen und Kennungen

Kanonisches Lächeln

CCOC(=O)C

IUPAC Name

ethyl acetate

InChIKey

XEKOWRVHYACXOJ-UHFFFAOYSA-N

INCHI

1S/C4H8O2/c1-3-6-4(2)5/h3H2,1-2H3

Isomere SMILES

CCOC(=O)C

WGK Deutschland

1

RTECS

AH5425000

UN-Nummer

1173

Verpackungsgruppe

II

Molekulargewicht

88.11

Beilstein

506104

Reaxy-Rn

506104

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=506104&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Klasse Carboxylic acids and derivatives
      • Subclass Carboxylic acid derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Klasse: Carboxylic acids and derivatives
• Subclass: Carboxylic acid derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Carboxylic acid esters
• Alternative Parents: Monocarboxylic acids and derivatives Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Carboxylic acid ester - Monocarboxylic acid or derivatives - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aliphatic acyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group).
• External Descriptors: a small molecule

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

• Brechungsindex: 1.3720
• Flammpunkt (°C): -3°C
• Siedepunkt (°C): 76.5-77.5 °C
• Schmelzpunkt (°C): -84 °C
• Molekulargewicht: 88.110 g/mol
• XLogP3: 0.700
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 88.0524 Da
• Monoisotopic Mass: 88.0524 Da
• Topological Polar Surface Area: 26.300 Ų
• Heavy Atom Count: 6
• Formal Charge: 0
• Complexity: 49.500
• 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 (e.g., WB, IHC, IF, FC) are applicable to a neat solvent. For laboratory use, typical procedures involve:

• Solvent drying: Add activated 3 Å molecular sieves (10–20% w/v) and allow to stand overnight; verify dryness by Karl Fischer (general technique).
• Flash chromatography: Start with 0–30% ethyl acetate in hexanes for nonpolar organics; adjust gradient based on TLC Rf (general guideline).
• Liquid–liquid extraction: Combine with aqueous phase, mix, vent frequently, separate layers, dry over Na2SO4/MgSO4, and concentrate (general workflow).

Item-specific tested applications are not provided for this product; consult your method SOPs and the product CoA/SDS for any constraints.

Biological Roles

Item-specific biological testing or roles: Not specified for this item; for research use only.

General biochemical context (literature):

• Metabolic fate: Ethyl acetate can be hydrolyzed by esterases to ethanol and acetic acid. In microbial and yeast metabolism, analogous short-chain esters are produced/consumed as part of flavor/aroma pathways.
• Occurrence: Trace levels arise in fermented beverages and natural products as a volatile ester contributing fruity notes; such occurrence is incidental rather than functional in biology.
• Toxicology overview: Exhibits low acute toxicity relative to many organic solvents, but vapor can cause CNS depression at high concentrations; eye/respiratory irritation possible (consult SDS for authoritative data).
• Biodegradation: Readily biodegradable under aerobic conditions; hydrolysis contributes to environmental attenuation (literature).

Lab interface with biology (general practice):

• Cell and protein work: Usually avoided as a component of biological buffers due to volatility and potential to denature proteins; however, it is frequently used to extract small molecules from biological matrices (e.g., plasma/urine) for LC–MS workflows.
• Enzymology: Solvent tolerance varies by enzyme; residual EtOAc is typically removed prior to assays to prevent activity loss.

Note: No medical or clinical claims are made. This product is intended for research laboratory use only.

Buffer Applications

Ethyl acetate is not a buffering reagent and is not used to prepare aqueous buffer systems. Due to its volatility and only partial water miscibility, it is generally unsuitable for direct use in biological buffers or electrophoresis media.

Practical guidance (general):

• For extractions from buffered aqueous solutions, ethyl acetate can serve as the organic phase. Adjust ionic strength (e.g., saturate with NaCl) and pH to favor partitioning of neutral species; remove residual solvent thoroughly before downstream aqueous assays.
• For actual buffer preparation, select appropriate buffering agents (e.g., phosphate, Tris, HEPES) according to the desired pH range.

