Ethyl 3-ethoxy-4-methylbenzoate , CAS No.1196047-01-4

CAS: 1196047-01-4 Cat. No.: E971625 Fórmula: C₁₂H₁₆O₃ Peso molecular: 208.250

Storage

Room temperature

Specifications

Condiciones de almacenamiento de almacenamiento

Room temperature

Nombres e identificadores

• Sonrisas canónicas: CCOC1=C(C=CC(=C1)C(=O)OCC)C
• IUPAC Name: ethyl 3-ethoxy-4-methylbenzoate
• InChIKey: JEUNHRSFFDHSOX-UHFFFAOYSA-N
• INCHI: 1S/C12H16O3/c1-4-14-11-8-10(7-6-9(11)3)12(13)15-5-2/h6-8H,4-5H2,1-3H3
• Peso molecular: 208.250

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Clase Benzene and substituted derivatives
      • Subclass Benzoic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Clase: Benzene and substituted derivatives
• Subclass: Benzoic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzoic acid esters
• Alternative Parents: Phenoxy compounds Phenol ethers Benzoyl derivatives Toluenes Alkyl aryl ethers Carboxylic acid esters Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Benzoate ester - Phenoxy compound - Phenol ether - Benzoyl - Toluene - Alkyl aryl ether - Carboxylic acid ester - Ether - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Aromatic homomonocyclic compound
• Descripción: This compound belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic 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

• Peso molecular: 208.250 g/mol
• XLogP3: 2.800
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 208.11 Da
• Monoisotopic Mass: 208.11 Da
• Topological Polar Surface Area: 35.500 Ų
• Heavy Atom Count: 15
• Formal Charge: 0
• Complexity: 203.000
• 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 tested bioassay or immunoassay protocols are provided for this item. For synthetic use, follow standard organic laboratory protocols relevant to the transformations described (e.g., saponification, transesterification, halogenation). If preparing stock solutions for screening, typical practices include dissolving in DMSO or ethanol to 10–100 mM and diluting into assay media while maintaining <1–2% organic cosolvent; verify solubility and stability experimentally.

Biological Roles

This compound is a small, non-natural aromatic ester used as a synthetic intermediate. It does not have established endogenous biological roles.

• General considerations (literature/general)
  • Aromatic benzoate esters can display hydrophobic interactions with proteins and membranes but are typically used in chemistry workflows rather than biological assays.
  • Potential use contexts include serving as a precursor to phenolic, amide, or acid derivatives for probe or material synthesis.

No biological function or pathway participation is specified for this item. For any biological testing, use appropriate controls and adhere to “For research use only” guidance.

Buffer Applications

Not typically applicable. Ethyl 3-ethoxy-4-methylbenzoate is a hydrophobic organic building block, not a buffering reagent. If used in biochemical assays, it would be dissolved in an organic cosolvent (e.g., DMSO, ethanol) and diluted into the assay buffer with attention to solvent tolerances.

Green Alternatives

While this product is a target molecule/intermediate (not a solvent), greener choices can be made in its synthesis and handling.

• Greener solvent choices (literature guidance)

  • Replace chlorinated solvents (DCM, chloroform) with ethyl acetate, 2-MeTHF, CPME, or toluene when compatible. These reduce halogenated waste and can improve E-factor.
  • For ester hydrolysis or transesterification, use ethanol or methanol as both reagent and solvent; consider solvent recycling.

• Greener oxidation and deprotection

  • Benzylic oxidation: prefer O2/air with metal–organic catalysts (e.g., Co/Mn/NHPI) or electrochemical methods over stoichiometric KMnO4/Cr(VI).
  • O-Dealkylation: consider catalytic hydrogenolysis routes or oxidative demasking under peroxide-free conditions; avoid large excesses of BBr3 when possible.

• Process intensification

  • Flow chemistry for EAS or acylations can improve heat/mass transfer and safety. Micellar catalysis (aqueous surfactant media) may enable some cross-couplings after halogenation, reducing organic solvent use.

• Small comparison (illustrative; literature)

  • DCM vs EtOAc: EtOAc is biorenewable-compatible, lower toxicity; may require longer reaction times or different catalysts.
  • THF vs 2-MeTHF: 2-MeTHF is partly bio-based, higher boiling, forms fewer peroxides; may alter solubility and selectivity.

Select alternatives based on reaction compatibility, regulatory drivers, and LCA considerations.

