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
Punto di ebollizione (°C)
104-106°/0.05mm
Peso molecolare
236.260 g/mol
XLogP3
2.600
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
7
Exact Mass
236.105 Da
Monoisotopic Mass
236.105 Da
Topological Polar Surface Area
52.600 Ų
Heavy Atom Count
17
Formal Charge
0
Complexity
252.000
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
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Recensioni
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Application Protocols
No tested bioassay or immunoassay application protocols are specified for this SKU. As a synthetic intermediate, typical “protocols” correspond to organic reaction procedures, several of which are outlined under Reaction Conditions and Synthetic Utility.
If employing the compound in screening or in vitro experiments:
Prepare fresh stock solutions (e.g., 10–100 mM) in dry DMSO or acetonitrile.
Filter solutions (0.2 µm PTFE) if particulate forms.
Validate stability (avoid acetal/imine formation where undesired) and confirm concentration by quantitative NMR or UV–Vis if chromophore-based assays are used.
Research use only.
Biological Roles
This SKU is a synthetic organic building block intended for research and laboratory synthesis. It is not a biological buffer, nutrient, or biopolymer.
General considerations (no clinical/medical claims):
Structural features (aryl ether, aldehyde, ester) are common motifs in small-molecule libraries used for structure–activity exploration in chemical biology. The aldehyde can form reversible covalent adducts (Schiff bases) with primary amines in vitro, a property sometimes exploited in probe development and immobilization chemistry.
Hydrolysis of the ethyl ester under physiological conditions is possible for related esters, but rates depend strongly on pH, enzymes, and substitution; no item-specific biokinetic data are provided here.
The compound is hydrophobic with limited aqueous solubility; DMSO stock solutions may be used for in vitro assays if relevant to a research workflow (user-validated only).
Item-specific biological roles, targets, or activities are not specified for this product. For any biological testing, ensure appropriate controls, confirm solubility/aggregation behavior, and validate purity according to your application’s requirements. Research use only.
Buffer Applications
Not typically applicable. Ethyl 2-(2-formylphenoxy)butanoate is a neutral organic building block, not a buffering agent. It lacks defined acid/base pairs suitable for maintaining pH in aqueous systems.
Practical guidance:
If using this compound in aqueous biological assays, prepare stock solutions in miscible organic cosolvents (e.g., DMSO, acetonitrile) and dilute into an appropriate biological buffer (PBS, HEPES) only after confirming compatibility and absence of acetal/Schiff-base formation with buffer components.
Avoid prolonged exposure to primary amine-containing buffers if preserving the aldehyde functionality is critical.
Green Alternatives
While the product itself is a target building block (not typically replaced one-for-one), greener choices can be made in its use and in route design:
Solvent selection:
Prefer ethyl acetate, 2-MeTHF, CPME, or toluene over chlorinated solvents where feasible. For many nucleophilic additions and acetalizations, 2-MeTHF provides comparable outcomes to THF with better sustainability metrics.
Oxidation/reduction choices:
Use catalytic TEMPO/bleach (aqueous, buffered) for selective aldehyde oxidation rather than chromium(VI) reagents.
Choose hydrogenation or transfer hydrogenation (e.g., HCO2NH4/Pd-C) over stoichiometric metal hydrides when compatible.
Protection strategies:
Minimize protection by leveraging chemoselective reagents (e.g., NaBH(OAc)3 for reductive amination in EtOAc) to reduce steps and waste.
Workup/waste:
Replace brine-heavy liquid–liquid extractions with solid-supported scavengers where possible. Employ solvent recycling for EtOAc/2-MeTHF.
Compact comparison (general):
THF vs 2-MeTHF: Similar reactivity; 2-MeTHF has bio-based origins, higher boiling point (easier separation), and improved safety profile.
DCM vs EtOAc: EtOAc is biodegradable and non-chlorinated; may require larger volumes for solubility but reduces halogenated waste.
Note: These recommendations concern process choices around this reagent. The molecular structure itself is defined by the application need and is not typically substituted for a “greener” analog without changing project objectives.
Pharmaceutical Uses
No pharmacopeial or excipient status is specified for this item; refer to CoA/Spec Sheet.
Context (general, non-clinical):
As a multifunctional aromatic aldehyde–ester, this compound may serve as an intermediate in the synthesis of small-molecule candidates or fragrance/materials components in R&D settings. It is not offered here for therapeutic use, finished dosage forms, or GMP manufacturing.