Green Alternatives

Ethyl acetate itself is widely regarded as a greener solvent (readily biodegradable, relatively low toxicity, derivable from bio-ethanol and acetic acid). That said, solvent choice is context-dependent.

Comparison (general, literature-based):

• Ethyl acetate vs dichloromethane (DCM)
  • Greenness: EtOAc favored (non-halogenated, lower toxicity, lower persistence).
  • Performance: DCM offers higher density and stronger solvency for very nonpolar analytes; EtOAc preferred when density or chlorinated waste are concerns.
• Ethyl acetate vs acetone
  • Greenness: Both considered relatively green; acetone has full water miscibility and higher vapor pressure; EtOAc less volatile and only partially water-miscible—often advantageous in extractions.
• Ethyl acetate vs 2-MeTHF/CPME
  • MeTHF/CPME: Also green choices with low peroxide tendency (CPME) and good hydrophobicity; they offer water immiscibility and broader temperature windows. EtOAc offers simpler odor profile and broader availability.

Typical trade-offs:

• Boiling point and removal energy: EtOAc (bp ~77 °C) vs DCM (bp ~40 °C). EtOAc may require slightly more energy to remove but avoids chlorinated emissions.
• Aqueous fate: EtOAc hydrolyzes to ethanol and acetic acid; manageable in waste treatment (literature).

Green practice tips (general):

• Recycle via fractional distillation where feasible; monitor for hydrolysis by GC.
• Optimize chromatography gradients to minimize solvent consumption (e.g., tighter polarity windows with hexanes/EtOAc).

Pharmaceutical Uses

Item-specific pharmacopeial status or excipient grade: Not specified for this item; refer to CoA/Spec Sheet.

General information (literature and industry practice; not clinical):

• Role: Common process solvent for synthesis steps, crystallization, and purification; also used as a coating solvent for film-formers in solid oral dosage manufacture.
• Regulatory status: Ethyl acetate is listed in major pharmacopeias (e.g., USP–NF, Ph. Eur.) as a reagent/solvent; acceptance criteria and residual solvent limits in drug products follow ICH Q3C (Class 3) guidance.
• Advantages: Non-halogenated, relatively low toxicity, easy removal, and favorable environmental profile compared to chlorinated solvents.
• Considerations: Potential for hydrolysis to acetic acid/ethanol; monitor acidity and residual levels by GC. Ensure low nonvolatile residue and controlled water content for sensitive crystallizations.

Manufacturing practice (general):

• Often paired with heptane/hexane as antisolvent systems for crystallization control.
• Suitable for wet granulation solvent systems when polymer/API solubility aligns; ensure appropriate LEL controls and explosion-proof equipment.
• For coatings, check polymer compatibility and drying kinetics; bp ~77 °C affords balanced evaporation and film formation.

Physical Properties

Item-specific specifications: Not specified for this item; refer to CoA/Spec Sheet for any tested values (e.g., water content, UV cutoff, metals, stabilizers).

Literature/reference properties (typical values; not certification for this lot):

• Appearance: Colorless, volatile liquid with characteristic fruity odor (literature)
• Boiling point: ~77.1 °C at 1 atm (literature)
• Melting point: ~−83.6 °C (literature)
• Density: ~0.897–0.902 g·mL−1 at 20 °C (literature)
• Refractive index: nD20 ~1.371–1.372 (literature)
• Vapor pressure: ~73–100 mmHg at 20 °C (literature ranges reported)
• Flash point: about −4 °C (closed cup) (literature)
• Autoignition temperature: ~427 °C (literature)
• Dielectric constant (20–25 °C): ~6.0–6.1 (literature)
• Viscosity (25 °C): ~0.45 mPa·s (literature)
• Water solubility: ~8–10 g per 100 g H2O at 20–25 °C; exhibits mutual partial miscibility (literature)
• Miscibility: Miscible with many organics (alcohols, ethers, ketones, aromatics); limited with alkanes at low temperature (literature)
• Partitioning: Moderately polar; commonly used as the polar component in hexanes/EtOAc normal-phase systems (literature)

Notes for practice (general):

• Hygroscopicity: Limited; nevertheless, absorbs some moisture on standing—dry over 3 Å molecular sieves for water-sensitive work (general guidance).
• Azeotropy: Forms a minimum-boiling azeotrope with water (literature); useful for water removal in certain workflows.

