This compound belongs to the class of organic compounds known as phenoxyacetic acid derivatives. These are compounds containing an anisole where the methane group is linked to an acetic acid or a derivative.
External Descriptors
Not available
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.
Certificati (CoA, COO, BSE/TSE e tabella di analisi)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Proprietà chimiche e fisiche
Peso molecolare
252.260 g/mol
XLogP3
2.000
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
8
Exact Mass
252.1 Da
Monoisotopic Mass
252.1 Da
Topological Polar Surface Area
61.800 Ų
Heavy Atom Count
18
Formal Charge
0
Complexity
266.000
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
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Recensioni
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Application Protocols
No manufacturer-validated biological or analytical protocols are provided for this item. Typical laboratory protocols would follow standard organic synthesis procedures relevant to aldehydes and esters (e.g., imine formation, Wittig olefination, ester hydrolysis/coupling) as outlined in the Reaction Conditions section.
For any new application, perform reaction optimization on millimole scale first, establish analytical tracking (TLC, LC–MS, NMR), and document impurity profiles prior to scale-up.
Biological Roles
This product is a synthetic aromatic aldehyde–ester and does not have an established natural biological role or recognized participation in endogenous metabolic pathways.
General context (non-clinical, for research only):
Aromatic aldehydes can serve as precursors to ligands, probes, or polymer modifiers via imine/oxime linkages to biomolecules in chemical biology workflows. Any such use is exploratory and demands thorough purification and characterization.
The ester moiety can be transformed to the corresponding acid or amide to modify physicochemical properties (e.g., lipophilicity, charge) of target molecules in SAR campaigns.
Cautions:
No data are provided for bioactivity, toxicity thresholds, or ADME properties for this specific compound. Do not infer pharmacology from functional groups alone.
Use exclusively in controlled laboratory experiments; not intended for any diagnostic, therapeutic, or food/cosmetic application.
If biological testing is contemplated, establish dedicated analytical methods (LC–MS, NMR) to confirm identity/purity before exposure to cells or enzymes, and consult institutional biosafety guidelines.
Buffer Applications
Not typically applicable. Ethyl 2-(2-ethoxy-4-formylphenoxy)acetate is a neutral organic building block and is not used as a buffering agent or buffer component.
Practical note: If reactions are conducted in aqueous media (e.g., imine formations with water-compatible amines), choose a buffer system appropriate to the reaction (e.g., phosphate, acetate) but avoid conditions that promote ester hydrolysis or aldehyde oxidation. Keep pH near neutral and minimize residence time in water.
Green Alternatives
As a building block (not a solvent), “greener alternatives” concern solvent choice and process conditions used with this reagent rather than replacing the molecule itself.
Greener solvent options for common operations (general guidance):
Workup/extraction: Prefer EtOAc or MTBE over chlorinated solvents when phase behavior and yield allow.
Reactions: 2-MeTHF can substitute for THF in many base-mediated or organometallic steps; MeCN or EtOAc can replace DCM in some condensations/olefinations; toluene or anisole for high-temperature steps in place of xylene/chlorinated solvents.
Chromatography: Heptane/EtOAc systems reduce halogenated solvent use; use gradient scouting to minimize solvent volume.
Protection strategies to minimize waste:
Temporarily protect the aldehyde as an acetal or oxime to enable one-pot sequences (e.g., hydrolysis→coupling→deprotection) reducing isolation steps and solvent consumption.
Energy and safety:
Favor room-temperature or microwave-assisted conditions to shorten cycle times.
Avoid stoichiometric chromium or hypervalent iodine oxidants; use catalytic TEMPO/O2 or electrochemical oxidation where applicable.
DCM vs EtOAc: EtOAc is biodegradable, lower toxicity; DCM offers higher solubility but higher environmental/health burden.
THF vs 2-MeTHF: 2-MeTHF derived from biomass, higher boiling point, often better phase separation; watch for peroxide management in both (store stabilized and test periodically).
Pharmaceutical Uses
No pharmacopeial status or excipient role is specified for this item. It is supplied for research use only as a synthetic intermediate/building block.
The aldehyde group enables late-stage derivatization (e.g., imine/oxime conjugations) in discovery chemistry; the ester can be hydrolyzed to the acid for amide coupling to generate lead-like analogs.
If used in process development studies, maintain controls preventing carryover of residual aldehyde into downstream materials due to potential reactivity and odor.
Regulatory note: Absent explicit GMP documentation and pharmacopeial monograph, this material should not be used in drug product manufacturing. For any work approaching regulated contexts, specify required grades, impurity profiles, and residual solvent limits via a project-specific quality agreement.