Considerations for formulation research (if applicable to in vitro studies):
Prepare concentrated stocks in dry DMSO or EtOH; verify stability against acetal or Schiff-base formation depending on excipients.
Control residual solvents and aldehyde content according to your internal specifications if advancing intermediates.
Research use only. No medical or clinical claims are made for this product.
Physical Properties
Item-specific specifications:
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: 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/computed (general reference; not item specifications):
Empirical formula (from structure analysis): C13H16O4
Physical state: often oils or low-melting solids for analogous aryl-oxy α-substituted esters; exact MP/BP for this SKU not established here.
Solubility (typical behavior of similar compounds):
Good solubility in moderately polar organic solvents (e.g., ethyl acetate, dichloromethane, toluene, THF).
Limited solubility in water expected due to hydrophobic aromatic/alkyl content.
Partitioning: logP for comparable aryl ether–esters typically in the 2–3.5 range (literature trend; specific value for this item not established).
Spectroscopic hints:
1H NMR: characteristic aldehyde singlet ~9.7–10.2 ppm; ethyl ester quartet/triplet; α-CH adjacent to carbonyl ~3.6–4.4 ppm; aromatic multiplets ~6.8–8.0 ppm.
IR: strong C=O stretches for ester (~1730–1750 cm−1) and aldehyde (~1690–1720 cm−1), aldehyde C–H ~2720–2820 cm−1.
Any precise values (bp, mp, density, refractive index, UV cutoff, water/peroxide/metal limits) are not specified for this item; refer to CoA/Spec Sheet.
Quality and Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
Guidance for interpreting potential grades (general information for planning only):
Research grade: Suitable for most synthetic applications. If using in sensitive catalysis, consider additional purification (e.g., bulb-to-bulb distillation under reduced pressure, silica filtration) to remove trace acids or peroxides (if any formed during storage in alcohol-containing media).
HPLC/GC grade solvents are formulated for low UV/background; this reagent is a building block rather than a solvent—UV cutoffs are typically irrelevant, but trace carbonyl impurities may influence photochemical steps or polymerizations.
Metal content and trace moisture: For base- or metal-catalyzed reactions (e.g., enolate chemistry, Wittig, Pd coupling after further derivatization), low water and metal background is beneficial. If such limits matter to your workflow, request CoA with Karl Fischer and metal screening or pre-dry/polish in-lab.
What is specific to this SKU:
Storage is designated at room temperature (per Product Data). No further item-specific quality constraints are provided here; consult the CoA/SDS shipped with your lot for exact assay, impurity profile, and any stabilizer package.
Reaction and Applications
Ethyl 2-(2-formylphenoxy)butanoate is a multifunctional synthon enabling orthogonal transformations at the aldehyde, ester, and ether linkages.
Reductive amination with primary amines to give benzylated secondary amines (NaBH3CN, NaBH(OAc)3).
Wittig/Horner–Wadsworth–Emmons olefinations to introduce styrenyl or vinyl ether motifs ortho to oxygen.
Nucleophilic additions (RMgX, R2CuLi, RZnX) delivering secondary/tertiary benzylic alcohols; protect ester or control equivalents to avoid ester reaction.
Oxidation to the corresponding salicylate-type acid (selective aldehyde oxidation conditions such as TEMPO/bleach).
Aldehyde protection: Formation of acetals/hemiacetals with diols (e.g., ethylene glycol, 1,3-propanediol) to mask aldehyde during base-intensive steps.
Ester handle:
Hydrolysis to 2-(2-formylphenoxy)butanoic acid (acid/base conditions; control to avoid aldehyde hydration/overreaction).
Reduction (LiAlH4/DIBAL-H) to corresponding diol/allylic alcohol motifs; chemoselectivity must be managed relative to the aldehyde (often protect as acetal/oxime first).
Enolate generation at the α-position for alkylation or aldol-type couplings; the adjacent aryl-oxy group may influence acidity and stereocontrol.
Intramolecular cyclizations:
o-Formyl phenoxy systems are precursors to benzofuran frameworks via aldol-type or dehydrative cyclizations after appropriate side-chain activation.
Use cases:
Assembly of benzofuran/benzopyran libraries, fragrance intermediates, and advanced intermediates in materials/medchem campaigns (research use only). The orthogonal reactivity allows convergent route design and late-stage diversification.
Reaction Conditions
General literature conditions for typical transformations of aromatic aldehyde–esters (select examples; user optimization required):
Reductive amination of the aldehyde:
Solvent: MeOH, EtOH, or EtOAc; keep water low.