Pharmaceutical Uses

No pharmacopeial or excipient status is provided for this item. As a hydrophobic aromatic ester, its role—where applicable—is as a synthetic intermediate in the preparation of more advanced molecules.

• Formulation notes (general)
  • If evaluated in formulation research, dissolution typically requires organic vehicles (EtOH, PEGs, polysorbates) due to low aqueous solubility (literature expectation).
  • Avoid medical or clinical application; “For research use only.”

Consult regulatory guidance if translating any derived compounds to GMP or development settings.

Physical Properties

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

• From Product Data

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular weight: Not specified for this item; refer to CoA/Spec Sheet. (Calculated literature value provided below.)

• Literature/computed properties (general guidance, not item-specific specs)

  • Molecular formula: C12H16O3 (derived from structure name)
  • Molecular weight (calculated): ~208.26 g/mol
  • Physical state: typically a colorless to pale liquid for many low-MW aromatic ethyl benzoates with ether substituents; crystalline solid is also possible depending on substitution (literature expectation).
  • Boiling point: aromatic ethyl benzoates commonly boil in the 250–290 °C range at 1 atm; specific BP for this isomer not located (literature range, not a spec).
  • Melting point: not located (literature); likely low or below ambient if liquid (not a spec).
  • Density: typical range for substituted ethyl benzoates ~1.05–1.15 g/mL at 20–25 °C (literature range, not a spec).
  • Refractive index: ethyl benzoates often nD20 ~1.50–1.56 (literature range, not a spec).
  • Solubility: expected low solubility in water; miscible with common organic solvents such as DCM, chloroform, toluene, EtOAc, THF, alcohols (literature expectations).
  • LogP: aromatic benzoate esters with ether substituents typically logP ~2.5–3.5 (literature expectation).

Always verify actual lot-specific properties by consulting the CoA/SDS before use.

Quality and Grades

• From Product Data

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

• Guidance on grades (general)

  • Research-grade organic building blocks are typically assessed by NMR/GC/HPLC purity, residual solvents, and identity (MS/IR). Low water and low peroxides are less critical than for ethers/solvents but moisture can influence reactions such as saponification or acylations.
  • For chromatographic or photochemical applications, UV-absorbing aromatics may require control of trace impurities that fluoresce or quench.
  • If “high-purity” or “≥98%” is specified on the CoA, this usually supports use in synthesis without pre-purification; nonetheless, many practitioners perform a brief column or triturations for exacting applications.

• Stabilizers/additives

  • No stabilizer information is provided for this item. If stabilizers or inhibitors are a concern for your process, review the CoA and request inhibitor-free material where applicable.

Reaction and Applications

As an electron-rich, substituted ethyl benzoate, Ethyl 3-ethoxy-4-methylbenzoate serves as a versatile intermediate in aromatic and ester chemistry.

• Representative applications (literature/general)

  • Hydrolysis (saponification) to 3-ethoxy-4-methylbenzoic acid under basic or acidic conditions; subsequent coupling (amide formation via EDC/HATU, mixed anhydride) or conversion to acid chlorides (e.g., SOCl2, oxalyl chloride).
  • Transesterification to alternate alkyl esters using acid catalysts (p-TsOH) or base-catalyzed alcoholysis; useful for late-stage ester tuning in SAR libraries.
  • Electrophilic aromatic substitution (EAS): ethoxy and methyl groups are ortho/para directors; remaining unsubstituted positions (2,5,6) can be targeted for nitration, halogenation, sulfonylation under controlled conditions (regioselectivity influenced by combined directing effects).
  • Benzylic oxidation: the para-methyl substituent can undergo oxidation (e.g., KMnO4, CAN, or Co/NHPI/O2 protocols) to the corresponding benzoic acid derivative; reaction conditions should protect the ethyl ester as needed.
  • O-dealkylation: the aryl ethoxy ether can be demasked to the phenol (3-hydroxy-4-methyl) under BBr3, AlCl3/thiols, or oxidative conditions, enabling further functionalization (e.g., etherification, carbamate formation).
  • Cross-coupling after halogenation: introduction of bromine/iodine at the activated positions allows Suzuki, Buchwald–Hartwig (after further transformation), or Sonogashira chemistry.

• Practical tips

  • Maintain anhydrous conditions for base-sensitive steps (e.g., metalations).
  • For regioselective EAS, perform stepwise halogenation/nitration at low temperature and monitor by TLC/GC–MS; directing-group interplay can shift outcomes.
  • Protect the ester during strong-acid demethylations/dealkylations to avoid transesterification or hydrolysis.

