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Cité dans 0 publications à comité de lecture couvrant la chromatographie, la synthèse organique et les réactions de couplage croisé.

Spécifications

Synonymes

Spécifications et pureté

≥95%

Conditions de stockage de stockage

Room temperature

Expédié en

Normal

Pureté

≥95%

Noms et identifiants

Pubchem Sid

488194932

Sourires canoniques

CCOC1=CC=CC(=C1C(=O)OCC)O

IUPAC Name

ethyl 2-ethoxy-6-hydroxybenzoate

InChIKey

RWBODKGPEZVFRX-UHFFFAOYSA-N

INCHI

1S/C11H14O4/c1-3-14-9-7-5-6-8(12)10(9)11(13)15-4-2/h5-7,12H,3-4H2,1-2H3

Isomères SMILES

CCOC1=CC=CC(=C1C(=O)OCC)O

WGK Allemagne

Poids moléculaire

210.23

Reaxy-Rn

6596378

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=6596378&ln=

Documentation

📋 Fiche de données de sécurité (FDS)

Document complet couvrant les dangers, la manipulation, le stockage et la conformité réglementaire.

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✅ Certificat d'analyse (COA)

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Données avancées

Taxonomic Classification

Taxonomy Tree

Kingdom Organic compounds
- Superclass Benzenoids
  - Classe Benzene and substituted derivatives
    - Subclass Benzoic acids and derivatives
      - Level5 Benzoic acid esters
        Level6 o-Hydroxybenzoic acid esters

Kingdom	Organic compounds
Superclass	Benzenoids
Classe	Benzene and substituted derivatives
Subclass	Benzoic acids and derivatives
Intermediate Tree Nodes	Benzoic acid esters
Direct Parent	o-Hydroxybenzoic acid esters
Alternative Parents	Salicylic acid and derivatives Phenoxy compounds Phenol ethers Benzoyl derivatives Alkyl aryl ethers 1-hydroxy-4-unsubstituted benzenoids 1-hydroxy-2-unsubstituted benzenoids Vinylogous acids Carboxylic acid esters Organic oxides Hydrocarbon derivatives
Molecular Framework	Aromatic homomonocyclic compounds
Substituents	O-hydroxybenzoic acid ester - Salicylic acid or derivatives - Phenoxy compound - Benzoyl - Phenol ether - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Alkyl aryl ether - Phenol - Vinylogous acid - Carboxylic acid ester - Ether - Carboxylic acid derivative - Organooxygen compound - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Aromatic homomonocyclic compound
Description	This compound belongs to the class of organic compounds known as o-hydroxybenzoic acid esters. These are benzoic acid esters where the benzene ring is ortho-substituted with a hydroxy group.
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. DOI: 10.1186/s13321-016-0174-y

Structure 3D

Certificats (CoA, COO, BSE/TSE et tableau d'analyse)

C of A & Other Certificates(BSE/TSE, COO):

Analytical Chart:

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3 results found

Lot Number	Certificate Type	Date	Article
B23011098	Certificate of Analysis	Nov 10, 2022	E340702
B23011100	Certificate of Analysis	Nov 10, 2022	E340702
C2505167	Certificate of Analysis	Nov 10, 2022	E340702

Propriétés chimiques et physiques

Point de fusion (°C)	60° C (lit.)
Poids moléculaire	210.230 g/mol
XLogP3	2.700
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	5
Exact Mass	210.089 Da
Monoisotopic Mass	210.089 Da
Topological Polar Surface Area	55.800 Å²
Heavy Atom Count	15
Formal Charge	0
Complexity	205.000
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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Application Protocols

No tested biological assay protocols (e.g., WB, IHC, IF, FC) are applicable to this small-molecule reagent. For synthetic/analytical use, consider the following general lab protocols:

Preparation for reactions: Dry under high vacuum at room temperature if moisture-sensitive chemistry is planned. Dissolve in a suitable organic solvent (e.g., EtOAc, DCM, THF, MeCN) at the desired concentration immediately before use.
Analytical characterization: Verify identity and purity by 1H/13C NMR, IR (ester C=O ~1735–1715 cm−1; phenolic O–H broad stretch), LC–MS (ESI), and HPLC/GC as appropriate. For phenolic OH, titration or derivatization (e.g., TMS) can aid GC analysis.
Workup and purification: For basic/acidic reactions, neutralize carefully to avoid premature ester hydrolysis. Employ silica gel chromatography with appropriate modifiers if phenolic tailing occurs.

