Ethyl 2-(4-methylphenoxy)propanoate - ≥95% , CAS No.70044-36-9

CAS: 70044-36-9 Cat. No.: E941819 Summenformel: C₁₂H₁₆O₃ Molekulargewicht: 208.250

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Spezifikationen & Reinheit

≥95%

Storage

Room temperature

Reinheit

≥95%

Namen und Kennungen

• Kanonisches Lächeln: CCOC(=O)C(C)OC1=CC=C(C=C1)C
• IUPAC Name: ethyl 2-(4-methylphenoxy)propanoate
• InChIKey: SCRNPUHHVKDPRZ-UHFFFAOYSA-N
• INCHI: 1S/C12H16O3/c1-4-14-12(13)10(3)15-11-7-5-9(2)6-8-11/h5-8,10H,4H2,1-3H3
• Molekulargewicht: 208.250

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Klasse Benzene and substituted derivatives
      • Subclass 2-phenoxypropionic acid esters

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Klasse: Benzene and substituted derivatives
• Subclass: 2-phenoxypropionic acid esters
• Intermediate Tree Nodes: Not available
• Direct Parent: 2-phenoxypropionic acid esters
• Alternative Parents: Phenoxyacetic acid derivatives Phenoxy compounds Phenol ethers Toluenes Alkyl aryl ethers Carboxylic acid esters Monocarboxylic acids and derivatives Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: 2-phenoxypropionic acid ester - Phenoxyacetate - Phenoxy compound - Phenol ether - Alkyl aryl ether - Toluene - Carboxylic acid ester - Monocarboxylic acid or derivatives - Ether - Carboxylic acid derivative - Organic oxide - Organooxygen compound - Organic oxygen compound - Carbonyl group - Hydrocarbon derivative - Aromatic homomonocyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as 2-phenoxypropionic acid esters. These are aromatic compounds hat contain a phenol ether attached to the C2-atom of a phenylpropionic acid ester.
• 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: 208.250 g/mol
• XLogP3: 2.900
• 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: 195.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• 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 or platform-specific protocols are provided for this SKU. As a synthetic intermediate, typical procedures involve standard organic synthesis operations (weighing under dry conditions, reactions in anhydrous solvents, chromatographic purification, and NMR/LC–MS characterization).

For any specialized use (e.g., kinetic resolution, hydrolysis assays), consult pertinent literature and adapt conditions to your instrumentation and safety framework.

Biological Roles

This compound is a small organic ester used as a research chemical and synthetic intermediate. It is not a biological buffer or metabolite, and no endogenous biological role is expected.

• General notes (literature context):
  • Aryloxypropionates are structurally related to scaffolds explored in agrochemical research and as chiral auxiliaries or ligands in stereochemical studies; however, this SKU is provided strictly for laboratory research applications.
  • Hydrolysis in biological systems (if studied in vitro) would be expected to yield 2-(4-methylphenoxy)propionic acid and ethanol; kinetics depend on esterase activity and pH.

No specific cellular pathways, receptors, or biomolecular targets are assigned to this item.

Buffer Applications

Not a buffering reagent. Ethyl 2-(4-methylphenoxy)propanoate lacks acid/base pairs suitable for maintaining pH and is not typically used to formulate biochemical buffers.

For practical use in aqueous systems, choose appropriate buffer salts (e.g., phosphate, Tris, HEPES) and consult their specific application guidelines.

Green Alternatives

As a substrate rather than a solvent, greener choices concern the media and reagents used with Ethyl 2-(4-methylphenoxy)propanoate.

• Prefer greener solvents when feasible:

  • Replace DCM/CHCl3 with EtOAc, 2-MeTHF, CPME, or toluene where compatible.
  • Use ethanol or isopropanol for transesterification instead of methanol when possible.

• Catalysis and process intensification:

  • Employ solid acid catalysts (Amberlyst, sulfated zirconia) or enzyme catalysis (lipases) for ester exchange/hydrolysis to reduce corrosive acid/base use.
  • Water-mediated saponification at ambient temperature can minimize energy input and solvent consumption.

• Waste and workup:

  • Choose carbonate or bicarbonate washes over strong bases where appropriate; design crystallization-based isolations (post-hydrolysis to the acid) to avoid chromatographic silica waste.

