Ethyl acetate - UPSSS grade,Single metal impurity ≤ 0.01ppb , CAS No.141-78-6

CAS: 141-78-6 Cat. No.: E1523836 분자식: C₄H₈O₂ 분자량: 88.11 Beilstein Registry Number: 506104 EC 번호: 205-500-4

등급 & 순도 UPSSS grade, Single metal impurity ≤ 0.01ppb

Storage

Room temperature

Shipped In

FedEx DG Service

사양

사양 및 순도

UPSSS grade,Single metal impurity ≤ 0.01ppb

보관 조건

Room temperature

배송

FedEx DG Service

등급

우웩-레벨

이름과 식별자

정식 스마일

CCOC(=O)C

IUPAC Name

ethyl acetate

InChIKey

XEKOWRVHYACXOJ-UHFFFAOYSA-N

INCHI

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

이성체 SMILES

CCOC(=O)C

WGK 독일

1

RTECS

AH5425000

UN 번호

1173

포장 그룹

II

분자량

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
    • 분류 Carboxylic acids and derivatives
      • Subclass Carboxylic acid derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• 분류: 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
• 설명: 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

화학 및 물리적 특성

• 굴절률: 1.3720
• 발화점(°C): -3°C
• 끓는점(°C): 76.5-77.5 °C
• 녹는점(°C): -84 °C
• 분자량: 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-specific protocols (WB, IHC, IF, FC) apply to this solvent. For laboratory use, typical procedures include:

• Extraction: Mix reaction mixture with water/brine; add ethyl acetate (1–3 volumes); separate phases; repeat as needed; dry organic phase; concentrate.
• Chromatography: Choose hexane/ethyl acetate ratio by TLC scouting; pack column; elute and monitor fractions by TLC/UV/MS.

These are general literature practices and not validated test methods for this specific catalog item. For research use only.

Biological Roles

Ethyl acetate is not a biological buffer or metabolite of central biochemistry, but it has relevant interactions in biological contexts (literature, general):

• Metabolic fate: Hydrolyzed by nonspecific esterases to ethanol and acetic acid in vivo and in environmental systems; both products enter standard metabolic pathways (alcohol/acetaldehyde dehydrogenase and the TCA cycle, respectively).
• Microbial/bioprocess relevance: Commonly produced or consumed in fermentations where esterification occurs; often a component in headspace/volatilome analyses due to its characteristic odor and volatility.
• Extraction of biomolecules: Frequently used for liquid–liquid extraction of natural products, lipids, and small molecules from aqueous matrices given its intermediate polarity and limited water miscibility.
• Protein/biopolymer considerations: As an aprotic solvent, it can denature proteins at sufficient concentrations and should be excluded from aqueous enzyme assays unless intentionally employed for extraction.

No organism/target specificity is implied; this product is for research use only as noted by the manufacturer.

Buffer Applications

Not typically applicable. Ethyl acetate is an organic solvent, not a buffering agent, and is immiscible with water above ~8–9% at ambient temperature. For aqueous pH control, select conventional buffer systems (e.g., phosphate, Tris, acetate) and use ethyl acetate, if needed, only for extraction or phase-partitioning steps adjacent to buffered processes.

Green Alternatives

Ethyl acetate itself is widely regarded as a relatively green solvent (literature): low toxicity profile, readily biodegradable, derived at scale from bio-ethanol and acetic acid, and non-halogenated.

• Comparative assessment (literature, general):
  • Environmental: Low persistence, favorable EHS compared to chlorinated solvents.
  • Process: Moderate bp aids recovery by distillation; good recyclability.
  • Regulatory: Classified as an ICH Q3C Class 3 residual solvent (low toxic potential) in pharmaceuticals.

Small comparison table (literature):

• Ethyl acetate vs Dichloromethane (DCM): Non-halogenated, lower toxicity, higher bp; slightly less polar—may require longer runs or adjusted eluents in chromatography.
• Ethyl acetate vs Acetone: Both considered greener; acetone is more polar and fully water-miscible, which can complicate extractions; ethyl acetate offers better phase separation.
• Ethyl acetate vs 2-MeTHF/CPME: 2-MeTHF and CPME are also greener, less water-miscible, and more hydrophobic—often superior for moisture-sensitive chemistry; however, ethyl acetate is more benign odor-wise and typically easier to remove than CPME.