Quality and Grades

• Item-specific grade: UPSS grade (as provided). Detailed acceptance criteria (e.g., purity assay, moisture, acidity, UV absorbance profile, metals) are not specified for this item; refer to CoA/Spec Sheet.

Context and guidance (general):

• Solvent grades vary widely (technical, reagent, ACS/AR, HPLC/spectroscopic, anhydrous, inhibitor-stabilized, etc.). Higher grades typically control purity, residual water, acidity/alkalinity, and UV background to support sensitive analytical or synthetic applications.
• For chromatography, low UV absorbance and low nonvolatile residue are essential; for moisture-sensitive synthesis, Karl Fischer water content and conductivity/acidity specifications are critical.

Working implications for ethyl acetate (general):

• If using for LC or UV-based analytics, confirm the UV cutoff and nonvolatile residue on the CoA.
• For water-sensitive applications (e.g., certain organometallics or acid chlorides), verify water content and consider drying over 3 Å sieves prior to use, even for high-grade material.
• Trace acidity in ethyl acetate can influence base-catalyzed reactions or silica gel chromatography; check acidity specs or pre-treat with basic alumina if needed (general technique).

Documentation:

• For this specific catalog item, rely on the lot-specific CoA/SDS for exact grade definitions and parameters. Where critical, perform incoming QC (e.g., GC purity check, KF moisture, UV scan) aligned to your method requirements.

Reaction and Applications

General application domains for ethyl acetate (literature; solvent use unless stated otherwise):

• Chromatography: Widely used with hexanes/heptane in normal-phase flash and prep LC. Adjustable polarity enables fine elution control; often less streaking than with acetone.
• Extraction and workup: Favored as an organic phase for quenching reactions and extracting products from aqueous media. Partial miscibility with water can assist phase disengagement after salt addition (salting out).
• Reaction solvent: Suitable for mild to moderate-temperature transformations (bp ~77 °C). Frequently used in acylations, condensations, and metal-catalyzed couplings that tolerate esters.
• Crystallization/recrystallization: Acts as an intermediate-polarity solvent either neat or in mixtures (e.g., EtOAc/hexanes or EtOAc/ethanol) to optimize solubility curves.

Reactivity considerations (general):

• Stability: Generally stable toward neutral conditions; susceptible to base-catalyzed saponification and acid/base-catalyzed transesterification/hydrolysis.
• Nucleophiles: Strong nucleophiles (alkoxides, amines under forcing conditions) can attack the ester, potentially consuming solvent.
• Coordination: Weakly coordinating; less likely to complex metal centers compared to ethers or amides—beneficial for catalysis requiring open coordination sites.

Practical tips:

• Drying: 3 Å molecular sieves provide effective drying; avoid prolonged contact with strong bases.
• Degassing: Standard sparging or freeze–pump–thaw if oxygen-sensitive reactions are performed.
• Compatibility: Avoid with reagents that react with esters (e.g., LiAlH4, strong alkoxides) unless solvent consumption is acceptable.

Manufacturer applications: Not specified in the Product Data for this item; typical uses above reflect common practice.

Reaction Conditions

The following are general, literature-based guidelines for using ethyl acetate as a solvent; they are not specifications for this product.