Reagents: NaBH3CN (pH 6–7 acetate buffer) or NaBH(OAc)3 (neat AcOH/CH2Cl2 or EtOAc).
Temp: 0–25 °C; Time: 2–18 h. Typical yields for analogous systems: 60–90%.
Wittig olefination:
Solvent: THF or toluene; ylide from Ph3P=CHR.
Temp: −78 to 25 °C depending on ylide stability; Time: 1–16 h. E/Z outcomes depend on ylide.
Nucleophilic addition (Grignard/organolithium) to aldehyde:
Solvent: anhydrous THF/Et2O/2-MeTHF.
Temp: −78 to 0 °C initially, then warm to RT; Time: 0.5–4 h.
Protect or tolerate the ester as needed; use milder organozincs to improve chemoselectivity.
Aldehyde oxidation to acid:
TEMPO (0.05–0.1 equiv), NaOCl (pH ~9, buffered), solvent: biphasic CH2Cl2/H2O or AcOEt/H2O, 0–25 °C, 1–3 h; selective for aldehyde over ester.
Ester hydrolysis:
Basic: NaOH/MeOH–H2O, 0–25 °C; Acidic: HCl/MeOH reflux. Protect aldehyde (acetal) to avoid side reactions.
Ester reduction:
DIBAL-H (1.1–1.5 equiv) in toluene/CH2Cl2 at −78 to −40 °C to halt at aldehyde stage after protection of the aryl aldehyde; LiAlH4 for full reduction to alcohol.
α-Enolate formation and alkylation:
Base: LDA or LiHMDS in THF; −78 to −20 °C; electrophiles: alkyl halides, aldehydes (aldol). Quench with careful workup to preserve aldehyde if unprotected.
These conditions are general literature guidance for similar scaffolds and are not item specifications. Verify on small scale and adapt to your substrate and equipment.
Safety and Handling
Item-specific hazard data:
Signal word: Not specified for this item; refer to SDS.
H-statements / GHS classification / Pictograms: Not specified for this item; refer to SDS.
General safety considerations for aromatic aldehyde–esters (literature/good practice):
Hazards: May cause skin/eye irritation; aldehydes can be sensitizers and are reactive toward nucleophiles. Avoid inhalation of vapors and contact.
PPE: Use lab coat, nitrile gloves, safety glasses/goggles. For scale-up or aerosol generation, consider splash goggles and face shield.
Engineering controls: Work in a fume hood. Provide local exhaust during transfers and reactions that heat or generate vapors.
Incompatibilities: Strong oxidizers (risk of rapid oxidation of aldehyde); strong bases/acids (can promote hydrolysis/transesterification); strong nucleophiles (Schiff base/acetals). Avoid prolonged exposure to moisture if aldehyde integrity is critical.
Stability notes: Aldehyde functions can oxidize to acids and form acetals/hemiacetals with alcohols; minimize air/light exposure for long-term storage. No known peroxide formation tendency (unlike dialkyl ethers), but general periodic testing is prudent only if stored for extended periods under air.
First aid (overview; consult SDS):
Skin/eye: Rinse with water for at least 15 minutes; remove contaminated clothing; seek medical attention if irritation persists.
Inhalation: Move to fresh air; seek medical attention if symptoms occur.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Spill/Fire: Absorb small spills with inert material; for fire use CO2, dry chemical, or foam. Combustible organic liquid/solid—avoid ignition sources.
Always consult the product SDS for authoritative safety information.
Solvent Selection
This product is a substrate/building block rather than a process solvent. Nevertheless, solvent choice affects reactivity and handling.
General solubility/miscibility expectations (literature trends):
Good solubility in ethyl acetate, dichloromethane (DCM), chloroform, toluene, THF, acetone, and acetonitrile.
Limited solubility in alcohols if acetalization is not desired; alcohols can react with aldehydes under acid catalysis.
Poor solubility in water expected.
Selection by transformation:
Acetal formation/protection: Use dry alcohol (MeOH, EtOH) with catalytic acid (e.g., p-TsOH) if desired; otherwise avoid protic solvents to preserve aldehyde.
Nucleophilic additions to aldehyde (e.g., Grignard, organozinc via transmetallation): Use aprotic, anhydrous solvents (THF, 2-MeTHF, toluene). Protect ester as needed if base-sensitive conditions are used.
Enolate chemistry at the ester α-position: Polar aprotic solvents (THF, DME) with strong bases (LDA, LiHMDS) at low temperature.