Selection guidance: Prefer ethyl acetate over chlorinated solvents for extractions and chromatography when solubility/performance allows. For highly moisture-sensitive reactions or where lower water solubility is desired, consider 2-MeTHF/CPME as alternatives.

Pharmaceutical Uses

No therapeutic or clinical claims are made. The following refers to manufacturing/formulation roles (literature/general):

• Process solvent: Widely used in API synthesis for reactions, crystallizations, and extractions due to favorable EHS profile and ease of removal.
• Purification: Common in normal-phase flash chromatography and as an anti-solvent or co-solvent for crystallization.
• Coating/formulations: Utilized as a volatile carrier in film coatings and polymer processing where rapid evaporation is desired.
• Residual solvent classification: Recognized under ICH Q3C as a Class 3 residual solvent (low toxic potential), generally permitting higher limits compared to Class 2 solvents—final product limits must comply with compendial/ICH guidance.

Item-specific pharmacopeial status, residual-solvent limits, or compliance statements: Not specified for this item; refer to CoA/Spec Sheet and applicable regulatory guidelines.

Physical Properties

Only literature/general values are provided here for professional reference; they are not item-specific specifications.

• Phase/appearance (literature): Colorless, volatile liquid with characteristic fruity odor.
• Boiling point (literature): ~77–78 °C at 1 atm.
• Melting point (literature): ~−83 to −84 °C.
• Density (literature): ~0.900–0.905 g/mL at 20 °C.
• Refractive index (literature): nD20 ≈ 1.372.
• Dielectric constant (literature): ~6.0 at 20 °C.
• Vapor pressure (literature): ~70–95 mmHg at 20 °C (varies by source/method).
• Water solubility (literature): Moderately soluble; mutual solubility ~8–9% at 20–25 °C; forms a two-phase system with water at higher proportions.
• Polarity parameters (literature): Snyder polarity index ≈ 4.4; Hansen solubility parameters δD ≈ 15.8, δP ≈ 5.3, δH ≈ 7.2 (MPa^1/2).

Item-specific specifications such as exact density, refractive index, moisture content, UV cutoff, metals, or peroxide content: Not specified for this item; refer to CoA/Spec Sheet.

Quality and Grades

• Stated grade/purity in Product Data: UPSSS grade. No additional specifications (UV cutoff, moisture, acidity, residue on evaporation, assay, stabilizers) are listed.
• Interpretation/guidance:
  • The UPSSS designation is not defined in the provided data. Item-specific acceptance limits and analytical controls are therefore: Not specified for this item; refer to CoA/Spec Sheet.
  • For demanding applications (e.g., trace analysis, LC/GC, photochemistry), consult the CoA for parameters such as nonvolatile residue, water by Karl Fischer, acidity/alkalinity, metals, and UV absorbance.
• Comparison to common solvent grades (general, literature):
  • ACS/AR grade: Meets analytical reagent limits for typical impurities.
  • HPLC grade: Low UV absorbance, filtered for particulates; suitable for chromatography.
  • Anhydrous/dry solvent: Controlled low water content, packaged under inert gas.

If your workflow requires specific limits (e.g., water ≤50 ppm, UV cutoff ≤240 nm), confirm suitability against the CoA for this exact lot of E1523836.

Reaction and Applications

This product is primarily a solvent; it also participates as a reagent under certain conditions.

• As a solvent (general, literature):
  • Frequently used for esterifications (Fischer), acylations with acid chlorides/anhydrides (as medium), oxidations (e.g., Swern workups often switch to EtOAc for extraction), and catalytic cross-couplings where a moderately polar, non-coordinating medium is desired.
  • Workup/extraction: Excellent for partitioning organic products from aqueous phases; easy removal due to moderate bp.
  • Purification: Ubiquitous in normal-phase chromatography; common TLC eluent with hexanes.
• As a reagent (general, literature):
  • Under strong basic conditions (e.g., NaOEt/EtOH), undergoes Claisen self-condensation to give ethyl acetoacetate.
  • With organometallics (RMgX, RLi), two equivalents typically add to give a tertiary alcohol after hydrolysis (ester as electrophile).
  • Acid/base-catalyzed transesterification exchanges the ethyl group with other alcohols.
• Practical tips:
  • Drying (literature): Can be dried over molecular sieves (3Å/4Å) or with anhydrous salts (e.g., CaCl2, MgSO4) for routine use. Avoid strong basic drying agents that promote hydrolysis.
  • Degassing: Nitrogen/argon sparging or sonication when oxygen-sensitive catalysts are used.
  • Removal: Rotary evaporation at ~30–40 °C bath under reduced pressure; final traces can be removed by azeotropic co-evaporation with heptane/hexane if needed.