• Temperature window: −20 °C to reflux (~77 °C) commonly employed. For higher-temperature needs, select higher-bp solvents.
• Drying and atmosphere: Dry over 3 Å sieves to ≤ few hundred ppm water (target per application). Use inert atmosphere for air/moisture-sensitive reagents.
• Bases and acids: Use mild bases (e.g., Na2CO3, K2CO3) and mild acids; strong bases (alkoxides, hydroxide at high temp) accelerate saponification. Acidic silica can introduce acetate formation during chromatography—pre-neutralize if problematic.
• Catalysis: Compatible with Pd, Ni, Cu catalysis under neutral to mildly basic conditions; low coordinating ability helps maintain active sites. Monitor for ester exchange with alcohol additives.
• Workup/extraction: For aqueous quench, add brine to reduce mutual solubility and improve phase separation. Wash organic extracts with saturated NaHCO3 to remove trace acetic acid if formed.
• Removal: Rotary evaporation at 30–40 °C bath under reduced pressure is effective; co-evaporate with heptane to dry residues.
• Peroxide concerns: Esters like EtOAc are not strong peroxide formers; routine testing typically unnecessary, but follow institutional SOPs.

Expected outcomes: Many condensations, acylations, and metal-catalyzed couplings report typical yields comparable to DCM/THF systems when substrates are soluble; always optimize concentration and base for your specific transformation.

Safety and Handling

Item-specific safety fields provided: Signal word, H-statements, GHS classification, pictograms are not specified for this item; refer to the product SDS for authoritative hazard and precautionary statements.

General GHS classification for ethyl acetate (literature; not item-specific):

• Flam. Liq. 2; Eye Irrit. 2A; STOT SE 3 (narcotic effects)
• Typical pictograms: GHS02 (flame), GHS07 (exclamation)
• Common H-statements (literature): H225 Highly flammable liquid and vapor; H319 Causes serious eye irritation; H336 May cause drowsiness or dizziness.

Handling and PPE (general best practices):

• Use in a well-ventilated fume hood; avoid inhalation of vapors.
• Wear safety glasses or splash goggles, lab coat, and appropriate nitrile gloves.
• Keep away from heat/sparks/open flames/hot surfaces. Use only non-sparking tools; ground/bond containers when transferring.

Incompatibilities and stability (general):

• Incompatible with strong oxidizers, strong bases (saponification), and strong acids (hydrolysis).
• Eases hydrolysis in presence of moisture and acid/base catalysts; store in tightly closed container.

First aid overview (general):

• Inhalation: Move to fresh air; seek medical attention if symptoms persist.
• Eye/skin contact: Rinse cautiously with water for several minutes; remove contaminated clothing.
• Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.

Fire response (general):

• Use alcohol-resistant foam, dry chemical, or CO2. Water spray may be used to cool containers.

Always consult the SDS specific to this item for definitive safety information.

Solvent Selection

Role and polarity (general):

• Ethyl acetate is a moderately polar, aprotic ester solvent with dielectric constant ~6 (literature). It bridges the gap between nonpolar hydrocarbons and polar ketones/alcohols.

Miscibility profile (general):

• Miscible with: alcohols, ethers, acetone, many aromatics; partially miscible with water; mixtures with alkanes/hexanes are fully miscible and tunable for normal-phase chromatography.

When to choose ethyl acetate (general):

• Normal-phase chromatography: Commonly paired with hexanes or heptane; gradients of 5–50% EtOAc effectively elute many polar organics.
• Liquid–liquid extraction: Useful counter-solvent versus aqueous phases; moderate polarity helps extract esters, amides, and moderately polar heterocycles while minimizing emulsion vs. DCM in some systems.
• Reaction medium: Suitable for many condensation and acylation reactions where a mild, non-basic solvent is desired.
• Workup: Convenient due to low boiling point (~77 °C) and relatively benign safety profile compared to chlorinated solvents.

Comparison (general; literature perspectives):

• Versus dichloromethane: Less dense, less toxic, higher bp, greener profile; however, less powerful for dissolving very nonpolar substrates.
• Versus acetone: Lower polarity; less miscible with water, which can be advantageous in extractions.
• Versus 2-MeTHF/THF: Less coordinating than ethers; often safer and greener than THF for many extractions/purifications.

Practical tips:

• Dry over 3 Å sieves for water-sensitive chemistry.
• For silica chromatography, ensure low-peroxide content is not typically a concern (esters seldom form peroxides), but always verify solvent quality per application.