Reaction Conditions

General literature guidance for typical transformations of substituted ethyl benzoates (adjust to your substrate and scale):

• Saponification (to acid)

  • Conditions: 1–2 M NaOH or KOH in MeOH/H2O (4:1 to 9:1), 0–50 °C, 1–6 h; or reflux EtOH/H2O with catalytic base.
  • Workup: neutralize to pH ~2 with HCl, extract with EtOAc, dry, and concentrate. Typical yields: high (80–95%) for clean substrates.

• Acid-catalyzed transesterification

  • Conditions: ROH (5–20 equiv) with 1–10 mol% p-TsOH or H2SO4, Dean–Stark or continuous removal of alcohol if reversible; 50–110 °C. Yields: 70–95%.

• Reduction

  • DIBAL-H (1.1–2.0 equiv) in toluene/THF at −78 to −20 °C to aldehyde; quench carefully. LiAlH4 (1.5–3 equiv) in THF/Et2O at 0–25 °C to primary alcohol. Yields commonly 70–90%.

• Electrophilic aromatic halogenation

  • Conditions: NBS/NCS with Lewis acid or radical initiator in DCM/AcOH; Br2/FeBr3 for stronger activation. Control temperature (0–25 °C) to limit polysubstitution.

• O-Dealkylation of aryl ethoxy

  • BBr3 (1–3 equiv per O-alkyl) in DCM at −78 to 0 °C, 1–4 h; aqueous workup furnishes phenol. Protect ester when necessary.

• Benzylic oxidation (methyl → carboxyl)

  • KMnO4 in t-BuOH/H2O or acetone/H2O under reflux; or catalytic NHPI/Co(acac)2 with O2 at 80–120 °C. Monitor to avoid ester hydrolysis.

All conditions are literature-type guidance and must be optimized for this specific substrate and scale.

Safety and Handling

• From Product Data

  • GHS classification: Not specified for this item; refer to SDS.
  • Signal word: Not specified for this item; refer to SDS.
  • Hazard statements (H-codes): Not specified for this item; refer to SDS.
  • Pictograms: Not specified for this item; refer to SDS.
  • Storage conditions: Room temperature (per Product Data).

• General safety guidance for aromatic benzoate esters (literature/general; confirm with SDS)

  • Expected hazards: May cause skin/eye irritation and respiratory irritation if mist/vapor is generated. Avoid inhalation, ingestion, and prolonged skin contact.
  • PPE: use lab coat, safety glasses or splash goggles, and suitable gloves (e.g., nitrile). Employ local exhaust/hood when heating or spraying/aerosolizing.
  • Handling: keep containers tightly closed. Avoid strong oxidizers and strong bases/acids during storage. Prevent releases to the environment.
  • Incompatibilities: strong oxidizing agents; strong bases/acids may promote hydrolysis or transesterification. Avoid nitrating mixtures and reducing agents that could affect the aromatic ring or ester.
  • First aid (overview; defer to SDS): rinse eyes with water for several minutes; wash skin with soap and water; move exposed persons to fresh air; if ingested, rinse mouth—seek medical attention for any persistent symptoms.
  • Fire safety: combustible organic; use CO2, dry chemical, or foam. Heating may increase vapor and decomposition products (CO/CO2).

Refer to the product SDS for authoritative, lot-specific safety information.

Solvent Selection

This product is an aromatic ester building block rather than a solvent. However, choosing appropriate solvents is critical for its handling and reactions.

• Polarity and miscibility (literature expectations)

  • Expected to be hydrophobic and only sparingly soluble in water.
  • Good solubility in moderately polar aprotic and nonpolar organics: dichloromethane, chloroform, ethyl acetate, THF, toluene, xylene, acetone, and alcohols.

• Selection guidance by operation

  • Reaction medium: For ester hydrolysis or transesterification, alcohols (MeOH/EtOH) with base/acid are typical. For electrophilic aromatic substitutions or metalations, use dry, aprotic solvents (DCM, DCE, toluene, THF) per method.
  • Workup/extraction: Partition into hexanes/EtOAc or DCM/water systems; adjust polarity with EtOAc to tune Rf and extraction efficiency.
  • Purification: Normal-phase silica elution commonly uses hexanes/EtOAc (or heptane/EtOAc). Aromatic esters often show Rf in 0.2–0.6 with 10–30% EtOAc in hexanes; optimize empirically.