Note: Item-specific stabilizers or inhibitors are not listed; Not specified for this item; refer to CoA/Spec Sheet.

Reaction Conditions

General literature guidance for common uses of ethyl acetate (not item-specific specs):

• Solvent in chromatography: Typical normal-phase eluent systems range from hexane:EtOAc 95:5 to 50:50 v/v for TLC/flash, adjusted to Rf/retention of target analytes.
• Liquid–liquid extraction: Partitioning with water/brine; multiple extractions with 0.5–1 volume portions often increase recovery. Dry organic layer over anhydrous MgSO4 or Na2SO4.
• Claisen condensation (self): NaOEt (1.1–1.5 equiv) in EtOH, 0 °C to reflux; slow addition of EtOAc; quench with acid then isolate β-keto ester. Reported isolated yields commonly 60–80% (literature, varies with setup/scale).
• Transesterification: Acid catalysts (p-TsOH, sulfuric) or base (NaOMe/NaOEt), 20–78 °C; remove ethanol by azeotropic distillation to drive equilibrium.
• Organometallic addition to ester: Perform in ethereal solvents or hydrocarbons; if EtOAc is substrate (not solvent), maintain low temperature initially (−78 to 0 °C) then warm; two equivalents RMgX typically required; yields dependent on substrate and workup.
• Drying/degassing: 3Å/4Å molecular sieves overnight or Karl Fischer titration-controlled drying; inert gas sparging to remove dissolved oxygen for oxygen-sensitive catalysts.

Always adapt to substrate/catalyst requirements and consult primary literature or process development data.

Safety and Handling

Follow institutional safety practices and consult the SDS for authoritative guidance. Product is shipped via FedEx DG Service, indicating dangerous goods classification for transport.

• GHS/SDS information: Not provided in Product Data. Typical classifications for ethyl acetate (literature) include:
  • Flammable liquid, Cat. 2; Eye irritation, Cat. 2A; STOT SE (narcotic effects), Cat. 3.
  • Common H-statements (literature): H225 (Highly flammable liquid and vapor), H319 (Causes serious eye irritation), H336 (May cause drowsiness or dizziness). Pictograms: GHS02, GHS07. Verify on the SDS for this lot.
• Primary hazards (general):
  • High flammability; low flash point (literature: ~−4 °C, closed cup). Vapors may form explosive mixtures with air (wide flammability range).
  • Irritation to eyes/respiratory tract; CNS effects at high vapor concentrations (literature).
• Incompatibilities (general): Strong oxidizers; strong bases and nucleophiles (hydrolysis/condensation); strong acids (catalyze hydrolysis); reactive metals if moisture/alcoholates are present.
• Handling controls:
  • Use in a fume hood; eliminate ignition sources; ground/bond containers during transfer.
  • Wear appropriate PPE: safety glasses or goggles, solvent-resistant gloves (e.g., nitrile), lab coat.
• First aid (overview; consult SDS):
  • Inhalation: Move to fresh air; monitor breathing; seek medical attention if symptoms persist.
  • Eye/skin contact: Rinse with water for at least 15 minutes; remove contaminated clothing.
  • Ingestion: Rinse mouth; do not induce vomiting; obtain medical attention.
• Waste: Collect as halogen-free organic solvent waste; follow local regulations.

Solvent Selection

Ethyl acetate is a moderately polar, aprotic, ester solvent with broad utility in synthesis, workups, and chromatography.

• Solvent profile (literature):
  • Polarity: Medium (Snyder ≈ 4.4); dielectric constant ~6.0.
  • Donor/acceptor behavior: Weak Lewis base; poor H-bond donor; modest H-bond acceptor via the carbonyl oxygen.
  • Miscibility: Miscible with many organics (alcohols, ethers, chlorinateds, aromatics). Partially miscible with water (~8–9% at 20–25 °C); forms biphasic systems at higher water content.
• When to choose ethyl acetate:
  • As an extraction solvent paired with water/brine due to favorable partitioning and low density (organic phase on top).
  • For normal-phase chromatography and TLC, commonly mixed with hexane/heptane to tune elution strength.
  • As a greener alternative to halogenated solvents (e.g., dichloromethane) when similar solvation is adequate.
• When to avoid:
  • Strongly basic or nucleophilic conditions (prone to saponification/transesterification).
  • Reactions employing powerful organometallic reagents (e.g., Grignards, alkyllithiums) that will consume the ester.