Storage and Reconstitution

• Item-specific storage: Room temperature (as provided). Keep container tightly closed in a cool, well-ventilated area.
• Shipping: FedEx DG Service (as provided). Handle as a flammable liquid per Dangerous Goods regulations.
• Reconstitution: Not applicable—supplied as a ready-to-use liquid solvent.

General storage guidance for ethyl acetate:

• Segregate from oxidizers, strong acids/bases, and ignition sources. Use flammable cabinets for bulk storage.
• Minimize headspace and moisture ingress to limit hydrolysis; use septum-sealed bottles or add drying tubes when frequent access is required.
• For high-purity applications, consider storing over activated 3 Å molecular sieves; replace/roast sieves periodically.
• Shelf life: Monitor for increases in acidity or odor changes (hydrolysis). Confirm suitability by quick GC and/or KF before critical use.

Freeze–thaw: Not applicable; avoid refrigeration below flash point concerns only for vapors—ambient storage is appropriate per SDS unless otherwise specified on the CoA.

Structure and Identity

Brief overview: Ethyl acetate is a simple aliphatic ester (acetic acid ethyl ester), widely used as a polar, aprotic, volatile organic solvent.

• Item-specific identifiers (from Product Data)

  • SKU: E1523832
  • Product name: Ethyl acetate
  • CAS: 141-78-6
  • CID: 8857
  • Grade: UPSS grade
  • Storage: Room temperature
  • Shipped in: FedEx DG Service
  • InChIKey: 415824 (as provided)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/registry information (chemistry reference; not item-specific)

  • Preferred IUPAC name: Ethyl acetate
  • Molecular formula (literature): C4H8O2
  • Molecular weight (literature): 88.11 g/mol
  • SMILES (literature): CCOC(=O)C
  • InChIKey (literature): XEKOWRUJDYBDME-UHFFFAOYSA-N

• Structural features (general)

  • Functional groups: One carboxylate ester (–CO2–) linking an acetyl moiety (CH3–CO–) to an ethyl group (–CH2CH3).
  • Saturation/aromaticity: Fully aliphatic, no rings, no heteroatoms beyond two oxygens.
  • Donor/acceptor profile: No H-bond donors; two H-bond acceptor sites (carbonyl O and alkoxy O).
  • 2D description in words: A carbonyl carbon double-bonded to oxygen and single-bonded to a methyl (acetyl end) and to an alkoxy oxygen bearing an ethyl substituent.
  • Polarity: Moderately polar aprotic; dipole oriented across the ester carbonyl.

Synthetic Utility

Functional profile (general):

• Solvent: Moderately polar, aprotic; weakly coordinating—compatible with many catalysts and electrophiles.
• Reactivity limits: Subject to base- or acid-catalyzed hydrolysis and transesterification; strong nucleophiles may attack the solvent (ester cleavage).

Use cases (literature):

• Acylation/condensation media: Effective for reactions involving acid chlorides/anhydrides and neutral to mildly basic conditions.
• Catalysis: Suitable for many transition-metal-catalyzed couplings (e.g., Suzuki–Miyaura, Heck) when substrates and bases tolerate ester media.
• Workup/extraction: Preferred organic layer for isolating products from aqueous reaction mixtures; salting-out strategies enhance phase split.
• Crystallization engineering: EtOAc/hexane or EtOAc/toluene mixtures tune solvency and morphology for API intermediates.

Operational guidance:

• Drying: Use 3 Å sieves; avoid basic drying agents that could promote saponification.
• Acid/base sensitivity: Limit exposure to strong bases (e.g., >0.5 M alkoxides) or strong acids at elevated temperature to prevent solvent consumption.
• Purification compatibility: Ideal for normal-phase flash chromatography; monitor eluotropic strength to prevent co-elution of impurities.

Retrosynthetic note:

• While primarily a solvent, ethyl acetate can serve as a benign acyl donor under specific catalytic conditions (e.g., borrowing-ester strategies), but this is specialized and not typical for routine synthesis.

Target Specificity

Not applicable. This product is a neat solvent (ethyl acetate), not a biological targeting reagent (e.g., antibody, ligand, probe). No antigen/epitope, clone, isotype, or species reactivity data apply.