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
196.200 g/mol
XLogP3
1.300
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
5
Exact Mass
196.074 Da
Monoisotopic Mass
196.074 Da
Topological Polar Surface Area
55.800 Ų
Heavy Atom Count
14
Formal Charge
0
Complexity
173.000
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
Calcolatori di soluzioni
Molarity Calculator
Determine the necessary mass, volume, or concentration for preparing a solution.
Dilution Calculator
Determine the dilution needed to prepare a stock solution.
Reconstitution Calculator
Recensioni
Recensioni dei clienti
Application Protocols
No tested bioassay or analytical application protocols are specified for this catalog item. It is supplied as a research chemical intermediate.
For synthetic use, refer to the Reaction Conditions and Synthetic Utility sections for general guidance on saponification, etherification, acylation, and reductions applicable to this scaffold. For analytical characterization in your lab, standard methods include 1H/13C NMR, IR (phenolic and ester C=O stretches), LC–MS/HRMS, and HPLC purity assessment. Lot-specific details should be obtained from the CoA/Spec Sheet.
Biological Roles
No inherent biological role is assigned to Ethyl 2-(4-hydroxyphenoxy)acetate; it is a synthetic small-molecule building block intended for research and laboratory use only.
General context (biochemistry and chemical biology, literature-based):
Phenolic ether motifs are common in natural products and biopolymers (e.g., lignin features aryl–O–alkyl linkages). The presence of a free phenolic OH provides a handle for conjugation to biomolecules via carbamates, carbonates, or ether linkages.
The aryloxyacetic acid motif (upon hydrolysis of the ethyl ester) appears in various bioactive scaffolds in agrochemical and medicinal chemistry; however, this catalog item is not supplied for biological administration and no biological activity is claimed.
Physicochemical profile: A balance of hydrogen bonding (one donor, multiple acceptors) and moderate lipophilicity typically facilitates membrane permeability of derivatives, which can be tuned by converting the ester to acids, amides, or more lipophilic esters during probe design.
Use considerations for biochemical workflows:
For bioconjugation or probe synthesis, the ethyl ester can be selectively hydrolyzed to yield the acid, enabling amide coupling to amines (peptides, linkers). The free phenolic OH can be derivatized orthogonally, allowing dual-point attachment strategies.
Research Use Note (from product data): For research use only.
Buffer Applications
This compound is not a conventional buffering agent. It lacks a conjugate acid/base pair in the physiological pH window suitable for maintaining stable pH, and it is typically used as a synthetic intermediate rather than as a buffer component.
Practical note: If included in biochemical assays, buffer choice should be driven by the chemistry being performed on the phenolic OH or carboxylate (post-hydrolysis). Use standard buffers (e.g., phosphate, HEPES, Tris) and verify compound solubility and stability in the chosen system. No item-specific buffer recipes are applicable.
Green Alternatives
Because Ethyl 2-(4-hydroxyphenoxy)acetate is a building block rather than a solvent or reagent used in large excess, “green” considerations focus on solvent choice and protecting-group strategy during its use and on greener syntheses of the scaffold.
Greener choices during use (general guidance):
Solvents: Prefer EtOAc, 2-MeTHF, CPME, or MeOH/EtOH where compatible in place of chlorinated solvents (DCM/CHCl3) or DMF. For base-promoted O-alkylation, MeCN or 2-MeTHF with K2CO3 can replace DMF/acetone in many cases.
Couplings: Use carbodiimide-free amide formations (e.g., CDI or catalytic coupling with recyclable reagents) when possible to reduce urea waste; water-soluble EDC with in situ extraction reduces organic waste.
Protection strategy: Choose easily cleavable, low-toxicity protecting groups (acetyl, carbonate) and catalytic deprotection conditions (transfer hydrogenolysis or biocatalytic deacylation) to minimize harsh reagents.
Comparative snapshot (illustrative; not product specs):
DCM vs EtOAc: EtOAc offers lower toxicity and better biodegradability; similar solvating power for this scaffold, though DCM often improves TLC resolution.
DMF vs MeCN/2-MeTHF: MeCN and 2-MeTHF offer easier workup and lower regulatory burden; DMF provides higher polarity but is harder to remove and has EHS concerns.
Dead-end derivatizations: Favor reversible protecting groups to reduce step count and waste.
Process suggestions:
Telescoping saponification→coupling in aqueous-organic biphasic systems can reduce solvent consumption.
Employ in-line base scavengers (e.g., resin-bound amines) to simplify neutralizations and reduce aqueous waste.
Pharmaceutical Uses
No pharmacopeial status or excipient role is specified for this item; it is supplied for research and laboratory synthesis only.
General formulation context (non-clinical, literature-based):
As a synthetic intermediate: The ethyl ester can serve as a temporary protecting group for the corresponding acid, facilitating extractions and chromatographic handling during medicinal chemistry route scouting.