• Comparison snapshot (general):

  • Conventional: DCM, strong mineral acids/bases, reflux.
  • Greener: EtOAc or 2-MeTHF, solid catalysts/biocatalysts, room-temperature or reduced-temperature processes.

Note: Selection must balance EHS benefits with reaction performance and product quality requirements.

Pharmaceutical Uses

No pharmacopeial status or excipient designation is provided for this SKU. It is supplied for research use only.

• General formulation context (non-clinical, laboratory):
  • As an organic ester, it may be used as a model substrate for esterase studies, stability assessments, or synthetic intermediate generation in medicinal chemistry workflows.
  • If used in pre-formulation research, ensure thorough assessment of hydrolytic stability and solubility in screening solvents; avoid extrapolating to clinical settings.

All uses should remain within laboratory research and development; no clinical or therapeutic claims are made or implied.

Physical Properties

• Item-specific (from Product Data):

  • Appearance: 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.
  • Other specifications (bp, mp, density, refractive index, UV cutoff, water, residuals): Not specified for this item; refer to CoA/Spec Sheet.

• Literature/computed (general reference values; not item specifications):

  • Overall polarity: Low to moderate lipophilicity expected for an aryl alkyl ester; poor water solubility, high solubility in common organic solvents (e.g., etheral, chlorinated, aromatic, and ester solvents).
  • Acid/base: Neutral; no ionizable groups under neutral conditions. Hydrolyzes to the corresponding acid and ethanol under strong acidic or basic conditions.
  • Volatility: Anticipated to be a low-volatility liquid or low-melting solid with a relatively high boiling point typical of aryl esters (qualitative, literature trend).
  • Refractive index/viscosity: Typically in the range associated with aryl esters; actual values depend on sample and temperature (literature trend).

• Solubility profile (qualitative, literature):

  • Water: Very low solubility expected.
  • Organic solvents: Miscible with many organic solvents such as dichloromethane, toluene, ethyl acetate, THF, acetone, and alcohols.

Quality and Grades

• Item-specific (from Product Data):

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

• How to interpret typical grades (general guidance):

  • Research or technical grade is suitable for most synthetic applications where trace impurities do not critically impact outcomes.
  • High-purity or GC/HPLC grades (when specified) indicate tighter control over volatile/UV-active impurities and may include low water and peroxides; these are advantageous for kinetic studies or sensitive catalysis.

• QC considerations for aryloxypropionate esters (general):

  • Identity confirmation by 1H/13C NMR (diagnostic signals: ethyl ester quartet/triplet, methine at C-2, para-methyl singlet, aromatic multiplets) and IR (ester C=O ~1735 cm−1, aryl-ether C–O stretches).
  • Purity by GC or HPLC; residual solvents and water content may be assessed by GC-HS and Karl Fischer, respectively.
  • Chiral composition: If enantioenriched material is required, CoA should specify ee and chiral method; otherwise material is typically racemic unless noted.

• Note: For definitive specifications of this SKU (E941819), including exact assay, residuals, and stabilizers, refer to the product’s CoA/Spec Sheet.

Reaction and Applications

Ethyl 2-(4-methylphenoxy)propanoate is a representative aryloxypropionate ester. While no manufacturer applications are specified for this SKU, the scaffold has broad utility in synthesis and method development.

• Typical transformations (general chemistry):

  • Hydrolysis to acid: Saponification (NaOH, KOH, MeOH/H2O, 0–50 °C) to give 2-(4-methylphenoxy)propionic acid; acid-catalyzed hydrolysis (HCl, H2SO4, reflux) is also possible.
  • Transesterification: Acidic (H2SO4, p-TsOH) or basic (alkoxide) catalysis to exchange the ethyl group for other alcohols, enabling preparation of methyl, isopropyl, benzyl, or chiral esters.
  • Resolution/enantioenrichment: Formation of diastereomeric salts of the acid (after hydrolysis) or use of enzymatic esterases/lipases for kinetic resolution of the secondary ester center (common for aryloxypropionates).
  • Coupling/derivatization: Conversion of the acid (after hydrolysis) to acid chlorides (SOCl2, oxalyl chloride) or mixed anhydrides for amide/ester coupling.