Oxidation of aldehyde to acid: Aqueous-organic biphasic systems (e.g., AcOEt/H2O) with NaClO2 or TEMPO/NaOCl are common; ester stability must be considered (selective aldehyde oxidation possible with TEMPO variants).
Comparisons:
THF vs 2-MeTHF: 2-MeTHF offers greener profile and similar reactivity for many nucleophilic additions.
DCM vs EtOAc: EtOAc is less hazardous and often dissolves aryl esters adequately; choose EtOAc when chlorinated solvents are to be avoided.
Always dry and degas solvents when moisture or oxygen sensitivity of the planned step requires it.
Storage and Reconstitution
Item-specific storage:
Storage Conditions: Room temperature (per Product Data).
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
Good-practice handling for aldehyde–esters (general):
Store tightly closed in an amber glass bottle to limit light exposure and potential aldehyde oxidation. If long-term storage is anticipated, consider inert gas blanket (N2/Ar) and a desiccated cabinet.
Avoid prolonged contact with acidic/basic vapors or alcohol-rich atmospheres to minimize acetalization or transesterification.
Do not freeze unless stability has been verified; some oils/low-melting solids can crystallize heterogeneously and trap impurities.
Reconstitution/Preparation:
If solidified, warm gently to ambient and swirl to homogenize. If needed for solution use, prepare concentrates in dry, aprotic solvents (e.g., DCM, EtOAc, THF, toluene) or DMSO for assay work; confirm compatibility before use.
For moisture-sensitive transformations, pre-dry over molecular sieves (3Å/4Å) or pass through a short plug of basic alumina/silica to remove trace acids formed during storage.
Shelf-life considerations:
Monitor by 1H NMR (aldehyde proton ~9.7–10.2 ppm) or HPLC for signs of oxidation to acid or acetal formation. Refer to CoA for any lot-specific stability guidance.
Research use only.
Structure and Identity
Ethyl 2-(2-formylphenoxy)butanoate is an aromatic ether–aldehyde–ester tri-functional building block, combining an o-formylphenoxy unit with an α-substituted ethyl butanoate.
Item-specific identifiers (from Product Data):
CAS: 86602-60-0
CID (PubChem): 2764072
InChIKey: 314884 (as provided)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Computed/literature structural information (non-spec, for reference):
One stereogenic α-carbon (at C-2 of the butanoate) unless specified otherwise; product data do not define configuration (racemic likely unless stated).
2D structure description:
An ethyl butanoate chain bearing at C-2 an O-aryl substituent; the aryl is a phenyl ring carrying an ortho-formyl (–CHO) relative to the phenoxy oxygen.
Notes:
Only the identifiers listed under item-specific are guaranteed for this SKU. All other representations are general/literature descriptions provided to aid planning and are not item specifications.
Synthetic Utility
Key reactive sites and their value in synthesis:
o-Aryl aldehyde:
Gateway to benzylic alcohols (hydride or organometallic addition), olefins (Wittig/HWE), imines/oximes (Schiff-base chemistry), and acids (chemoselective oxidation). The ortho relationship to oxygen can enable directed metalation or cyclizations to benzofurans/benzopyrans after further manipulation.
Ethyl ester:
Convertible handle: hydrolysis to acid, alcoholysis to alternate esters, reduction to primary alcohols (via DIBAL-H or LiAlH4 with protection of aldehyde), and enolate generation for α-functionalization. The α-stereocenter can be set using chiral auxiliaries or organocatalysis in alkylation/aldol steps.
Phenoxy ether linkage:
Stabilizes the aryl-alkyl connection; can act as a leaving group precursor after activation (e.g., demethylation-type approaches don’t directly apply; however, directed ortho metalation adjacent to oxygen is sometimes facilitated by the phenoxy group enabling further ring functionalization).
Retrosynthetic value:
Disconnection at the ether suggests coupling of 2-formylphenol with an α-halo or sulfonate of ethyl 2-hydroxybutanoate derivative (or Mitsunobu-type etherification), or acylation-first then O-alkylation strategies.
Aldehyde introduction can arise from formylation (e.g., Reimer–Tiemann/Vilsmeier on a protected phenol precursor) followed by etherification and ester installation.
This orthogonal triad of functionalities supports modular route design with late-stage selectivity options.
Target Specificity
Not applicable. This product is a small-molecule reagent/building block and is not an antibody, enzyme, or probe with defined biological target specificity. No antigen/epitope/isotype or species reactivity data are relevant.
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