Prodrug considerations: While alkyl esters are sometimes used as pro-moieties to modulate lipophilicity and permeability, no claims are made for this specific compound. If such strategies are explored in preclinical research, confirm hydrolysis rates and stability in simulated fluids.
Salt and solid form: The free phenolic OH allows potential formation of phenolate salts for process studies; usually, neutral forms are preferred for formulation-like solubility screening.
If your work requires compliance with pharmacopeial monographs, stability studies (ICH), or excipient compendial tests, obtain a lot-specific CoA and conduct in-house qualification; this catalog item has no stated pharmaceutical grade.
Physical Properties
Item-specific numerical specifications (density, UV cutoff, residual water/metals, etc.): Not specified for this item; refer to CoA/Spec Sheet.
Literature/estimation-based context (for reference; not product specifications):
Physical state: Phenoxyacetate esters of this type are typically low-melting solids or colorless to pale oils at ambient temperature; the presence of a free phenolic OH may increase crystallinity relative to fully etherified analogs.
Solubility profile (qualitative):
Organic solvents: Expected to be soluble in medium-polarity solvents (EtOAc, acetone, THF, MeOH), chlorinated solvents (DCM, CHCl3) and aromatic hydrocarbons (toluene). Limited solubility in aliphatic hydrocarbons (hexanes) due to polar functionality.
Aqueous: Low intrinsic water solubility at neutral pH; solubility increases in basic aqueous media via phenoxide formation and/or after saponification of the ethyl ester to the carboxylate salt.
Acid/base behavior: Phenolic pKa for para-phenoxy-substituted phenols is typically ~9.8–10.5 (literature, general range). The ethyl ester is not ionizable but can be hydrolyzed to the corresponding acid (typical pKa for aryloxyacetic acids ~3–4; literature ranges).
Partitioning: Expect moderate lipophilicity (logP for analogous phenoxyacetate esters often ~1.5–2.5; literature context).
Handling-relevant notes (general): The phenolic OH can engage in hydrogen bonding; solutions may show modest UV absorption due to the phenyl chromophore (typical π–π* bands in the 200–280 nm region; literature). For analytical parameters required for methods validation, consult the product CoA.
Quality and Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/Inhibitors: None indicated in the product data. If critical for your application (e.g., trace acid/base sensitivity, polymerization studies), confirm absence/presence on the CoA.
Guidance on grade meaning and analytical expectations (general):
For synthetic intermediates such as aryl phenoxyacetate esters, catalog grades often target high assay with controlled residual solvents, and may be suitable for multi-step synthesis, SAR campaigns, or materials science. Where HPLC/LC–MS work is intended, a “≥98% (HPLC)” or “HPLC grade” designation (when present) indicates impurities minimized for chromatographic baselines and UV transparency; confirm with the specific CoA.
Trace metal content, water content (Karl Fischer), and acid/base numbers are application-dependent and not specified here. For moisture-sensitive transformations (e.g., acid chlorides or isocyanate couplings post-saponification), consider in-house drying or azeotropic removal of water and verify by KF.
Identity confirmation: Expect standard techniques such as 1H/13C NMR, IR, and HRMS on request. For regulated workflows, request lot-specific analytical packages (CoA, CoC) and impurity profiles.
If your use requires specific parameters (UV cutoff, residual solvents, enantiopurity—achiral here), please contact Aladdin Scientific for a lot-specific CoA.
Reaction and Applications
This molecule is a versatile bifunctional building block combining a para-phenolic OH with an aryloxyacetate ethyl ester. Typical applications (general chemistry knowledge; expand per your route):
Ester manipulation:
Saponification to 2-(4-hydroxyphenoxy)acetic acid under basic conditions (NaOH, KOH; MeOH/H2O or THF/H2O, 0–25 °C). The acid can be converted to acid chlorides (SOCl2, (COCl)2) or directly coupled to amines (EDC/HOBt, HATU) to give amides.
Transesterification to alternative esters (Fischer, acid-catalyzed; or base-catalyzed with ROH in toluene/Dean–Stark or MeOH/EtOH under reflux). Protect the phenol as needed to suppress side etherification.
Phenolic OH derivatization:
O-Alkylation (Williamson ether synthesis) using alkyl halides or sulfonates with K2CO3/Cs2CO3 in acetone/MeCN/DMF. Phase-transfer variants (K2CO3, TBAB, toluene/H2O) are effective.
O-Acylation or carbamate formation with acyl chlorides/anhydrides or chloroformates in DCM/pyridine or with catalytic DMAP.
Mitsunobu reactions to install sensitive alkoxy groups (PPh3/DIAD or DEAD) where phenol acidity aids conversion.