Physical Properties
Item-specific physical data: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general expectations for this structural class (non-spec):
Phase/appearance: Typically a colorless to pale yellow liquid or low-melting solid for aryl ethers bearing aldehyde and ester groups of this size; tendency to form viscous oils.
Density/refractive index: Not widely tabulated for this exact compound; similar aryl ether esters often show ρ ~1.10–1.20 g/mL and nD ~1.52–1.56 at 20–25 °C (literature class range; not item-specific).
Boiling/melting behavior: Aldehyde–ester aromatics may decompose/oxidize upon prolonged heating; many isolate and handle them at ambient temperature without distillation. If purification is required, reduced-pressure techniques and short-path methods are preferred (general practice).
Solubility: Expected to be sparingly soluble in water and readily soluble in common organic media (EtOAc, DCM, chloroform, toluene, THF, acetone, alcohols). The polar ester and aldehyde increase solubility in moderately polar organic solvents (general behavior).
pKa/logP: No pKa (non-ionizable under neutral conditions). Aryl-ether esters with C13 framework commonly exhibit moderate hydrophobicity (literature class logP often ~2–3), but no item-specific logP is available.
Notes: Because aldehydes can hydrate or oxidize, measured properties (e.g., RI, NMR) should be collected on freshly purified material under inert atmosphere when high precision is needed.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Interpreting typical grades (general guidance for aromatic building blocks):
Synthetic/Research grade commonly targets organic purity suitable for multistep synthesis (e.g., ≥95% by HPLC/GC/NMR), with residual solvent/water/metals controlled to fit standard lab practice. Without an explicit grade label, assume research-use only material optimized for chemical synthesis, not analytical reference or GMP purposes.
HPLC grade/low UV-absorbing solvents are not applicable here; this is a solid/liquid reagent, not a solvent. For chromatographic use as a standard, seek a designated analytical reference standard grade.
Stabilizers/inhibitors: None are specified for this item. Aldehydes are sometimes supplied under inert gas or with minimal headspace. If the CoA indicates stabilization (e.g., argon blanket), maintain those conditions to preserve assay and color.
What to check on receipt (best practice):
Identity: 1H/13C NMR and HRMS consistent with C13H16O5; aldehydic proton typically appears ~9.7–10.1 ppm (literature expectation).
Purity: HPLC/GC and NMR integration; monitor for carboxylic acid byproduct (oxidation) and hydrolysis products (alcohol/acid).
Water/peroxide/metals: Not specified for this item; refer to CoA/Spec Sheet.
Reaction and Applications
Ethyl 2-(2-ethoxy-4-formylphenoxy)acetate offers two orthogonal handles enabling divergent synthesis from a single substrate.
Aldehyde-centric transformations:
Wittig/HWE/Julia–Kocienski olefinations to install styrenyl or cinnamate frameworks para to the phenoxy linker; choose base and ylide for E/Z control.
Reductions: NaBH4/CeCl3 (Luche) to benzylic alcohol; selective DIBAL-H or BH3·THF reductions can be tuned to protect the ester.
Condensations: Knoevenagel with active methylenes; Schiff base formation with amines; Oxime/hydrazone derivatives as protecting/analytical handles.
Oxidations: Mild oxidants (e.g., Ag2O, TEMPO systems) to the corresponding benzoic acid, mindful of ester integrity.
Ester/side-chain manipulations:
Saponification to the free acid, enabling amide coupling (EDC/HATU/DIC) under aldehyde-compatible conditions (low base, low temperature, short times, or temporary aldehyde protection as acetal/oxime).
Transesterification to tune solubility or enable polymer-anchoring (e.g., benzyl, t-Bu as removable handles).
Benzylic functionalization adjacent to oxygen (O–CH2–COOEt) via halogenation (NBS) or alkylation after deprotonation in specialized sequences (with caution to avoid overreaction at the aldehyde).
Aromatic framework use:
The 2-ethoxy group is an electron-donating, ortho/para-directing substituent; combined with the phenoxy and aldehyde pattern, it can steer subsequent electrophilic aromatic substitution (though the ring is already 1,2,4-trisubstituted, limiting free positions).
Applications span synthesis of fragrance intermediates, advanced pharmaceutical-like scaffolds, and materials monomers where a para-formyl directs further elaboration (research context; non-clinical).