• Small comparison (literature guidance)

  • DCM vs toluene: DCM provides faster dissolution and lower bp for gentle removal; toluene supports higher-temperature reactions and better phase separation with aqueous media.
  • THF vs EtOAc: THF offers strong solvency and compatibility with bases; EtOAc is greener and easier to remove but less compatible with strong nucleophiles/bases.

Storage and Reconstitution

• From Product Data

  • Storage conditions: Room temperature.

• General guidance (small-molecule organic ester; literature/general)

  • Store tightly sealed under ambient dry conditions, away from light and sources of heat. Use inert atmosphere (nitrogen/argon) if long-term storage is planned to minimize oxidative processes and moisture ingress.
  • Keep away from strong acids/bases and oxidants. If sensitive procedures are intended, consider storing over desiccant.
  • Reconstitution/solution preparation: Dissolve in a suitable anhydrous organic solvent (e.g., DCM, EtOAc, THF, toluene, ethanol) to the desired concentration. Filter if necessary through PTFE (0.2–0.45 µm) to remove particulates.
  • Stability in solution: Aromatic esters are generally stable in neutral, anhydrous organic solvents for weeks at room temperature; avoid prolonged exposure to strong acids/bases to prevent transesterification/hydrolysis.

For lot-specific stability and storage recommendations, refer to the CoA and SDS. Product is for research use only.

Structure and Identity

Ethyl 3-ethoxy-4-methylbenzoate is an aromatic benzoate ester bearing an ethoxy group meta to the ester and a methyl group para to the ester.

• Item-specific identifiers (from Product Data)

  • CAS: 1196047-01-4
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • SKU: E971625

• Computed/structure-based information (literature/derived; not item-specific specifications)

  • Molecular formula (derived from structure name): C12H16O3
  • Molecular weight (calculated): ~208.26 g/mol (literature/computed)
  • Core structural features: benzene ring bearing three substituents: an ethyl ester (–CO2Et) at C1, an ethoxy substituent (–OCH2CH3) at C3, and a methyl group (–CH3) at C4.
  • Functional groups: aromatic ring, carboxylic acid ethyl ester, aryl ether (ethoxy), aryl methyl (benzylic C–H at the methyl carbon).
  • 2D description: a benzoate scaffold with electron-donating ethoxy and methyl groups on the ring; the ethyl ester consists of a carbonyl (C=O) bonded to an –OCH2CH3 group.

• Synonymy (general literature): ethyl 3-ethoxy-p-toluate; ethyl 3-ethoxy-4-methylbenzenecarboxylate (literature names).

Synthetic Utility

Key functional handles enable diverse downstream chemistry (literature/general):

• Ester functionality

  • Hydrolysis to carboxylic acid, followed by amide coupling (EDC/HOBt, HATU, CDI) or acid chloride formation (SOCl2, (COCl)2). Transesterification to tune lipophilicity.
  • Reduction to benzyl alcohols: ester → aldehyde (DIBAL-H, −78 °C) or alcohol (LiAlH4, NaBH4 with activation), enabling further derivatization (carbonate/ether formation).

• Aryl ether (ethoxy)

  • Demasking to phenol (BBr3, AlCl3–thiol, or oxidative) for subsequent O-alkylation, O-acylation, or Mitsunobu-type inversions (after conversion to phenoxide).
  • Directed metalation adjacent to the phenoxy substituent is feasible under strong bases (s-BuLi/TMEDA), guiding subsequent electrophile installation (requires careful optimization due to ester).

• Aromatic ring

  • Electrophilic substitutions at positions activated by the ethoxy/methyl groups (halogenation, nitration, sulfonation). Stepwise halogenation permits Pd-catalyzed cross-couplings (Suzuki, Sonogashira, Buchwald–Hartwig after suitable leaving group installation).
  • Benzylic oxidation of the para-methyl provides access to di-acid/acid–ester scaffolds; radical bromination at the benzylic position (NBS/AIBN) gives benzyl bromides for SN1/SN2 elaboration (protect the ester accordingly).

These features make the compound a versatile node in retrosynthetic planning for substituted anisole/toluate derivatives.

Target Specificity

Not applicable. This product is a small-molecule building block and is not an antibody, enzyme, or affinity reagent. No target, epitope, clone, or isotype information applies.

Preguntas frecuentes

How should this product be stored?

Store at room temperature.