Small comparison (literature):

• Versus DCM: Less dense, higher bp (~77 °C vs ~40 °C), non-halogenated, often greener but less polar.
• Versus THF: Higher bp and lower polarity; less prone to peroxide formation; poorer solubility for salts.
• Versus Acetone: Less polar; often gives better phase separation in extractions.

Storage and Reconstitution

• Storage conditions (from Product Data): Room temperature.
• Shipping (from Product Data): FedEx DG Service (dangerous goods); handle as a flammable liquid upon receipt.
• Container/handling (general): Store tightly closed in a flammables cabinet, away from heat, sparks, and open flame. Use containers compatible with organic solvents (amber glass or approved metal) with PTFE-lined caps to minimize vapor loss.
• Stability (general literature): Chemically stable under ambient conditions; slowly hydrolyzes in the presence of strong acids/bases or moisture over long periods. Protect from prolonged exposure to strong light/UV and from reactive contaminants.
• Reconstitution: Not applicable—supplied ready-to-use as a liquid solvent. If dryness is critical for your application, condition with 3Å/4Å molecular sieves prior to use and verify by Karl Fischer as needed.
• Research use: As stated by the manufacturer—For research use only.

Any item-specific stabilizers, inhibitors, water content, or assay: Not specified for this item; refer to CoA/Spec Sheet.

Structure and Identity

Ethyl acetate (SKU: E1523836) is a simple aliphatic ester widely used as an organic solvent.

• Item-specific identifiers (from Product Data):

  • CAS: 141-78-6
  • Catalog Category: 材料科学 (Materials Science)
  • InChIKey: 415824 (as provided in Product Data)

• Literature/computed identifiers (general reference; not item-specific specs):

  • Molecular formula (literature): C4H8O2
  • Molecular weight (literature): 88.11 g/mol
  • SMILES (literature): CCOC(=O)C
  • InChIKey (literature): XEKOWRVHYACXOJ-UHFFFAOYSA-N

• Structural features (general chemistry):

  • Functional group: Carboxylic acid ester (ethyl alkoxy substituent on an acetyl group).
  • Backbone: Acetyl carbonyl (CH3–C(=O)–) linked via an oxygen to an ethyl group (–O–CH2–CH3).
  • Stereochemistry: None (achiral, no stereogenic centers).
  • 2D description: A central carbonyl C=O with the carbonyl carbon bonded to a methyl group and to an alkoxy oxygen; the alkoxy oxygen connects to a –CH2–CH3 chain.

Synthetic Utility

Beyond its role as a solvent, ethyl acetate participates in several cornerstone transformations (literature):

• Carbon–carbon bond formation:
  • Claisen condensation (self- or crossed) to yield β-keto esters (e.g., ethyl acetoacetate) using alkoxide bases (typically NaOEt in EtOH).
  • Enolate chemistry: Deprotonation α to the carbonyl (pKa ~25 in DMSO, literature) enables alkylation/acylation when used as a substrate rather than solvent.
• Nucleophilic additions:
  • Twofold addition of organometallic reagents (RMgX/RLi) to the ester carbonyl affords tertiary alcohols after aqueous workup.
• Transesterification/hydrolysis:
  • Acid- or base-catalyzed exchange with other alcohols; base-catalyzed saponification to ethanol + acetate salts.
• As a non-coordinating medium:
  • Beneficial in reactions where coordinative inhibition by ethers/amides is detrimental (certain Lewis-acid catalyzed reactions, acylations, or halogenations).

Constraints/practical notes:

• Avoid with strong bases/nucleophiles if using as solvent—risk of consumption and side-products.
• For moisture-sensitive chemistry, dry thoroughly over sieves; confirm water content by KF when critical (specs not provided for this item).

Target Specificity

Not applicable. This product is a small-molecule solvent (ethyl acetate), not a biological affinity reagent or antibody. No antigen/epitope/clone/isotype information is relevant.