Reaction Conditions
General literature guidance for transforming functional groups within Ethyl 2-(2-ethoxy-4-formylphenoxy)acetate (non-item-specific):
Imine/oxime formation:
Solvent: DCM, MeOH, toluene, or MeCN; molecular sieves (3Å/4Å) to remove water.
Conditions: RT to 50 °C; catalytic acid (AcOH, pTsOH) as needed. Typical times 1–12 h; monitor by TLC/LC–MS.
Reductive amination:
Solvent: DCM/MeOH or MeCN; reductant: NaBH3CN or NaBH(OAc)3.
Conditions: pH-controlled (AcOH buffer in MeOH), 0–25 °C; 2–16 h. Protect ester from base; avoid excess heat.
Aldehyde reduction (to alcohol):
Luche (NaBH4, CeCl3·7H2O) in MeOH/EtOH at 0–25 °C; minutes to 1 h.
DIBAL-H in toluene/CH2Cl2 at −78 to 0 °C for chemoselectivity.
Olefination (Wittig/HWE):
Solvent: THF, toluene, or DCM; base: n-BuLi/NaHMDS (Wittig) or mild base (HWE).
Temperature: −78 to RT; 1–6 h; E/Z control via ylide/reagent choice.
Ester hydrolysis and coupling:
Saponification: Aqueous NaOH/THF–MeOH, 0–25 °C; monitor to minimize aldehyde side reactions (or protect as acetal/oxime).
Coupling: EDC/HOBt or HATU/DIPEA in DMF/MeCN, 0–25 °C; 0.5–4 h; exclude water.
Oxidation of aldehyde to acid:
Reagents: TEMPO/NaOCl (pH ~9), Pinnick (NaClO2, NaH2PO4, 2-methyl-2-butene) in t-BuOH/H2O.
Conditions: 0–25 °C; 0.5–3 h; monitor to avoid ester cleavage.
Yields vary with substrate and conditions; consult primary literature and run small-scale scouts before scale-up.
Safety and Handling
Item-specific GHS and hazard statements: Not specified for this item; refer to the product SDS for authoritative safety classification, pictograms, and statements.
General hazards for aldehyde/aryl-ether esters (literature/experience-based):
Irritation/sensitization: Aldehydes can be skin/eye/respiratory irritants; avoid inhalation of vapors and contact.
Reactivity: Susceptible to oxidation (formyl → carboxylic acid), and to acetal/imine formation with nucleophiles. The ester can hydrolyze under strong acidic or basic conditions.
Combustibility: Organic liquid/low-melting solid; keep away from ignition sources.
PPE and engineering controls (good laboratory practice):
PPE: Safety glasses or splash goggles, lab coat, nitrile gloves (change regularly). Use additional protection when scaling up or spraying/aerosolizing.
Ventilation: Handle in a fume hood to control vapor and reaction off-gassing.
Incompatibilities (general):
Strong oxidizers (risk of exothermic oxidation of aldehyde/aryl moiety).
Strong bases/acids (ester cleavage; base-catalyzed aldol-type side reactions at the aldehyde).
Reactive nucleophiles (amines, hydrazines) form imines/oximes/hydrazones.
First-aid overview (refer to SDS for details):
Skin/eye contact: Rinse with water for ≥15 min; remove contaminated clothing; seek medical advice if irritation persists.
Inhalation: Move to fresh air; monitor breathing; seek medical attention if symptoms occur.
Ingestion: Rinse mouth; do not induce vomiting; obtain medical attention.
Waste handling: Collect aldehyde-containing organic waste separately; avoid mixing with strong oxidants. Follow institutional and local regulations.
Solvent Selection
This product is a functionalized aromatic building block rather than a solvent. Solvent discussions therefore focus on dissolving it for synthesis, purification, and analysis.
Polarity and miscibility (general behavior for aryl aldehyde–esters):
Solubility: Good in moderately polar organics such as DCM, chloroform, EtOAc, acetone, THF, MeCN, toluene, and alcohols; poor in water.
Polarity class: Moderately polar, neutral organic compound; dissolves well in solvents with donor/acceptor capability.
Selection by application:
Nucleophilic additions/condensations at the aldehyde: Use aprotic media (DCM, THF, toluene) for imine/Wittig/Knoevenagel; dry solvents minimize side reactions.
Ester transformations (hydrolysis, amidation): Alcoholic solvents for acid-catalyzed exchange; polar aprotic (DMF/DMSO/MeCN) for aminolysis or coupling; keep temperature controlled to preserve the aldehyde.
Chromatography: Normal-phase silica with hexanes/EtOAc or DCM/EtOAc gradients typically gives clean separation from polar byproducts (acids/oximes).