Note: These are general recommendations for small-molecule handling; consult Reaction Conditions and Synthetic Utility for transformation-specific guidance.

Biological Roles

No biological/biochemical activity data are provided in the Product Data for this item. The following is general context for the salicylate scaffold and is not specific to this compound.

Salicylate motif: Ortho-hydroxybenzoates are common in plant secondary metabolites and can participate in metal chelation via the o-phenol/carboxylate pair once deprotonated.
Physicochemical profile: The presence of a phenolic OH and an ester typically yields limited aqueous solubility and moderate lipophilicity. Such features can influence membrane affinity and partitioning in biomimetic systems.
Reactivity in biological media (general): The ethyl ester can undergo hydrolysis in strongly acidic/basic environments or via esterases in biological systems; however, rates depend sensitively on substitution (the 6-ethoxy aryl ether may modulate electronic effects) and medium.
Use in research: Substituted salicylates are frequently employed as synthetic intermediates, ligands for coordination studies, or model substrates for studying ester hydrolysis or phenolic reactivity under biomimetic conditions.

Important: This product is supplied strictly for research and laboratory use. No claims are made regarding therapeutic activity, pharmacology, or clinical suitability. For any work involving biological systems, assess stability, hydrolysis propensity, and potential non-specific binding empirically.

Buffer Applications

This compound is not a buffering agent and is not typically used to prepare laboratory buffer systems. It lacks appropriate acid/base pairs with pKa values suited for conventional biological buffer ranges when maintained as an intact ester.

Practical guidance:

If experiments require aqueous handling (e.g., partitioning studies), select a compatible external buffer (e.g., phosphate, acetate, TRIS, HEPES) as appropriate for your pH range and ensure the compound is introduced via a co-solvent (DMSO/EtOH) at low percentage to avoid precipitation.
For kinetic hydrolysis studies, acetate (pH ~4–5) and phosphate/carbonate buffers (pH ≥7) may be used as media; the compound itself does not contribute buffering capacity.

Conclusion: See Reaction & Applications and Synthetic Utility sections for relevant uses of this compound in organic synthesis rather than buffer formulation.

Green Alternatives

While Ethyl 6-ethoxy-2-hydroxybenzoate is a target molecule/intermediate rather than a process solvent, greener choices relate to the solvents and reagents used when synthesizing or transforming it.

Greener solvent substitutions (literature/general guidance):

Replace dichloromethane/chloroform with ethyl acetate, 2-MeTHF, CPME, or toluene where reaction selectivity permits.
Prefer 2-MeTHF or CPME over THF for Williamson ether or acylation chemistry; they offer reduced peroxide concerns and improved sustainability metrics.
For ester hydrolysis/transesterification, use ethanol or isopropanol instead of methanol when feasible; or run in aqueous media with phase-transfer catalysis.

Reagent and process considerations:

Catalytic acylations using isobutyric anhydride or propionic anhydride with organocatalysts (DMAP) may reduce reliance on acid chlorides.
Employ carbonate bases (K2CO3, Cs2CO3) and phase-transfer catalysts to avoid strong bases/cryogenic conditions for O-alkylations.
Explore biocatalytic transesterification/hydrolysis (lipases) in green solvents or solvent-free conditions for selective modifications of the ester moiety.

Comparison snapshot (general):

THF vs 2-MeTHF: similar polarity and performance in many substitutions; 2-MeTHF is bio-derived, higher boiling, and less miscible with water, aiding workups.
DCM vs EtOAc: EtOAc is non-halogenated, biodegradable, and often effective for extractions and as reaction medium, though less inert to strong bases.