Aryl functionalization downstream:
Electrophilic substitutions directed by the para substituents (nitration, sulfonylation) often proceed at the ortho positions; protect or account for the phenolic directing effects.
Use in library and SAR work: The aryloxyacetic acid motif is common in agrochemical and medicinal chemistry scaffolds. Retrosynthetically, the ester can be introduced early to control polarity and facilitate chromatographic handling, then switched to acid/amide late-stage.
Practical tips:
Control moisture for coupling steps after saponification.
Monitor for intramolecular transesterification or over-alkylation under strongly basic, high-temperature conditions.
Reaction Conditions
The following are general literature-style conditions for typical transformations of this scaffold; they are provided as guidance and are not product specifications:
Base-catalyzed saponification (to acid):
Conditions: 1–2 equiv NaOH or KOH in MeOH/H2O (4:1 to 1:1) or THF/H2O at 0–25 °C.
Time: 0.5–6 h depending on substrate loading and temperature.
Workup: Quench into cold 1 M HCl to pH ~1–2, extract with EtOAc, dry, and concentrate. Typical isolated yields for analogous esters: 85–98% (literature ranges).
Williamson ether synthesis on phenol:
Base: K2CO3 (2–3 equiv) or Cs2CO3; solvent: acetone or MeCN; temperature: reflux (acetone) or 50–80 °C (MeCN).
Electrophile: alkyl bromide/iodide or tosylate (1.2–1.5 equiv); catalytic KI can accelerate.
Time: 2–16 h. Typical yields for clean substrates: 60–90% (literature ranges). Protect the ester if very strong bases (NaH) are used.
O-Acylation (forming aryl esters/carbamates):
Reagents: Acyl chloride/anhydride or chloroformate (1.1–1.5 equiv) with Et3N or pyridine and cat. DMAP in DCM at 0–25 °C.
Time: 0.5–4 h. Typical yields: 70–95%.
Ester reduction (to aldehyde/alcohol):
DIBAL-H (1.5–2.0 equiv) in toluene or CH2Cl2 at −78 to −20 °C to stop at aldehyde; quench carefully.
LiAlH4 (1–2 equiv) in THF at 0–25 °C to convert to primary alcohol; protect phenol (e.g., as acetate/benzyl) beforehand. Yields often 60–90% (literature).
Always run small-scale trials and monitor by TLC/LC–MS. Adjust equivalents/temperature to your substrate and impurity profile.
Safety and Handling
Hazard classification: Not specified for this item; refer to the SDS for authoritative information. No GHS signal word, hazard statements, or pictograms are provided in the product data.
General laboratory safety guidance for aryl phenoxyacetate esters with phenolic OH (informational, not a substitute for SDS):
Likely hazards: Phenolic compounds are commonly irritants to skin/eyes and may cause respiratory irritation if aerosolized. Esters may cause mild irritation. Avoid inhalation of vapors/aerosols and contact with skin/eyes.
Personal protective equipment: Use safety glasses or goggles, lab coat, and appropriate chemically resistant gloves (e.g., nitrile). Employ local exhaust ventilation when weighing or transferring powders or handling concentrated solutions.
Handling: Avoid contact with strong bases and strong acids if hydrolytic stability is required; both catalyze ester cleavage. Avoid strong oxidizers. Phenolic OH may form salts with strong bases.
First aid (overview):
Skin/eye contact: Rinse cautiously with water for several 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/cleanup: Absorb small liquid spills with inert material; for solids, avoid dust formation. Collect in appropriate container for disposal according to local regulations.
Fire safety: Organic compound; use standard extinguishing media (CO2, dry chemical, foam). Combustion may produce CO/CO2 and phenolic vapors.
Always consult the product’s SDS for definitive hazard, exposure limits, and emergency response information.
Solvent Selection
Solubility and polarity guidance (general chemistry knowledge):
Polarity class: Moderately polar organic compound with both H-bond donor (phenolic OH) and multiple acceptors (Ar–O–, C=O). Often behaves well in medium-polarity solvents.
Recommended solvents for dissolution and processing:
Weak: Aliphatic hydrocarbons (hexanes/heptane) unless co-solvent is used.
Aqueous media: Limited solubility at neutral pH; solubility increases under basic conditions (phenoxide formation) or after saponification to the carboxylate salt. For biphasic reactions, phase-transfer catalysts can aid O-alkylation from the phenolic site.
When to choose specific solvents (practical tips):
Ester hydrolysis (saponification): Aqueous MeOH/THF with NaOH or KOH to access the acid; maintain temperature control to avoid transesterification side-products.
Phenolic derivatization (etherification/acylation): Polar aprotic solvents (acetone, DMF, MeCN) with K2CO3 or Cs2CO3; DCM/pyridine or DCM/Et3N for acylations.