• Stability/compatibility:

  • The aryl–O–C(sp3) ether is robust toward many nucleophiles and moderate acids/bases but will not typically undergo SN2 cleavage. Avoid strongly reducing conditions that may affect the aryl ring or ether.

• Practical tips:

  • Maintain anhydrous conditions when transesterifying; remove generated ethanol (Dean–Stark or azeotropic removal) to drive equilibrium.
  • Monitor by GC or HPLC; the para-methyl group affords a distinctive 1H NMR singlet aiding identification.

Reaction Conditions

General laboratory conditions for common transformations (literature guidance; adjust to your system):

• Saponification to acid:

  • Typical: 1–2 M NaOH or KOH in MeOH/H2O (1:1 to 4:1), 0–40 °C, 1–6 h; monitor by TLC/GC. After completion, acidify to pH ~2 and extract with EtOAc.
  • Alternative: Aqueous Na2CO3/EtOH for milder conditions, longer times.

• Acid-catalyzed hydrolysis:

  • Aqueous HCl (3–6 M) or H2SO4 (1–2 M) with EtOH/H2O co-solvent, reflux, 2–12 h. Avoid prolonged heating to limit side reactions.

• Transesterification:

  • Acidic: Catalytic p-TsOH (1–5 mol%) in the desired alcohol (ROH), Dean–Stark or continuous removal of EtOH, 60–110 °C, 2–16 h.
  • Basic: Sodium alkoxide (5–20 mol%) in ROH or ROH/THF, 25–60 °C; exclude moisture.
  • Enzymatic: Lipase (e.g., CAL-B) in green solvents (2-MeTHF, MTBE) or neat alcohol, ambient–50 °C, hours–days.

• Reduction of ester (if converting downstream):

  • DIBAL-H (1.0–1.5 equiv) in toluene/hexanes, −78 to −40 °C to access the aldehyde; quench carefully. For full reduction to alcohol: LiAlH4 in THF/Et2O, 0–25 °C.

• Workup/monitoring:

  • Track by GC/HPLC; aryl ester UV response is strong at 210–230 nm. Use buffered aqueous workups to preserve the aryl ether integrity.

Note: Conditions are representative literature practices and should be optimized for scale, safety, and equipment.

Safety and Handling

• Item-specific (from Product Data):

  • GHS Classification: Not specified for this item; refer to SDS.
  • Signal Word: Not specified for this item; refer to SDS.
  • Hazard (H) Statements: Not specified for this item; refer to SDS.
  • Pictograms: Not specified for this item; refer to SDS.

• General safety guidance (consult SDS for authoritative information):

  • Likely hazards for aryl alkyl esters include eye/skin irritation and respiratory irritation upon inhalation of vapors/aerosols. Treat as a combustible organic liquid.
  • Personal protective equipment (PPE): Lab coat, safety glasses or splash goggles, and suitable chemical-resistant gloves (e.g., nitrile). Work in a fume hood to avoid inhalation of vapors.
  • Storage incompatibilities: Keep away from strong bases and strong acids that can catalyze ester hydrolysis; avoid strong oxidizing agents. Separate from sources of ignition.
  • Spill/cleanup: Absorb small spills with inert material (vermiculite, sand), collect in suitable waste containers. Ventilate area and eliminate ignition sources.
  • First aid overview: If on skin or in eyes, rinse cautiously with water for several minutes; remove contaminated clothing. If inhaled, move to fresh air. If swallowed, rinse mouth—do not induce vomiting; seek medical advice.
  • Stability notes: Esters can undergo hydrolysis under acidic or basic conditions and transesterification with alcohols under catalysis. Avoid prolonged exposure to moisture and high pH.

Solvent Selection

This product is a substrate/building block, not a laboratory solvent; therefore solvent selection refers to solvents used to process or react it.

• Practical solvent choices (general guidance):

  • Nonpolar/aromatic: Toluene, xylene — useful for elevated-temperature transesterifications or SN1-type solvolyses (rare here); good solubility for aryl esters.
  • Moderately polar aprotic: THF, MTBE, CPME, DCM, EtOAc — well-suited for base- or acid-catalyzed hydrolysis studies, coupling, or chromatographic handling.
  • Polar protic: Methanol, ethanol, isopropanol — for transesterification or solvolysis under acid/base catalysis.