Note: Select solvents and conditions based on performance, safety, regulatory, and waste considerations aligned with your process constraints.

Pharmaceutical Uses

No pharmacopeial grade, excipient role, or formulation specification is provided in the Product Data for this item.

General R&D context (non-clinical):

Synthetic intermediate: Substituted salicylate esters are commonly used as intermediates en route to salicylic acids, amides, and salicylaldimines, which may be explored in medicinal chemistry campaigns. Ethyl 6-ethoxy-2-hydroxybenzoate can be hydrolyzed or further derivatized to generate analog libraries.
Impurity/reference standard: In API process development involving salicylate-like scaffolds, structurally related esters may be monitored as potential impurities or side-products. This material can serve as a reference standard if accompanied by suitable analytical characterization.
Excipients: No evidence or claim is made that this compound serves as an excipient. Verify regulatory status before any consideration outside basic research.

Key cautions:

Do not use for human or veterinary applications. For research use only (as per Product Data).
If intended as an analytical standard, define acceptance criteria (purity, water, residual solvents) and confirm via CoA and orthogonal analyses (qNMR, HPLC).

Physical Properties

Item-specific physicochemical specifications (mp, bp, density, refractive index, UV cutoff, residuals) are not supplied in the Product Data.

Melting point: Not specified for this item; refer to CoA/Spec Sheet.
Boiling point: Not specified for this item; refer to CoA/Spec Sheet.
Density: Not specified for this item; refer to CoA/Spec Sheet.
Refractive index: Not specified for this item; refer to CoA/Spec Sheet.
Water content (Karl Fischer), peroxides, metal content: Not specified for this item; refer to CoA/Spec Sheet.

General/literature-based expectations for this structural class (for method planning only):

Phase/appearance: Substituted salicylate esters with one additional alkoxy substituent are often low-melting solids or viscous oils; actual state depends on purity and temperature.
Solubility profile (literature/general): Poorly soluble in water; readily soluble in common organic solvents (EtOAc, acetone, CH2Cl2, THF, toluene, MeOH/EtOH) due to aromatic and ester/ether functionalities.
Acid–base behavior (general): Weakly acidic phenolic OH (salicylate motif) enables deprotonation in the presence of bases (e.g., alkoxides, carbonate, tertiary amines). The ethyl ester is neutral; aryl ether is non-basic.
Volatility: Lower volatility than simple ethyl salicylate due to added aryl–O–ethyl substituent; typically manageable under standard fume hood conditions.

Important: Use literature expectations only for preliminary planning. For precise specifications required for QC, purification design, or process safety, consult the item’s CoA/Spec Sheet and SDS.

Quality and Grades

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

Interpretation and guidance:

When grade/purity is unspecified, Aladdin typically provides a CoA that details assay method (e.g., GC, HPLC, qNMR), main component area %, and key impurities. Request the current CoA/Spec Sheet for batch-specific values.
Chromatography suitability: If you plan to use this compound as a reference standard, impurity profiling (isomers, residual solvents) and UV background in your analytical window (200–400 nm) should be verified. “HPLC grade” or “GC grade” would indicate tight control of UV cutoff/residuals; absent such claims, confirm fit-for-use analytically.
Stabilizers/inhibitors: None are listed in Product Data. If stabilizers are critical for your workflow, confirm their absence/presence in the CoA.
Trace metals/ions: Not specified for this item; refer to CoA/Spec Sheet. For metal-catalyzed transformations (e.g., C–O or C–C cross-coupling on this scaffold), consider pre-treating or re-purifying if metal sensitivity is expected.
Water/peroxide content: Not specified for this item; refer to CoA/Spec Sheet. Although aryl ethers are not peroxide-forming like dialkyl ethers, routine peroxide testing is unnecessary; however, moisture control is advisable for base- or acid-sensitive steps.