THF/2-MeTHF: good for base-mediated reactions; ensure dry conditions.
EtOAc: greener profile; suitable for workups and crystallizations.
MeOH/EtOH: enable acetal/imine equilibria; may promote transesterification under acid/base.
Note: Avoid strongly basic alcoholic media at elevated temperature to prevent ester cleavage and aldol-type side reactions.
Storage and Reconstitution
Item-specific storage: Room temperature (per Product Data). Store tightly closed in the original container.
Practical stability guidance (general for aldehydes/aryl esters):
Atmosphere: Prefer storage under inert gas (N2/Ar) to limit oxidation of the aldehyde to the corresponding acid.
Light/moisture: Protect from light and humidity; use amber glass and desiccation to minimize color change and hydrolysis.
Opening/use: Minimize headspace and exposure time; if long-term storage is planned, consider aliquoting.
Reconstitution/handling:
If solidified, gently warm to ambient or slightly above (≤35 °C) to liquefy; avoid prolonged heating.
For solution handling, prepare stock solutions in dry DCM, THF, toluene, MeCN, or EtOAc as needed; use freshly or store short-term at 2–8 °C under inert gas. Monitor for degradation by TLC/LC–MS prior to use.
Shipping: Not specified for this item; refer to CoA/Spec Sheet.
Research Use Only: As stated by the manufacturer, this product is for research use only.
Structure and Identity
Ethyl 2-(2-ethoxy-4-formylphenoxy)acetate is an aromatic ether bearing both an aldehyde handle and an ethyl glycolate (phenoxyacetate) ester, providing orthogonal reactivity on the same ring.
Item-specific identifiers (from Product Data):
CAS: 51264-71-2
PubChem CID: 880082
InChIKey (as provided): 445493 (truncated/short form as listed; full InChIKey not specified for this item)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Computed/literature identity (non-spec, for reference):
Molecular formula (literature/structure-derived): C13H16O5
Structural features (general chemistry description):
Aromatic core: 1,2,4-trisubstituted benzene.
Substituents:
Ortho to the phenoxy linkage: ethoxy group (–OCH2CH3), an electron-donating substituent via resonance/induction.
Para to the phenoxy linkage: aldehyde (–CHO), a strongly electrophilic formyl handle.
Through-ring oxygen: phenoxyacetic ethyl ester (–O–CH2–C(=O)–O–CH2CH3) providing a benzylic methylene adjacent to an ester (useful for O-alkyl–O cleavage strategies and side-chain elaboration).
Functional groups present: aryl ether, aliphatic ether, aldehyde, ester.
Stereochemistry: None (achiral as named; no stereocenters).
2D description in words:
A benzene ring bearing three substituents: (1) a phenoxy–CH2–COOEt chain via an oxygen at the ipso carbon, (2) an ethoxy group at the ortho position, and (3) a formyl group at the para position. The molecule thus combines an electrophilic formyl on the ring with a latent carboxyl unit (ester) on the benzylic side chain.
Synthetic Utility
Key functional groups and their uses:
Aldehyde (para to phenoxy):
Electrophile for Wittig/HWE olefination to access aryl alkenes and cinnamate motifs.
Reductive amination after imine formation to introduce benzylic amines (careful to preserve the ester; use NaBH3CN or NaBH(OAc)3 in aprotic solvents).
Oxime/hydrazone formation as a reversible protection or for conjugation handles.
Selective reduction (e.g., Luche) to benzylic alcohol without reducing the ester.
Ethyl phenoxyacetate side chain:
Saponification → acid → amide coupling (EDC/HATU) to connect to amines/peptides, typically under mild conditions with transient aldehyde protection (acetal/oxime) if needed.
Transesterification to alter protecting group strategy or solubility.
Benzylic modifications at the O–CH2– moiety (e.g., halogenation with NBS) for further diversification.
Aryl ether and 2-ethoxy substituent:
The ether donors increase ring electron density, facilitating electrophilic substitutions at remaining positions if accessible; however, the 1,2,4-trisubstitution limits open sites.
Retrosynthetic value: The molecule can converge from a para-formyl phenol via O-alkylation with ethyl bromoacetate (or 2-step via chloroacetate) and independent installation of the ortho-ethoxy substituent (e.g., via ethoxylation/alkylation), or from directed formylation (e.g., Vilsmeier–Haack) on a pre-assembled di-ether phenoxyacetate.
Target Specificity
Not applicable. This product is a small-molecule chemical reagent and is not an antibody, enzyme, or affinity reagent with defined biological target specificity.
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