Purification: Normal-phase silica with EtOAc/hexanes or DCM/MeOH gradients; protect phenolic OH if severe tailing occurs (add 0.1% AcOH or Et3N to the eluent as needed).
Comparison notes:
DCM/CHCl3 give excellent solubility and TLC response but consider greener alternatives (EtOAc, 2-MeTHF) where feasible.
For scale-up, EtOAc or 2-MeTHF often provide better EHS profiles while maintaining solubility.
Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
General storage guidance for phenolic aryloxyacetate esters:
Store tightly closed in a dry, well-ventilated area away from strong acids/bases and oxidizing agents. Phenolic OH can slowly react with strong bases/acylating agents; segregate accordingly.
Protect from prolonged exposure to moisture if hydrolytic stability is critical; although ethyl esters are reasonably stable, avoid storing in damp environments.
For long-term storage, an inert atmosphere (nitrogen/argon) and amber container are prudent to minimize oxidative discoloration of phenolic materials.
Reconstitution/handling:
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Dissolution: Readily dissolves in common organic solvents such as DCM, EtOAc, MeOH, acetone, THF, and DMF (general guidance). Warm gently (≤40 °C) and sonicate if needed. Filter through PTFE if particulates are observed.
Freeze–thaw: Not applicable; store as received. If preparing stock solutions, aliquot and store in sealed vials to limit evaporation and moisture ingress.
Always consult the lot-specific CoA/SDS for stability, purity, and safety information. Research Use Note: For research use only.
Structure and Identity
Ethyl 2-(4-hydroxyphenoxy)acetate is an aryl phenoxyacetate bearing a free para-phenolic OH and an ethyl ester at the α-oxygenated side chain.
Item identifiers (Product Data)
SKU: E727371
CAS: 20872-28-0
CID: 13187337
InChIKey (as provided): 273234
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed structure data (for reference; not product specifications)
Molecular formula (calculated from structure): C10H12O4
Molecular weight (calculated): 196.20 g/mol
Structural features (general description)
Aromatic ring: para-disubstituted benzene bearing a phenolic OH at the 4-position.
Ether linkage: phenoxy–CH2– linkage (Ar–O–CH2–) connecting the ring to the acetate side chain.
Carboxylate ester: ethyl ester of a 2-aryloxyacetic acid [–CH2–C(=O)–O–CH2CH3].
Hydrogen-bond functionality: one phenolic hydrogen-bond donor (–OH) and multiple acceptors (phenoxy O and carbonyl O atoms).
2D description in words: an ethyl ester [–O–CH2CH3] attached to a carbonyl [C(=O)] linked to a methylene [–CH2–] that is etherified to the para position of a phenyl ring bearing a free phenolic OH opposite the ether substituent (para orientation). No stereogenic centers; achiral.
Synthetic Utility
Functional group set and retrosynthetic handles make Ethyl 2-(4-hydroxyphenoxy)acetate a practical node in multistep routes:
Dual orthogonality:
Phenolic OH: amenable to etherification (Williamson), esterification/carbamylation, sulfonylation (tosylate/mesylate), and Mitsunobu-type alkylations; can be temporarily protected (Ac, Bn, TBDMS, carbonate) to direct chemoselectivity elsewhere.
Ethyl ester: convertible to acid, amide, or alcohol (via reduction) enabling branch-point diversification.
O-alkylation with alkyl halides/tosylates (K2CO3, Cs2CO3, NaH) to generate dialkyl aryl ethers without disturbing the ethyl ester.
Reduction (DIBAL-H at −78 to −20 °C) to the corresponding aldehyde, or LiAlH4/NaBH4 (with activation) toward alcohols; protect phenol as needed.
Cross-coupling on the ring is not directly accessible but can be enabled after installing halogens via electrophilic aromatic substitution.
Strategy notes:
Use selective protection to avoid competing O- vs C-alkylation and to minimize chromatographic tailing.
The para orientation simplifies NMR analysis and aids regioselective downstream substitution (e.g., ortho to the phenoxy linkage).
The aryloxyacetic linker can act as a spacer in linkouts for fragment growing or PROTAC-like constructs (post-conversion to amide/acid).
Workup/purification: Neutralize carefully after base-mediated steps to avoid premature ester hydrolysis; add a few drops of AcOH to silica eluents to reduce phenol tailing.
Target Specificity
Not applicable. This product is a small-molecule chemical building block, not a biological macromolecule or affinity reagent. No antigen/epitope, species reactivity, clone, or isotype information applies.
We use cookies to ensure the website functions properly and, where permitted, to improve your experience. You can manage your preferences at any time in Settings. Learn more in our Cookie Policy.
Shall we send you a message when we have discounts available?
Remind me later
Thank you! Please check your email inbox to confirm.
Products are supplied to verified businesses, institutions, and qualified professionals for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