Recommendation: Define acceptance criteria aligned with your intended application (synthesis vs. analytical standard) and verify via CoA and incoming QC.

Reaction and Applications

As an ortho-hydroxy ethyl benzoate bearing a 6-ethoxy substituent, Ethyl 6-ethoxy-2-hydroxybenzoate is a versatile building block for salicylate-derived scaffolds.

Representative application spaces (literature/general):

Phenolic derivatization:
- O-acylation: formation of salicylate esters/carbamates (acyl chlorides/anhydrides with base or DMAP). The ortho OH can be selectively functionalized due to its enhanced acidity and potential intramolecular H-bonding.
- O-alkylation: Williamson ether synthesis under basic conditions (NaH, K2CO3/phase-transfer), enabling protection or diversification at O-2.
Ester transformations:
- Hydrolysis/saponification to the corresponding 2-hydroxy-6-ethoxybenzoic acid (acid chloride accessible via SOCl2, oxalyl chloride).
- Transesterification (acidic or basic) to tune ester identity; aminolysis to yield amides.
Ring functionalization:
- Electrophilic aromatic substitution at remaining positions (3,4,5). The combined directing effects of –OH (activating, ortho/para) and –OEt (activating, ortho/para) are moderated by the deactivating –CO2Et group; regioselectivity can often be steered by conditions and temporary protection of –OH.
Coordination chemistry:
- The salicylate motif (o-OH/CO2R) can chelate metals upon deprotonation, providing access to metal–ligand complexes or serving as a masked salicylic acid ligand precursor.

Practical tips:

Drying: If base-sensitive steps are planned, dry the material under high vacuum at ambient or mild temperature prior to use.
Protecting group strategy: The phenolic OH may require protection (e.g., benzyl, silyl) for certain electrophilic substitutions; conversely, transient acylation can control reactivity and regioselectivity.
Monitoring: 1H NMR signals for phenolic OH (often downfield, H-bonded) and ethyl groups (quartet/triplet) are diagnostic for conversion and selectivity.

Reaction Conditions

The following are literature/general conditions for common transformations of salicylate esters and should be adapted based on small-scale scouting. They are not item-specific specifications.

Phenolic O-acylation:
- Reagents: acyl chloride or anhydride (1.1–1.5 eq), base (triethylamine, pyridine), catalytic DMAP (0.05–0.1 eq).
- Solvent: DCM, EtOAc, toluene, or MeCN.
- Temperature/time: 0–25°C, 0.5–4 h. Typical isolated yields: 70–95% (substrate-dependent).
Phenolic O-alkylation (Williamson):
- Base: K2CO3 (2–3 eq) or NaH (1.1–1.5 eq) for more challenging alkyl halides.
- Solvent: acetone, MeCN, DMF, THF/2-MeTHF.
- Electrophile: primary alkyl halides/sulfates (1.2–1.5 eq).
- Temperature/time: reflux in acetone/MeCN (2–12 h) or 0–25°C with NaH (1–3 h). Yields commonly 60–90%.
Ester hydrolysis/saponification:
- Conditions: NaOH or KOH (1–3 eq) in MeOH/H2O or THF/H2O (pH >12) at rt–50°C, 1–6 h; or acid hydrolysis (HCl, H2SO4) under reflux in EtOH/H2O.
- Workup: acidify to pH ~2 to precipitate the salicylic acid derivative. Typical yields: 75–95%.
Ester reduction:
- DIBAL-H (1.5–2.0 eq) in toluene or DCM at −78 to −20°C to afford the aldehyde/alcohol (quench carefully); or LiAlH4 in THF (0–25°C) to the primary alcohol. Yields: 60–90%.
Electrophilic aromatic substitution:
- Halogenation (e.g., NBS/NCS) in AcOH or DMF at 0–25°C; nitration with HNO3/Ac2O (low temp) cautiously to manage regioselectivity.