• Miscibility profile (qualitative, literature):

  • Sparingly soluble in water; highly soluble in common organic solvents.

• Comparison note:

  • For greener processing, prefer EtOAc, 2-MeTHF, CPME, or ethanol when compatible with reaction and workup, instead of chlorinated solvents like DCM.

Storage and Reconstitution

• Item-specific (from Product Data):

  • Storage Conditions: Room temperature
  • Shipped In: Not specified for this item; refer to CoA/Spec Sheet.

• General storage guidance:

  • Keep container tightly closed in a dry, well-ventilated place. Protect from moisture and prolonged exposure to strong light or heat which can accelerate ester hydrolysis.
  • If long-term storage is anticipated, consider an inert gas headspace (nitrogen/argon) and store in amber glass to limit oxidative/light exposure.

• Reconstitution/handling:

  • Supplied neat (appearance not specified). If preparing solutions, use dry, oxygen-stable solvents (e.g., DCM, EtOAc, toluene, THF) and store solutions at 2–8 °C where feasible. Clearly label concentration and date of preparation.
  • Avoid repeated freeze–thaw of solutions; prepare aliquots for multi-use workflows.

Always refer to the product CoA and SDS for definitive storage guidance and stability information for SKU E941819.

Structure and Identity

Brief description: Ethyl 2-(4-methylphenoxy)propanoate is an aryloxypropionate ester featuring a para-methyl-substituted phenoxy group attached to the chiral C-2 of a propanoate ethyl ester.

• Item-specific (from Product Data):

  • CAS: 70044-36-9
  • InChIKey: 332499 (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.
  • Storage: Room temperature
  • Research Use: For research use only

• Literature/computed (general reference values; not item specifications):

  • Common name variants: Ethyl 2-(p-tolyl)oxypropanoate; Ethyl 2-(4-methylphenoxy)propionate
  • Expected molecular formula: C12H16O3 (literature/computed from structure)
  • Expected molecular weight: ~208.26 g/mol (literature/computed)
  • Representative (non-validated) SMILES: CCOC(=O)C(C)Oc1ccc(C)cc1 (literature)

• Structural features (general chemistry):

  • Functional groups: aromatic ether (phenoxy), aliphatic ester (ethyl propionate), para-methyl aryl substituent.
  • Stereochemistry: The C-2 (alpha) carbon of the propanoate is stereogenic; commercial material may be racemic unless specified.
  • 2D structure (verbal): A para-methyl-substituted phenyl ring is bonded via an oxygen (phenoxy) to the secondary carbon of a propanoate backbone; the carboxyl is esterified as an ethyl ester.

Synthetic Utility

Key functional elements enabling reactivity:

• Ester group (ethyl propanoate):

  • Transformations: Hydrolysis (acid/base), transesterification (acid/base/enzymatic), reduction to alcohols (e.g., DIBAL-H to aldehyde at low temperature; LiAlH4/NaBH4 variants as applicable), and conversion to acyl derivatives (acid chloride after hydrolysis).
  • Strategic use: Protecting/transport form of the acid; enables late-stage manipulation to acids/amides.

• Aryloxy linkage (p-tolyl–O–):

  • Robust to many conditions used in ester chemistry; useful as a placeholder aryl ether resistant to nucleophilic substitution. Under strongly activating conditions (e.g., demethylations or harsh Lewis acids), the ether generally remains intact compared to benzylic groups.

• Chiral center at C-2:

  • Platform for asymmetric synthesis studies: kinetic resolution by lipases/esterases or enantioselective hydrolysis/transesterification; formation of diastereomeric derivatives for chiral HPLC method development.

• Retrosynthetic value:

  • Accessible from 4-methylphenol (p-cresol) and 2-bromopropionic acid derivatives via Williamson etherification followed by esterification, or via O-alkylation of p-cresol with lactic acid derivatives.

• Analytical handles:

  • Distinctive NMR features (para-methyl singlet, ethyl ester quartet/triplet, secondary methine), and LC–MS-friendly mass (~208 Da, literature/computed) aid tracking in reaction optimization.

Target Specificity

Not applicable. This SKU is a small-molecule reagent and is not an antibody, enzyme preparation, or targeted biological. No antigen, epitope, or species reactivity information is associated with this item.