Monitoring and purification:

TLC/HPLC with UV detection (254–280 nm). Phenolic hydrogen often appears downfield (δ ~10–12 ppm) in 1H NMR, useful for tracking O-functionalization.
Use buffered silica or add 0.1–1% Et3N to eluent to minimize phenol tailing.

Safety and Handling

GHS hazard classification, signal word, H/P statements, and pictograms are not provided in the Product Data for this item. Always consult the official SDS for authoritative safety information.

General safety considerations for substituted salicylate esters (guidance only):

Likely hazards: May cause skin/eye irritation; ingestion or inhalation of vapors/aerosols should be avoided. Phenolic OH can increase irritation potential relative to non-phenolic esters.
PPE: Use lab coat, safety glasses or chemical splash goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Handle in a fume hood.
Handling: Avoid breathing vapors/mist. Prevent contact with strong bases (will promote transesterification/saponification) and strong acids (may catalyze hydrolysis). Keep away from strong oxidizers.
Stability: Esters may hydrolyze under acidic or basic conditions; phenolic OH can undergo O-acylation/alkylation in the presence of strong electrophiles. Aryl ethers are generally stable under neutral conditions.
First aid (overview; see SDS):
- Inhalation: Move to fresh air; seek medical attention if symptoms persist.
- Skin: Wash with soap and water; remove contaminated clothing.
- Eyes: Rinse cautiously with water for several minutes; remove contact lenses if present and easy to do.
- Ingestion: Rinse mouth; do not induce vomiting; seek medical advice.
Fire safety: Combustible organic compound; use CO2, dry chemical, or foam. Thermal decomposition may produce irritating fumes.

Storage and transport per Product Data:

Storage: Room temperature.
Shipped: Normal conditions.

Note: This product is for research use only.

Solvent Selection

This product is a functionalized aromatic ester (solid/liquid, depending on conditions), not a solvent. Solvent choice concerns its dissolution, reaction media, and purification.

General solubility/miscibility guidance (literature/class-based):

Good solvents: EtOAc, acetone, acetonitrile, THF/2-MeTHF, DCM/CHCl3, toluene, MeOH/EtOH, DMF/DMSO.
Poor solvents: Water and very nonpolar alkanes (hexanes) may show limited solubility; however, mixtures (hexanes/EtOAc or heptane/EtOAc) are often effective for crystallization or flash chromatography.

Selection by use case:

Reaction media:
- Base-mediated O-acylation/alkylation of the phenolic OH: polar aprotic (DMF, DMAc, DMSO) or ethereal solvents (THF, 2-MeTHF) with appropriate base.
- Hydrolysis/transesterification of the ethyl ester: alcoholic solvents (MeOH/EtOH) with acid/base catalysis; for aminolysis, use toluene, MeCN, or neat amine with catalysts.
- Electrophilic aromatic substitution (EAS) on residual ring positions: nitrobenzene, DCM, or acetic acid depending on electrophile and conditions.
Purification:
- Flash chromatography: silica gel with hexanes/EtOAc or toluene/EtOAc gradients. The phenolic OH may tail; small % of TEA or use of buffered silica can improve band shape.
- Crystallization: explore EtOAc/hexanes, toluene/hexanes, or MeOH/water (salting out) if the material is solid.

Note on greener choices: Where possible, prefer 2-MeTHF over THF, EtOAc over DCM, and MeCN alternatives (e.g., EtOAc, IPA) when performance allows.

Storage and Reconstitution

Storage conditions (from Product Data): Store at room temperature.
Shipping (from Product Data): Shipped under normal conditions.

General storage guidance:

Container: Keep tightly closed in an inert, chemically compatible container (amber glass recommended) to minimize light exposure and adventitious moisture uptake.
Atmosphere: Not air-sensitive under normal conditions; for long-term storage, consider desiccation and, if frequently opened, an inert headspace to limit hydrolysis.
Stability: Esters are susceptible to hydrolysis under strong acidic/basic conditions; avoid storing near acids/bases or moisture sources. The aryl ether is typically robust.
Shelf life: Not specified for this item; refer to CoA/Spec Sheet.

Reconstitution/handling:

This is a neat organic compound. No reconstitution is required. For solution preparation, dissolve in a compatible organic solvent (e.g., EtOAc, DCM, THF, MeCN, ethanol) at the desired concentration immediately before use.
Freeze–thaw: Not applicable. If preparing stock solutions for analytical use, store aliquots in sealed vials at controlled temperature to prevent solvent loss and concentration drift.

Research use note: For research use only, as indicated in the Product Data.

Structure and Identity

Ethyl 6-ethoxy-2-hydroxybenzoate is a substituted salicylate ester featuring a phenolic OH at the ortho position relative to an ethyl ester, and an additional ethoxy substituent at the 6-position of the aromatic ring.

SKU: E340702
CAS: 154364-61-1
CID: 4616897
InChIKey (from Product Data): 327588
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula (literature/computed, based on name): C11H14O4
Molecular weight (literature/computed): ~210.22 g/mol

Structural features (general description):

Core ring system: monosubstituted benzene bearing a salicylate motif (2-hydroxybenzoate).
Functional groups: one phenolic hydroxyl (o to the ester), one ethyl ester (–CO2Et), and one aryl–O–ethyl ether at the 6-position.
Substitution pattern: 1 (carboxylate carbonyl) – 2 (phenolic OH) – 6 (ethoxy). The 2- and 6-substituents create steric congestion about the ortho sites.
Stereochemistry: none (achiral, no stereogenic centers).
2D description: a benzene ring with an ethyl ester (–CO2CH2CH3) at C-1, a phenolic –OH at C-2 (ortho), and an –OCH2CH3 substituent at C-6 (para to the phenol across the ring). The phenolic OH can engage in intramolecular H-bonding to the ester carbonyl, typical of salicylates.

Notes:

Any identifiers not present in Product Data are provided as literature/computed references for general context only; consult the CoA/Spec Sheet for definitive item-specific identifiers.

Synthetic Utility

Functional group ensemble and reactivity map:

Phenolic OH (o to ester): amenable to O-acylation, O-alkylation, carbonate/carbamate formation; can be transiently protected (Bn, silyl, MOM) to direct ring functionalization.
Ethyl ester: convertible to acid, acid chloride, amide, alcohol (via reduction), or other esters (transesterification). The ortho phenol can direct certain transformations via chelation or H-bonding.
Aryl ether at C-6 (–OEt): generally robust; can be cleaved under strong Lewis acidic or reductive conditions, but typically retained as an electron-donating substituent influencing EAS.

Named/typical transformations (literature/general):

Saponification to 2-hydroxy-6-ethoxybenzoic acid, followed by coupling (EDC/HOBt, HATU) to give amides or ureas.
O-alkylation at the phenol via Williamson ether synthesis (NaH/THF or K2CO3/acetone) to install protecting or functional groups (allyl, benzyl, propargyl) enabling further diversification (e.g., cross-coupling after benzylic deprotection to phenol).
Selective reduction of the ester (DIBAL-H, LiAlH4) to the benzyl alcohol, followed by oxidation (Dess–Martin, PCC) to the aldehyde, enabling access to salicylaldehyde-type derivatives without needing formylation on the ring.
Directed ortho metalation is curtailed by substitution density, but halogenation/nitration at residual positions (3–5) is feasible under controlled EAS conditions; subsequent cross-coupling expands scope.

Retrosynthetic value:

Serves as a masked salicylic acid with built-in activation; the ethoxy at C-6 pre-sets electronics/sterics, supporting structure–activity exploration in SAR campaigns or ligand design.

Target Specificity

Not applicable. This product is a small-molecule chemical reagent and does not have biological target specificity, antigen/epitope information, clone, or isotype. No application-specific targeting data are provided in the Product Data.

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Ethyl 6-ethoxy-2-hydroxybenzoate - ≥95% , CAS No.154364-61-1

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